🗺️ What To Do This Weekend

Friday October 23, 2026

• 🥫 Island Grown Initiative’s Serving Hands at 66 William Street, Vineyard Haven, 11:30a-1p / More Info

• 🎶 Fire and Song at Old Whaling Church, 7-8:30p / More Info / $60; $100 sponsor and reception
  Pianist Joel A. Martin and vocalist Theresa Thomason perform a benefit concert for the MV Diversity Coalition and its Living Legends Project, blending classical, jazz and African American musical traditions.

• 🎹 An Evening with Matt Nakoa at MV Playhouse, 7p / More Info / $25
  Award-winning composer, pianist and singer-songwriter Matt Nakoa brings a genre-spanning performance ranging from classical piano to folk, rock and original music.

Saturday October 24, 2026

• 🥕 West Tisbury Farmers Market at Agricultural Hall, West Tisbury, 9a-12p / More Info / Free

• 🎨 Children’s Saturday Crafting: Halloween with Helen Hall at Featherstone Center for the Arts, 10a-12p / More Info / $40

• 🎃 Sixth Annual Harvest Festival at Agricultural Hall, 10a-2p / More Info / Free
  The MV Agricultural Society’s annual fall celebration fills the Ag Hall grounds with pumpkin carving, face painting, a clothing swap, a hay bale maze, scavenger hunt, bulb planting, touch-a-tractor activities, oat pools and mud kitchens, cow chip bingo, local food vendors and more.

  • Timed highlights include the West Tisbury Farmers Market and live music by Blues Switch from 9a-12p, a meet-a-beekeeper session from 10a-12p, indigo dyeing at 10:30a, 12p and 1:30p, sack races at 10:30a, an MV Shellfish Group shucking lesson and demo at 11a, corn husking at 11:30a, music by the Flying Elbows from 12-1p, an “Ask Me Anything” with gardener Faren Osnoss from 12-2p, a squash toss at 12:30p, square dancing from 1-2p and a pie-eating contest at 2p.

• 🥞 Brunch Under the Tent at Farm Neck Golf Club, 10a-12:30p / More Info / $150

• 🔪 Introduction to Knife Sharpening at Stillpoint, 10:30a-12:30p / More Info / $75

• 🎃 Pumpkin Decorating at Town MV at Town MV, 12-3p / More Info / $25
  Spend the afternoon decorating a pumpkin with supplies included. Admission also includes a choice of one cocktail, snack or kids’ meal.

• ⛳ Steere the Course Mini Golf Fall Festival at Steere the Course Mini Golf, 12-4p (Sun too)
  A two-day fall festival with pumpkins for sale, pumpkin painting, food and seasonal specials, festival games and trick-or-treating.

• 🖼️ Exploring Printmaking with Allison Doherty at Featherstone Center for the Arts, 1-4p / More Info / $65

• 🎈 Children’s Day at MVRHS, 1-4p / More Info
  Inspired by the Brazilian tradition of Children’s Day, this community celebration welcomes Island families for games, activities, snacks, treats, raffles and more.

• 🏳️‍🌈 Teen Pride Party at Vineyard Haven Public Library, 7-10:30p / More Info / Free

• 🎶 Thistle at MV Playhouse, 7p / More Info / $25

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Sunday October 25, 2026

• 🧙 The Witching Hour: A Paddle Parade of Witchy Fun at Collin’s Beach, 9-10a / More Info / Free
  Costumed witches, warlocks and other paddlers take to kayaks, SUPs and canoes for a playful paddle toward Edgartown Lighthouse. A $20 donation to the Vineyard Cancer Support Group is suggested.

• 👻 Edgartown’s Happy Haunting at Downtown Edgartown, 10a-1p / More Info / Free
  Families can dress up and trick-or-treat from participating businesses throughout downtown Edgartown during this annual Halloween tradition.

• 🎶 Kirtan, Live Music, Call and Response Chanting with Bhakti at West Tisbury Public Library, 12-1p / More Info

• 🍬 Trunk or Treat at Oak Bluffs Council on Aging (21 Wamsutta Avenue.), 2-4p

• 🎃 Trunk or Treat Fundraiser at Martha’s Vineyard Public Charter School, 2:30-4p / $25 per family
  The MVP Charter School PTO hosts an afternoon of trick-or-treating, face painting, wagon rides, pumpkin painting and more. Some activities carry an additional charge; attendees are asked to park at Up-Island Cronig’s.

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Thank you for being here, onto this week!

🗺️ What To Do This Weekend

Friday October 16, 2026

• 🎣 Martha's Vineyard Striped Bass and Bluefish Derby @ Derby Headquarters, Dock Street, Edgartown, Daily weigh-ins 8-10a & 7-9p / More Info (All Weekend)

• 🎨 Bass in the Grass @ The Carnegie, Edgartown / More Info / Free (All Weekend)

• 🧘 Self Care Club @ West Tisbury Public Library, 3:15-4:15p / More Info / Free

• 🎬 8th Annual Women in Film Festival @ MV Film Center, Begins 4p (Sat & Sun too) / More Info
  The MV Film Society’s three-day festival celebrates women in front of and behind the camera with films told from women’s perspectives, plus select filmmaker Q&As.

• 🎥 MUSK The Definitive Documentary About the World’s Richest Man @ Strand Theatre, 5:30p (Sat 12p & 5:30p; Sun 3p too) / More Info

• 🏈 Varsity Football Home Game @ Martha’s Vineyard Regional High School, 6-8p / More Info / Free, donations welcome

• 😂 Comedy with TBD Improv @ The Barn, Bowl & Bistro, 6:30-8p / More Info / $17
  Expect a completely unscripted, often racy improv show upstairs at The Barn.

Saturday October 17, 2026

• 🥕 West Tisbury Farmers Market at Agricultural Hall, West Tisbury, 9a-12p / More Info / Free

• 🏃 MV Brunch Run and Walk 5K & 10K @ Katama General Store, 8-10:30a / More Info / $11.60-$48.70
  Choose from a youth one-mile race at 8a, 10K at 8:15a, or 5K at 8:30a, with brunch included in select registrations; there is no parking at Katama General Store, so use the Edgartown School lot or limited shuttle service.

• 🎨 Children’s Saturday Crafting: Halloween with Helen Hall @ Featherstone Center for the Arts, 10a-12p / More Info / $40

• 🎃 Ponies and Pumpkins @ Misty Meadows Equine Learning Center, 10a-12p / More Info / Free
  Bring the family for kids’ games, fall crafts, face painting, pumpkin decorating, and a chance to meet the horses.

• 🍳 Found Foods: A Hands-On Culinary Experience @ The FARM Institute, 10:30a-12:30p / More Info / $45

• 🎃 Annual Pumpkin Festival @ Morning Glory Farm, 10:30a-2:30p / More Info
  Celebrate fall with hayrides, a pumpkin trebuchet, Touch-a-Tractor, maize maze, haunted greenhouse, pumpkin decorating, kids’ games, animals, live music, a pie-eating contest, seasonal food, and more.

• 🧘 Sound Bath with Trish Ginter @ Edgartown Public Library, 11:30a-12:30p / More Info

• 👻 MVLA Halloween Costume Swap @ West Tisbury Public Library, 12-1:30p / More Info

• 🛠️ SparkMVxTradesUp @ Agricultural Hall, 12-4p / More Info / Free

• 🧩 Piece by Piece: Library Puzzle Showdown @ Oak Bluffs Public Library, 1-3p / More Info

• 🫖 League of Women Voters of MV: Tea Time! @ Martha’s Vineyard Museum, 3p / More Info

Sunday October 18, 2026

• 🎣 MV Striped Bass & Bluefish Derby Awards Ceremony @ Farm Neck Golf Club, 11a / More Info
  The Derby wraps up with its annual awards ceremony, beginning with Junior Awards at 11a followed by Adult, All-Tackle, and Fly Rod Awards at 1p.

• 🚶 2026 MV CROP Hunger Walk @ St. Augustine’s Church, 1:30-3:30p / More Info
  Join the 36th annual three-mile community walk from St. Augustine’s Church to the Lagoon Bridge and back, with shorter route options available and proceeds supporting local and global hunger relief.

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⏱️ This Week on MVacay

🗺️ What To Do This Weekend

Friday October 9, 2026

• 🎣 Martha's Vineyard Striped Bass and Bluefish Derby @ Derby Headquarters, Dock Street, Edgartown, Daily weigh-ins 8-10a & 7-9p / More Info (All Weekend)

• 🎨 Bass in the Grass @ The Carnegie, Edgartown / More Info / Free (All Weekend)

• 🌽 Morning Glory Farm Corn Maze at Morning Glory Farm, daily 8:30a-5:30p / More Info / $5 (All Weekend)

• 🧘 Self Care Club at West Tisbury Public Library, 3:15-4:15p / More Info / Free
  A weekly program for ages 8+ focused on creative, restorative self-care activities and healthy habits.

• 🎬 Fall Film Showcase: The Incomer at Grange Hall, 7p / More Info / Pay what you can
  Part of Circuit Arts’ Fall Film Showcase, with relaxed couch seating at the Grange Hall. Advance tickets are available online.

Saturday October 10, 2026

• 🏃 Oak Bluffs School Annual Fall 5K Run & Walk at Washington Park, 8:30a / More Info / $30

• 🥕 West Tisbury Farmers Market at Agricultural Hall, West Tisbury, 9a-12p / More Info / Free

• 🎃 Fall on the Farm at The FARM Institute, 10a-12p / More Info / $25 per family
  Family admission covers up to five guests and one pumpkin, with wagon rides, crafts, a scavenger hunt and barnyard animals. Pre-registration is encouraged because pumpkins are limited; the event is weather dependent.

• 🍂 Harvest Festival at Oak Bluffs Public Library, 10-11:30a / More Info / Free
  Held outdoors on the library lawn in partnership with Slough Farm, with cider, popcorn, crafts, activities and farm animals.

• 🌻 Vineyard Gardens Annual Harvest Festival at Vineyard Gardens, 10a-2p / More Info / Free
  Seasonal plants, nature crafts and fall projects include pumpkin bouquets, pinecone bird feeders and paperwhite planting.

• 🎨 Vineyard Artisans Fall Festival at Grange Hall, 10a-4p (Sun too) / More Info

• Warehouse Sales:

  • 🌸 Donaroma’s Floral Hard Goods Sale at Donaroma’s, 9a-5p (Sat & Mon too) / More Info

  • 🛍️ Bespoke Abode Warehouse Sale at Bespoke Abode, / More Info

  • 🏷️ Tracker Home Decor Annual Storage Unit Sale at 11 North Line Road, Edgartown, 10a-2p / More Info

  • 🪑 Second Treasures Annual Inventory Reduction Sale at Featherstone Center for the Arts, 10a-2p (Sun too) / More Info

• ✂️ Drop-In Crafts: DIY Reading Scratchers and Paint by Sticker at Aquinnah Public Library, 12-3p / Free

• 🌽 First Annual Cornhole Tournament at Nomans, 12-4p / More Info / $50 per team

• 🌿 Fall Wreath Workshop at Juniper, 1-3p / More Info / $125 Call to Register

• 🎬 Fall Film Showcase: Your Mother Your Mother Your Mother at Grange Hall, 7p / More Info / Pay what you can

• 🎥 American Doctor with Dr. Feroze Sidhwa at Martha’s Vineyard Film Center, 7:30p / More Info / $15
  The documentary follows three physicians working amid the Gaza conflict and their advocacy in the U.S. The screening is followed by a discussion with humanitarian and trauma surgeon Dr. Feroze Sidhwa; doors open at 7p.

Sunday October 11, 2026

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free

• 🚗 Car-B-Q Classic Auto Show & Power Cruise at Winnetu Oceanside Resort, 11a-2p / More Info / Free
  The Power Cruise through Edgartown begins at 10a before the cars gather at Winnetu for the show, People’s Choice voting, barbecue and awards. Spectator admission is free.

• 🍽️ Season End All-You-Can-Eat Celebration at Nomans, 11a-until sold out / More Info / $25
  Nomans wraps up its 2026 season with an all-you-can-eat sendoff. Kids under 12 eat free; drinks are not included.

• 🌱 Create a Food Forest in Your Backyard at Beetlebung Farm, 1-2:30p / More Info / Free

• ✍️ Open Writing Hours at Featherstone Center for the Arts, 1-3p / More Info / Free

• 🔔 A Super Sound Bath with Priscilla Warner and Alison Leipzig at Stillpoint, 4-5p / More Info / $30-$60

• 🌳 Between the Oaks Outdoor Church at First Congregational Church of West Tisbury, 4:30-5:30p / More Info

• 🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free - Last of the Season

Monday, October 12, 2026 - Indigenous Peoples’ Day

• 🍽️ MV Local Wild Food Festival at Grange Hall, 12-5p / More Info
  Chef Billy Manson brings the Local Wild Food Challenge back to MV for an afternoon of culinary competition, wild food demos, outdoor cooking, live local music and Island artisans. Food and drinks will be available for purchase throughout the day.

• 💆 Spa Day at Tashmoo Farm, 1-5p / More Info

• 🪶 Sassafras Earth Education Indigenous Peoples Day at Felix Neck Wildlife Sanctuary, 2-3:30p / More Info / Free
  A community gathering honoring Wôpanâak people, culture and ancestral territory, with speakers and songs from the Black Brook Drummers.

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🗺️ What To Do This Weekend

Friday October 2, 2026

• 🎣 Martha's Vineyard Striped Bass and Bluefish Derby @ Derby Headquarters, Dock Street, Edgartown, Daily weigh-ins 8-10a & 7-9p / More Info All Weekend

• 🎨 Bass in the Grass @ The Carnegie, Edgartown, All Weekend / More Info / Free

• 🎨 First Friday Vineyard Haven at Downtown Vineyard Haven, All Day / More Info / Free
  A day of art, shopping and activities downtown followed by food, music, a bonfire and dancing at Owen Park.

  • 🛍️ First Friday VH Passport Challenge at Participating Businesses, All Day

  • 🎨 Daytime Art Market at Beach St. Ext., Art Hang at Althea Designs,10a-2p

  • 10a-2p / 🎵 Live Music at 5 Corners, 12p

  • 🎨 Evening Activities: Food Trucks, Live Painting, Beach Bonfire on the Hill at Owen Park, 5p-Dusk

  • 🥁 Upis Land Band from Main Street to Owen Park Beach, 6-6:30p

  • 🎵 Johnny Hoy and the Bluefish at Owen Park Beach, 7-8p

  • 🎧 Silent DJ Party with PathwaysARTS at Owen Park Beach, 8-10p

• 🎨 HERitage: A Multimedia Music and Arts Festival Honoring Historic Vineyard Women at Stillpoint, West Tisbury, 3-8p / More Info + Tickets / $15–$40
  Doors open at 3p for art showcases, food and henna, followed by music from 6-8p. Admission is sliding scale; advance tickets are available, drop-ins are welcome.

Saturday October 3, 2026

• 🥕 West Tisbury Farmers Market at Agricultural Hall, West Tisbury, 9a-12p / More Info / Free

• 🎸 LadyFest MV 2026 at Waban Park, Oak Bluffs, 1-9p / More Info + Tickets / $35
  Outdoor music festival featuring musicians, artisans, food and other vendors, with proceeds benefiting CONNECT to End Violence. Gates open at 1p; purchasing tickets in advance is recommended.

  • 🎧 Gates Open / DJ Dolce Vita at 1p / Elda Berlin at 1:30p / Gabi at 1:45p / The Alpha Gals at 2:45p / Wolftrap at 3:45p / Sunny War at 4:45p / Island Hip Hop at 5:45p / Ali McGuirk at 6:15p / Island Hip Hop at 7:05p / Kate Taylor at 7:15p / Delanie Pickering at 8p

• 🍂 Fall Family Fun Day at PA, 1-4p / More Info
  Community fall celebration with food, games and music, and costumes are welcome.

• 🍺 3rd Annual Oktoberfest — Nomans Style at Nomans, Oak Bluffs, All Day / More Info / (Sun too)
  Two full days of Oktoberfest in the Yard with German food, beer and live music all day. Activities include keg tapping, stein holding, pumpkin bowling, pretzel throwing, a best-dressed competition and more.

• 🌊 Climate Conversation Chilmark: Menemsha’s Working Waterfront at Chilmark Free Public Library, Chilmark, 2-4p / More Info / Free
  Panel discussion exploring Menemsha’s working waterfront, local economy and climate planning. Held in the library’s Community Room with representatives from the Fishermen’s Preservation Trust and Commercial Dock Working Group.

• 🧵 West Tisbury Quilting Circle Show and Reception at West Tisbury Public Library, West Tisbury, 3-4:30p / More Info / Free
  Meet members of the quilting circle and view their biennial show during the opening reception; refreshments will be served. The quilts remain on display in the Community Room throughout October.

• 🕯️ Community Remembrance Event at Joseph Sylvia State Beach, Edgartown, 5:30-6:30p / More Info / Free
  Sunset gathering hosted by Hospice & Palliative Care of MV to remember loved ones who have died. Meet between the two bridges at the Camp Jabberwocky parking area; the gathering is open to everyone, regardless of hospice affiliation.

Sunday October 4, 2026

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free

• 🏃 Gay Head Run for the Light 10K at Gay Head Lighthouse, Aquinnah, 10a-12p / More Info + Registration / $43.40 incl. fee

• 🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free

Read more

⏱️ This Week on MVacay

We hit the point of 10+ restaurants closed for the season, so I officially published my list of what’s open & what’s closed! I’ll update it about once a week with temporary, seasonal and permanent closures. It also lists what’s OPEN by town, so bookmark it now for the next time you’re wondering where you can go to eat!

🗺️ What To Do This Weekend

Friday, September 25, 2026

• 🎣 Martha's Vineyard Striped Bass and Bluefish Derby @ Derby Headquarters, Dock Street, Edgartown, Daily weigh-ins 8-10a & 7-9p / More Info All Weekend

• 🎨 Bass in the Grass @ The Carnegie, Edgartown, All Weekend / More Info / Free

• 🎬 29th Annual Manhattan Short Film Festival @ MV Film Center, Vineyard Haven, All Weekend / Fri & Sat 7:30p; Sun 4p / More Info

• 📚 Ripple Effects: Short Story Writing Insights with Author Lesley O’Connell @ Vineyard Haven Public Library, 4-5p / More Info / Free
  O’Connell joins writers Elizabeth Shick and Brenda Horrigan for a conversation about short fiction, publishing and her new book.

• 🎣 Fly Fishing Film Tour and Sage Fly Rods Demo @ Kismet Outfitters, / More Info / $20

• 🎬 Gatherings: A Short, A Feature and Line Dancing! @ Grange Hall, West Tisbury, 7p / More Info / Pay what you can
  The screening pairs a dance short with a feature documentary about community, identity and nightlife. Stick around afterward for a downstairs line-dancing class led by Jill Gross.

Saturday September 26, 2026

• 🎬 A Dance Film Workshop @ The Yard, Chilmark, 9a / More Info / Free

• 🎨 Children’s Saturday Crafting with Helen Hall @ Featherstone Center for the Arts, Oak Bluffs, 10a-12p / More Info / $40 register in advance

• 🍻 Oktoberfest Weekend @ Nomans, Oak Bluffs, 11a-9p (Sun too) / More Info
  Expect German-inspired food, beer, live music and playful competitions throughout the weekend. Saturday includes DJ Rockwell from 1-5p, keg toss at 3p, pretzel toss at 4:30p and stein holding at 6p.

• ✂️ Drop-In Crafts: Bookmarks and Key Chains @ Aquinnah Public Library, 12-3p / More Info
  Stop in anytime during the afternoon to make bookmarks and key chains, with additional craft supplies available. Activities are geared toward ages 4+, but children of all ages are welcome.

• 🪶 Nôepe: A Wôpanâak History of the Island @ Aquinnah Town Hall, 2-4p / More Info / Free / Register online
  Brad Lopes of the Aquinnah Cultural Center draws from oral traditions and historical sources to explore Wampanoag history, land and the Island’s landscapes.

• 💃 Fourth Saturday Dance with the MV Ballroom Group @ Stillpoint, West Tisbury, 7-8:30p / More Info / $5-$30
  The evening starts with a short lesson followed by partner, line and social dancing with music from DJ Keren Tonnesen and friends. All ages and experience levels are welcome; come with or without a partner.

Sunday September 27, 2026

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free

• 🧘 Meditation @ Bodhi Path Buddhist Center, West Tisbury, 10-11a / More Info

• 🧘 Softening Into Stillness @ Stillpoint, West Tisbury, 11a-12p / More Info / $30
  This guided practice focuses on embodied awareness, releasing habitual tension and cultivating grounded presence.

• 🎶 The Great American Songbook: May Oskan and Jeremy Berlin in Concert @ Stillpoint, West Tisbury, 4-5p / More Info / $20-$50
  Vocalist May Oskan and pianist Jeremy Berlin interpret classic standards with an emphasis on improvisation and musical interplay.

• 🎬 Elie Wiesel: Soul on Fire @ MV Film Center, Vineyard Haven, 7:30p / More Info / $12

• 🎨 Vineyard Artisans Festivals @ Grange Hall, West Tisbury, 10a-2p / More Info / Free - FINAL OF THE SEASON

• 🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free

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⏱️ This Week on MVacay

I wrote out my annual fall list of favorite traditions and new additions for 2026:

It’s Derby Time, so I wanted to bring out my beginners guide to fishing on MV, and also in honor of the Shenandoah I found my sailing guide as well!

🗺️ What To Do This Weekend

Friday, September 18, 2026

• 🎨 Art Show and Sale to Support Habitat for Humanity @ Grange Hall, West Tisbury, 10a-6p (Sat too) / More Info / Free
  Shop work by Island artists alongside secondhand art and a silent auction. Proceeds support Habitat for Humanity MV while also highlighting local artists.

• ⛵ Shenandoah Parade of Sail @ Tashmoo Cove, Vineyard Haven, 12p / More Info / Free
  Accompany the schooner Shenandoah as she leaves Tashmoo Cove on her final voyage. The sail kicks off a three-day community celebration marking the historic vessel’s return home.

• 🌱 The Giving Garden: Fall Tour, Taste, and Take-Home with Roxanne Kapitan @ MV Public Charter School, West Tisbury, 4-5:30p / More Info / Free
  Tour the school’s food forest and learn about perennial edibles and the basics of forest gardening. Participants can taste plants including pilgrim cranberries and sea kale and take home seeds or plant divisions for their own gardens.

• 🖼️ Opening Reception: The Two Worlds of Denys Wortman @ Martha’s Vineyard Museum, Vineyard Haven, 5:30-7p / More Info / $20

• 🎶 Behind the Curtain With the Nashville Hit Makers @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$103.22
  Nashville songwriters CJ Solar, Phil Barton, Joe Fox and Johnny Clawson perform songs they wrote for major country artists and share the stories behind them. Their credits include music recorded by Morgan Wallen, Blake Shelton, Kenny Chesney, Jason Aldean and others.

• 🎭 Driver’s Seat: Obsessive Compulsive Disaster @ MV Playhouse, Vineyard Haven, 7p (Sat too) / More Info / Pay-What-You-Can
  Written and performed by Ellie Brelis and directed by Leif Moore, this acclaimed solo show traces OCD, a breakup, hospitalization, coming out and recovery with dark humor and candor. The play was written during Brelis’s own 2020 mental health crisis and later performed at the Edinburgh Fringe Festival.

• 🎬 Tony @ MV Film Center, Vineyard Haven, 7:30p (Sat 7:30p + Sun 4p) / More Info / $12

Saturday September 19, 2026

• 🌅 Darkness into Vineyard Light Suicide Prevention and Awareness Walk @ Bend in the Road, State Beach, Edgartown, 5-7a / More Info / $25
  Participants gather before sunrise and walk through daybreak, symbolizing a passage from the darkness of depression and mental illness into hope and healing. Organizers say this will be the final edition of the annual event.

• 🎉 Tivoli Day @ Circuit Avenue, Oak Bluffs, 10a-6p / More Info
  Circuit Avenue turns into a daylong street celebration with food, local artists, shopping specials and family-friendly fun. Live music runs 12-6p at the Main Stage in front of Rockland Trust, Healy Square and The Ritz; rain date is Sunday, Sept. 20.

• 🏃 24th Annual NAACP George V. Tankard Jr. Memorial 5K Road Race/Walk @ Summercamp Hotel + Ocean Park, Oak Bluffs, 9a-12p / More Info

• ⛵ Community Potluck Celebration of Shenandoah @ Black Dog Wharf, Vineyard Haven, 5-7p / More Info / Free

• 🎤 An Evening With Music City’s Rising Stars @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$135.23

Sunday September 20, 2026

• Yom Kippur at Martha’s Vineyard Hebrew Center

• 🎣 Kid’s Mini Derby @ Steamship Authority Wharf, Oak Bluffs, 6-8a / More Info / Free
  A special early-morning fishing event for kids ages 4-14, with prizes and no registration or Derby button required.

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / More Info / Free

• 🎨 Vineyard Artisans Festivals @ Grange Hall, West Tisbury, 10a-2p / More Info / Free

• ⛵ Shenandoah Open Boat Tours @ Black Dog Wharf, Vineyard Haven, 11a-5p / More Info / Free

• 🏈 Football and Yard Games @ Nomans, Oak Bluffs, 1-5p / More Info /

• 🎶 Community Sing @ Tisbury Amphitheater, Vineyard Haven, 5-6p / More Info / Free

• 🎵 Sundays In The Park Concerts @ Ocean Park, Oak Bluffs, 5-7p / More Info / Free

• 🎸 Behind The Curtain: Sunday Edition with The Nashville Hit Makers @ The Strand Theatre, Oak Bluffs, 7-10p / More Info / $23.18-$391.33

Read more

🗺️ What To Do This Weekend

Friday, September 11, 2026

• 🌽 Morning Glory Farm Corn Shuck n Shimmy End-of-Summer Celebration at Morning Glory Farm, 5-8p / More Info
  Live music, grilled corn, farm-fresh food and a corn-shucking competition mark the transition from summer to fall.

• ✡️ Rosh Hashanah Service at The Tabernacle, 5:30p / More Info
  Gather for an evening Rosh Hashanah service; advance registration.

• 🏈 MV Football v Mashpee — Home Opener! at MVRHS, 6p / More Info / Free, donations welcome

• 🎶 Meredith Sheldon “Once We Were Dust” Record Release Show at Martha’s Vineyard Playhouse, 7p / More Info / $35

Saturday September 12, 2026

• 🏃 Run for Hope 5K at Martha’s Vineyard Regional High School, 8a-12p / More Info / $35
  Run or walk this community 5K benefiting social and humanitarian projects supported by the Millers Foundation.

• 🛍️ Chilmark Flea Market at Flea Market Field, 9a-2p / More Info / Last of the Season

• 🥕 West Tisbury Farmers Market @ Agricultural Hall, West Tisbury, 9a-12p / More Info

• ✡️ Rosh Hashanah Service at The Tabernacle, 9:30a/10a / More Info

• 🐐 Barnyard Buddies at The FARM Institute, 9:30-10:30a / More Info / $25 per pair
  Young children and their caregivers can meet farm animals, collect eggs, feed goats and help care for the Friendship Garden.

• 📚 Vineyard Vanguards with Tom Dresser at Oak Bluffs Public Library, 11:30a-12:30p / More Info
  Author Tom Dresser discusses the Vineyarders whose lives and contributions helped shape the Island’s history and culture.

• 🪶 Wampanoag Tribe of Gay Head (Aquinnah) Powwow 2026 at Aquinnah Circle, (Sun too) / More Info / $10 adults per day; $5 ages 5-17, elders & veterans per day
  Celebrate Wampanoag culture and community through traditional song, dance, drumming, food, storytelling and shared traditions.

• 🕯️ Children’s Memorial Ceremony of Remembrance at Edgartown Lighthouse, 1p / More Info
  The annual ceremony gathers families and community members at the lighthouse to remember children whose names are part of the memorial.

• 💜 Recovery Day at The Red House Peer Recovery Support Center, 2-6p / More Info / Free
  Join The Red House for a community celebration recognizing Recovery Month and the strength of recovery.

Sunday September 13, 2026

• 🎣 MV Striped Bass and Bluefish Derby Begins, daily weigh-ins 8-10a & 7-9p / More Info
  The legendary annual fishing competition brings anglers together for great fishing, Island tradition and scholarship fundraising.

• ✡️ Rosh Hashanah Service & Holiday Lunch at Martha’s Vineyard Hebrew Center, 9:30a / More Info

• 🍔 Burgers & Bubbles at Daniel Fisher House, 2-4p / More Info / $162
  Sample burgers from competing Island chefs alongside Champagne, beer and local oysters while voting for the People’s Choice winner.

• 📷 New Photographs — Ray Ewing at The Workshop Gallery, 3-9p / More Info /
  See a presentation of new photographic work by Workshop Gallery member and MV photographer Ray Ewing.

• 🏺 Potter’s Bowl at Featherstone Center for the Arts, 4p / More Info
  Choose a handmade bowl created by local potters and enjoy soup from Island restaurants and caterers at this annual fundraiser.

• 🎬 MV International Film Festival Closing Night: The Siege of Paradise + Closing Night Party at MV Film Center & The Wave MV, 4:30p / More Info /
  The festival closes with the Italian documentary The Siege of Paradise, followed at 6:15p by food, drinks, live music and dancing at The Wave MV.

Read more

⏱️ This Week on MVacay

We’re on the other end of shoulder season now! Here’s the trip itinerary I shared earlier this year if you’re planning a group trip for September/October:

Speaking of quieter season activities, reviving this hiking guide I wrote this time last year:

🗺️ What To Do This Weekend

Friday, September 4, 2026

• 🎨 Annual Vineyard Artisans Labor Day Festival @ Agricultural Hall, West Tisbury, Fri 4:30-6:30p; Sat-Sun 10a-4p / More Info
  The Island’s largest art show features only Island artists, with furniture, clothing, ceramics, jewelry, fine art, artist demonstrations, and local music.

• 🎷 MV Jazz and Blues Summerfest @ Union Chapel & Strand Theatre, Oak Bluffs, Fri 6-9p; Sat 6-9p; Sun 5-9p / More Info / $50 and up
  Friday features Endea Owens and Dominique Smith at Union Chapel; Saturday brings The Huntertones and Uptown Royalty NYC to Union Chapel. Sunday’s finale moves to the Strand Theatre with The String Queens, Sammulous, and Affiniti NYC.

• 🎨 First Friday Vineyard Haven @ downtown Vineyard Haven & Owen Park, 10a-11p / More Info / Free
  A full day of art, music, food, shopping, and community events spans downtown.

  • 10a-2p: Daytime Art Market at Beach St. Extension, plus an Art Hang at Althea Designs.

  • 12-9p: Live music throughout downtown and Owen Park featuring Beach Plum Jam, Tobey Sol LaRoche, Sparkestra, The Lunarchs, David Mintz, The Roundabouts, and JakeBuddy Band.

  • 5p-dusk: Food trucks, local artists, vendors, nonprofits, and a free art activity at Owen Park.

  • 9-11p: Silent DJ Party at Owen Park Beach with PathwaysARTS.

• 🎣 Family Fishing — OB Fishing Pier @ Oak Bluffs Fishing Pier, 9:30-11:30a / More Info

• 🫧 Bubbles and Beyond: Outdoor Sensory Play @ Edgartown Public Library, 10:30a-12:30p / More Info

• 🦞 Grace Church Lobster Roll Fundraiser @ Grace Episcopal Church, 3-6p / More Info / Last Chance!

• 🎶 Sunset Concert Series — Johnny Hoy and the Bluefish @ MVCMA Tabernacle, 6-7:30p / More Info / Free-will offering

Saturday, September 5, 2026

• 🎣 MVSA Used Tackle Sale @ MVRHS Parking Lot, Oak Bluffs, 8a-1p / More Info
  Shop used shore and boating gear including rods, reels, lures, tackle, life jackets, kayaks, canoes, and more. Proceeds benefit MVRHS scholarships and MV veterans; cash, Island checks, and Venmo are accepted.

• 🏃 Foot It for Felix 5K @ Felix Neck Wildlife Sanctuary, Edgartown, 8:45-11a / More Info / $32.80; Kids’ Fun Run free
  The Kids’ Fun Run/Walk begins at 8:45a, followed by the 5K at 9a along Felix Neck’s pine-needle trails and pond views. 5K registration closes Sept. 4 at 12:01p; Kids’ Fun Run registration closes Sept. 3 at 12:01p.

• 🥕 West Tisbury Farmers Market @ Agricultural Hall, West Tisbury, 9a-12p / More Info

• 🛍️ Chilmark Flea Market @ Flea Market Field, Chilmark, 9a-2p / More Info /

• 🐐 Goat Yoga MV @ Native Earth Teaching Farm, Chilmark, 11a-12p / More Info / $30

• 🪁 Martha’s Vineyard Wind Festival @ Waban/Alley Park, Oak Bluffs, 11a-dusk / More Info / Free
  Kite-making runs from 11a-1p, followed by youth and adult flying competitions, prizes, and community kite flying through dusk. The day also includes frisbee games, food, DJ music, bubbles, and other activities; rain date is Sunday, Sept. 6.

• 🎶 Live Music: Chris Knott & Mixt @ West Tisbury Public Library, 2:30-4p / More Info / Free

Sunday, September 6, 2026

• 🏃 The Inkwell Mile Community Run @ Nomans, 15 Island Inn Road, Oak Bluffs, meet 8a; run/walk 8:30a / More Info / Free
  More Than A Mile presents a community run and walk, with participants meeting at Nomans at 8a before moving at 8:30a. Registration is available online.

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p

• 🥁 Weekly Museum Open House and Family Samba @ Milokan Cultural Center and Drum Museum, Chilmark, 3-6p / More Info / $15 individual

• 🎶 Sundays in the Park Concert @ Ocean Park, Oak Bluffs, 5:30-7:30p / Free

Monday, September 7, 2026

• Labor Day

• Brazilian Independence Day

• 🌱 Beetlebung Farm Tour @ Beetlebung Farm, Chilmark, 4-4:30p / More Info / $5

• 🌿 Garden Tasting Tour @ The Farm Institute, 5-6:30p / More Info

Read more

⏱️ This Week on MVacay

The people are asking for it! The first batch of 2027 dates are here. I did some historical research to gather a few predicted dates, plus some confirmed/reported 2027 dates:

But if you’re still here, don’t worry, the 2026 dates are kept up-to-date both here (updated occasionally) and updated weekly behind the paywall:

🗺️ What To Do This Weekend

Friday, August 28, 2026

• 🏃 Obstacle Course @ Oak Bluffs Public Library Lawn, Oak Bluffs, 10-11:30a / More Info / Free

• 🦀 One Bad Crab: Screening, Discussion and Green Crab Tasting @ Vineyard Haven Public Library, Vineyard Haven, 4p / More Info / Free
  Watch the 38-minute environmental film One Bad Crab, then hear from members of the MV shellfish community about the invasive European green crab.

• ⚓ Little Lady Restoration Celebration @ Gannon & Benjamin Marine Railway, Vineyard Haven, 4:30-6:30p / More Info
  Celebrate the history and restoration of the Little Lady, a 1929 wooden fishing vessel that has worked MV waters for generations.

• 🎉 Built on Stilts 30th Anniversary Soirée and FUNdraiser @ Portuguese-American Club, Oak Bluffs, 6-9p / More Info / Sliding scale
  Celebrate 30 years of Built on Stilts with finger food, mingling, pop-up performances, a silent auction, cash bar and dance party, all supporting the organization’s inclusive performing arts programming.

• 🎶 Friday Nights with Johnny Hoy and the Bluefish @ Featherstone Center for the Arts, Oak Bluffs, 6-8p / More Info / $20

• 🎵 Special Performance by Harpist Lexie Lowell @ Stillpoint, West Tisbury, 6-7p / More Info / $20-$40
  NYC-based pop harpist and singer-songwriter Lexie Lowell performs an intimate set paired with light guided breathwork and meditation for a relaxed evening of music.

• 🎶 Sunset Concert Series — Dock Dance Band @ MVCMA Tabernacle, Oak Bluffs, 6-7:30p / More Info / Free-will offering

• 🎭 Women Behaving Badly @ Union Chapel, Oak Bluffs, 7-9p / More Info / $40-$70
  Mezzo-soprano, author and performer Heather Poduska stars in a genre-blending one-woman show combining soaring vocals, sharp humor and storytelling about finding your own voice. Use code MVACAY for a discount!

Saturday, August 29, 2026

• 🥕 West Tisbury Farmers Market @ Grange Hall, West Tisbury, 9a-12p / More Info / Alternate market location today

• 🛍️ Chilmark Flea Market @ Flea Market Field, Chilmark, 9a-2p / More Info

• 🎭 The Fabulists @ Tisbury Amphitheater, Vineyard Haven, 10a

• 🐴 Misty Meadows Saturday Pony Rides @ Misty Meadows Equine Learning Center, West Tisbury, 10a-12p / More Info / $30

• 🎨 Jenn Brown Textile Art + MV Glassworks Collaboration Reception @ The Field Gallery, West Tisbury, 4-6p / More Info /
  See the results of MV Glassworks’ 2026 artist residency with Jenn Brown, whose textile-based ideas have been translated into new glass forms through months of collaboration with the MVG team.

• 🎭 Vineyard Arts Project Open Call Resident Work-in-Progress Sharing @ Vineyard Arts Project, Edgartown, 5-6p / More Info / Pay what you can
  See works in progress from Vineyard Arts Project’s 2026 Open Call residents, selected from more than 350 applicants for a week of free development time on MV. Featured projects include work by Ben Anderson and Justin Craig, Abs Wilson and Veronica Mansour, Fouad Dakwar, and The Pack Theatre Company.

• 🎶 Indigo Girls @ MVCMA Tabernacle, Oak Bluffs, 7:30p / More Info / $71

Sunday, August 30, 2026

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / /

• 🎨 Vineyard Artisans Festival @ Historic Grange Hall, West Tisbury, 10a-2p / More Info

• 🎤 Community Sing @ Tisbury Amphitheater, Vineyard Haven, 5-6p / More Info / Free

• 🚣 38th Annual Oar & Paddle Regatta @ Island Spirit Kayak, State Beach, Oak Bluffs, 9-11a / More Info / $50
  Kayakers, paddleboarders, swimmers and other human-powered watercraft take on a 2.4-mile race on Sengekontacket Pond to raise money for Friends of Sengekontacket. The race itself starts at 10a, with check-in beforehand.

• 🧘 Sound Bath with Anna Marden @ Stillpoint, West Tisbury, 4-5p / More Info / $20-$40

• 🎶 Restorative Sound Journey @ Peaked Hill Studio, Chilmark, 4-5:15p / More Info / $30-$45

• 🎶 Sundays in the Park Concert @ Ocean Park, Oak Bluffs, 5:30-7:30p / Free

Read more

⏱️ This Week on MVacay

My kiddos were finally old enough to go on the pirate ship! I loved adding this to our MV favorites list. It was so interactive! Just a few weeks left to fit it in for the summer:

I’ve been collecting a list of some fascinating facts and put them all together in this fun post. Hopefully even the most veteran Vineyarders learn something new:

🗺️ What To Do This Weekend

Friday, August 21, 2026

• 🕯️ The Open Door Club by SANCTUAIRE @ 15 Church St., Edgartown / All Weekend thru 8/29.
  A fragrance pop-up and historic photo installation highlighting Black leisure communities.

• 🌿 Polly Hill Arboretum Staff-Led Botanical Spotlight Tour @ Polly Hill Arboretum, West Tisbury, 10-11a / More Info / Included with admission

• 🎨 Artist Party @ KIN, 12 N Water St., Edgartown, 3-7p
  Featuring jewelry by Sissy Yates Design, ceramics by Creney Ceramics and paintings by Marston Clough, with snacks and refreshments.

• 🎨 Brush and Blooms — A Flower Painting Workshop with Traeger di Pietro @ Morning Glory Flower Farm, West Tisbury, 3-5p / More Info / $175

• 🎸 Porch Concert: Mike Mok and the Em-Tones @ West Tisbury Public Library, 3:30-4:30p / More Info / Free

• 🧘 Family Yoga @ The Yard, 4-5p / Free

• 🎶 Sunset Concert Series — Jon Bates Band @ MVCMA Tabernacle, Oak Bluffs, 6-7:30p / More Info / Free-will offering

• 😂 15th Annual MV Comedy Fest @ The Strand Theatre, Oak Bluffs, 8p / More Info / $78.25 GA
  Week 3 lineup includes Damon Williams, Brooklyn Mike, Tony Wood and James “Talent” Harris.

  🎆 Oak Bluffs Fireworks Display @ Ocean Park, after 9p / More Info
  Rain date Sat., Aug. 22. Best viewing is from Ocean Park. Blankets may not be left unattended before 4p, and tarps are prohibited. Parking at Washington Park and Alley-Waban Park opens at 3:30p and is $20 cash only. VTA buses will operate at Tuckernuck & Seaview Ave. and Dukes County & New York Ave.; expect road closures, detours and heavy traffic before, during and after the show.

Saturday, August 22, 2026

• 🏃 MV Hospital Sullivan 5K Run/Walk @ Washington Park, Oak Bluffs, 9a / More Info / $32.80
  Scenic East Chop 5K with a Kids Dash, refreshments and awards. Proceeds benefit MV Hospital’s Alpha-gal Syndrome Research & Clinical Program.

• 🥕 West Tisbury Farmers Market @ Grange Hall, West Tisbury, 9a-12p / More Info / Alternate market location today

• 🛍️ Chilmark Flea Market @ Flea Market Field, Chilmark, 9a-2p / More Info

• 🎭 The Fabulists @ Tisbury Amphitheater, Vineyard Haven, 10a /

• 🎷 MV Jazz Experience @ Trinity Park Tabernacle, Oak Bluffs, 1-7p / More Info / $56+
  Featuring Alex Bugnon, Tia Fuller, Michael Mayo, Wycliffe Gordon, Bill Easley, Jimmie Highsmith Jr. and Taryn Sunchild.

• 🛍️ 6th Annual Neighborhood Goods @ 27 Hewing Field, Chilmark, 1-4p
  Sips and shopping with Awet New York, Cesta Collective, Coco’s Kids, Gogo Jewelry, Jahde Leather Atelier, La Ligne, Midnight Farm, Overset and more. Benefits Chilmark Preschool.

• 🎨 Arts District Stroll + Art Yard Sale @ Dukes County Ave., Oak Bluffs, 4-7p / More Info / Free
  Visit Alison Shaw Gallery, Michael Blanchard Studio and Judith Drew Schubert Studio, plus Galaxy Arts MV’s Art Yard Sale in the corral at 88 Dukes County Ave.

• 💃 Kiki Artist Collective: How Far Can We Go @ Vineyard Arts Project, Edgartown, 5-6p / More Info / Pay what you can
  Work-in-progress movement performance rooted in ballroom culture.

• 🎬 American Diner: Teaser Screening and Conversation @ Stillpoint, West Tisbury, 6-9p / More Info / Free, RSVP, donations encouraged
  Includes a 10-minute documentary preview (a docuseries collaboration between Artcliff Diner chef Gina Stanley and filmmakers Ian Moubayed, director of Keys to the City and Helen Cho) filmmaker conversation, then dinner, drinks and music.

• 🎤 Combat to Comfort @ Owen Park, Vineyard Haven, 7-8p / More Info / Free
  Interview and open Q&A with Navy veteran and humanitarian Dr. Rev. William Devlin about his work in conflict zones around the world.

• 😂 Seth Meyers Live: A Benefit for Chilmark Preschool @ MV Performing Arts Center, Oak Bluffs, 7:30p / More Info / $161.90

Sunday, August 23, 2026

• ⛪ The Very Rev. John Streit, Preacher and Celebrant @ Trinity Episcopal Church on Ocean Park, Oak Bluffs, 9-10a / More Info / Offering

• 🏀 Chappy’s Play It Forward Sports Equipment Giveaway @ Steere the Course Mini Golf, Vineyard Haven, 10a-12p / More Info / Free
  Free golf, tennis, baseball, hockey gear, cleats, bikes and more for Island kids and families. Non-perishable food donations for the Island Food Pantry are welcome.

• 🛍️ Oak Bluffs Open Market @ Washington Park, Oak Bluffs, 10a-2p / /

• 🎨 Vineyard Artisans Festival @ Historic Grange Hall, West Tisbury, 10a-2p / More Info

• 🎤 Community Sing @ Tisbury Amphitheater, Vineyard Haven, 5-6p / More Info / Free

• 🦈 From Jaws to Awe: How the World Moved from Fear to Fascination @ MV Museum, Vineyard Haven, 5-6p / More Info / $15-$25

• 🎶 Sundays in the Park Concert @ Ocean Park, Oak Bluffs, 5:30-7:30p / Free

Read more

⏱️ This Week on MVacay

I’ve seen a lot of local chatter about off-island organizations hosting local pop-ups. In this article I shared how you can bring something to Martha’s Vineyard while ALSO supporting the people, businesses and organizations that work so hard year round to make this such a special place to visit:

🗺️ What To Do This Weekend

Friday, August 14, 2026

• 🎡 164th Annual Agricultural Fair at MV Agricultural Hall, 10a–11p Fri & Sat; 10a–6p Sun / $10-$15 / Tickets / Fiesta Rides / + $10 Cash for Parking

  A classic MV summer tradition, the Ag Fair brings together carnival rides, animals, exhibits, competitions, food and family activities.

  • Friday highlights: Kids Corn Husking Competition at 2p, Chopstick Knitting Competition at 3p and Pet Show at 3p.

  • Saturday highlights: Kiddie Pedal Tractor Pull at 11a, Shucking Competition at 3p, Sack Races at 5p and Tug-O-War at 5:30p.

  • Sunday highlights: Dog Show at 10a, Chopstick Knitting Competition at 3p and Women’s Skillet Toss at 3p.

  • Rides are separate from admission and parking: Unlimited ride megapasses are $70 per person per day; Friday-night unlimited wristbands are $50 from 5–10p. Individual ride cards are also available at carnival kiosks.

• 🎬 MVAAFF (Sat too) / $30-60 per individual program

  The Martha’s Vineyard African American Film Festival continues its weekend programming with screenings and conversations featuring filmmakers, actors and entertainment-industry leaders. A few films with tickets remaining:

  • 1–2:45p — The Color of Cola: A 79-minute screening followed by a conversation with co-directors Stanley Nelson and Jacqueline Olive, moderated by Warner Bros. Discovery EVP Sheereen Miller-Russell.

• 👗 The Co-Ops Summer Pop-Up at Salte, 12–4p / More Info

• 🤖 2026 Black Education Forum at Old Whaling Church, 4–5:30p / More Info / Free / Registration is required.

• 🧘 Free Family Yoga at The Yard, 4–5p / Free

• 🎹 Sublime Schubert at Stillpoint, 5p / More Info / $20

• 🎶 Sunset Concert Series – The Roundabouts at MVCMA Tabernacle, 6–7:30p / Free-will offering

• 🎭 Hadestown: The Musical at MV Film Center, 7:30p / More Info / $18

• 💃 Built on Stilts at Union Chapel, 7:45–9p (Sat, Sun + Mon too) / More Info / Free

  The Island’s Community Dance and Performance Festival celebrates its 30th year with free, inspired dance and other forms of performance.

Saturday, August 15, 2026

• 🏖️ Greek Week on MV at Inkwell Beach, All Day (Sun too) / Free

• 🥕 West Tisbury Farmers Market at GRANGE, 9a-12p / More Info (note: alternate location thru 8/22)

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info

• 🏃 5K Run for Camp Jabberwocky at The FARM Institute, 9a / More Info

• 🎭 The Fabulists at Tisbury Amphitheater, 10a

• 🎉 MV Vibe Fest at Alley/Waban Park, 11a–8p / More Info / Free

  Vibe Fest brings food, music, culture and community together for a full day in Oak Bluffs, with local vendors, performers and organizations gathering near Inkwell Beach. It includes a Vibe Fest Meets Greek Fest, a Truth & Joy Celebration with performances and a community parade with the MV Diversity Coalition. Features a Silent Disco with HBCU Legacy Week, Food including Everybody Gotta Eat, Eleven Circuit, Honorary Tavern and Yommi.

• 🎬 MVAAFF (Fri too) / $30-60 per individual program

  • 2–3p — Warner Bros. Television Group Celebrates the Stars Behind Hit TV Shows: Featuring actors Luke Tennie, Nicholas Duvernay and Bre-Z, with Extra senior correspondent Mona Kosar Abdi moderating.

  • 7–10:30p — Advanced Screening: Lanterns Ep. 1 + Earth, Wind & Fire: An advance screening of Lanterns Episode 1 followed by Earth, Wind & Fire (To Be Celestial vs. That’s the Weight of the World) and a conversation with Questlove, moderated by Sheereen Miller-Russell.

• 🎤 Vineyard Sound Farewell to Summer Show at Old Whaling Church, 7–9p / More Info

• 🎸 MVCMA Benefit Concert: The Wallflowers at MVCMA Tabernacle, 7:30–11p / More Info / $86+

• 🌙 MV Soulfest Kickoff Party – Vineyard Speakeasy: R&B After Dark at Indigo, 10p–12:45a / More Info

  MV Soulfest kicks off its 5th anniversary celebration with a late-night R&B party at Indigo in Edgartown. Expect special guest DJs, cocktails, food.

*As a reminder, sold out events are excluded from MVacay listings.

Sunday, August 16, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• ☀️ MV Soulfest Sunday Soulfest Day Party at Eleven Circuit, 3–8p / More Info

• 🎻 Atlantic Harmony String Duo at MV Film Center, 4–5p / More Info / $25

• 🎻 Harlem Quartet at Old Whaling Church, 5–6:30p / More Info / $40

• 📖 Author Talk: Eugene Robinson — Freedom Won, Freedom Lost at Chilmark Community Center, 7–8:30p / More Info / $75

• ✨ Magic and Mentalism at Portuguese-American Club, 8–9:30p / More Info / $35

• 🎤 Community Sing at Tisbury Amphitheater, 5-6p / More Info / Free

• 🎶 Sundays in the Park Concert at Ocean Park, 5:30-7:30p / Free

Read more

⏱️ This Week on MVacay

With so many Black, HBCU, Greek, and African American events happening this week, I wanted to resurface one of my favorite guides, which I’ve updated to include businesses that are new for 2026:

My paid subscribers have a special perk this week: two handy pocket guides! They take the 100-page, not-so-mobile-friendly event guides and distill them into easy-to-skim resources to help you plan your time at both events:

Subscribe now

🗺️ What To Do This Weekend

All Weekend

• 💃 Built on Stilts at Union Chapel, 7:45-9p nightly / More Info / Free
  The community dance and performance festival celebrates its 30th year with performances Friday, Saturday, and Sunday from 7:45-9p each night.

• 🎬 MV African American Film Festival at MVPAC, times vary / More Info
  The annual festival presents film screenings, conversations, and cultural programming across MV from Aug. 7-15. Individual tickets available.

• Massachusetts Tax-Free Weekend

Please note that MVacay’s Weekend Updates exclude SOLD OUT Events!

Friday, August 7, 2026

• 🎣 Family Fishing at Oak Bluffs Fishing Pier, 9:30-11:30a / More Info /
  Kids, teens, and their adults can fish with an Oak Bluffs librarian, with equipment and supplies provided.

• 🎉 First Friday Vineyard Haven throughout downtown Vineyard Haven, 10a-11p / More Info / Free

  • 10a–2p: Daytime Art Market + Art Hang (Live Music at 12)

  • 4p: Live Music Begins

  • 5p: Food trucks open, activities on the hill (Owen Park)

  • 7:30–8p: Fire performance

  • 9–11p: Silent DJ Party

• 🌻 Pick Your Own Sunflowers at The FARM Institute, 10a-3:30p (Sat too) / $25

• 🗼 National Lighthouse Day at Gay Head Lighthouse, 10a-4p

• 🎨 Art En Blanc at Cottagers, Inc., 10a-8p (Sat too) / Free
  Explore a curated exhibition of paintings, sculptures, graphics, and quilts by prominent Black artists.

• 🛍️ Sips & Sweets with She Shell Designs at Rainy Day, Vineyard Haven, 12-4p

• 💬 Center for Constitutional Rights: A Conversation with Vince Warren at Oak Bluffs Public Library, 3-5p / More Info

• 🧘 Family Yoga at The Yard, 4-5p / More Info / Free

• 🎶 Sunset Concert Series with Anna Laura Quinn at Trinity Park Tabernacle, 6-7:30p / More Info / Free-will offering

• 🎭 As You Like It at Tisbury Amphitheater, 6p (Sat too) / More Info

• 🎷 Grace Kelly Benefit Concert at Old Whaling Church, 7:30-9:30p / More Info / $30-$100
  Saxophonist, vocalist, and composer Grace Kelly celebrates more than 20 years of music while raising funds for Island nonprofits.

• 🎸 Will Dailey in Chilmark at Ocean View Farm Road, 7:30-9p / More Info / $40

• 😂 15th Annual MV Comedy Fest at The Strand Theatre, 8-10p / More Info / $72+
  The annual comedy festival returns to the Strand Theatre for an evening of live stand-up.

• 🎵 BlueSwitch Blues Band at Portuguese-American Club, 8-10p / $10 at door

Saturday, August 8, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info

• 🎭 The Fabulists at Tisbury Amphitheater, 10a / More Info

• 🌊 August Seine Net Event at Doug’s Cove Preserve, 12-2p / More Info / Free
  Join local scientists as they drag a seine net through the pond and identify the coastal species collected.

• 👜 Create Your Legacy: Bee Blunt x Tote-Ally Yours Pop-Up at Tote-Ally Yours, Oak Bluffs, 6p / More Info

• 🎤 A Soulful Evening with Theresa Thomason at Stillpoint, 7p / More Info / $30-$60

• 😂 Comedian Jackie Flynn Live Stand-Up Comedy Event at MV Film Center, 7:30p / More Info / $30-$35

Sunday, August 9, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🏀 Alex Cohen Memorial Basketball Marathon at Chilmark Community Center Basketball Court, 10:30a-3:30p / More Info / $30 solo; $75 per team of three

• 🙏 Festival of Worship in Word and Song at Trinity Park Tabernacle, 2p / More Info / Donations welcome
  Rev. Senator Raphael G. Warnock and music director Mark A. Miller lead an afternoon of worship, music, and community.

• 🎨 Anonymous Art at Featherstone Center for the Arts, Art Barn, 4p / More Info / $30
  Guests can compete for anonymous 6-by-6-inch artworks while enjoying wine, beer, and appetizers.

• 🎤 Community Sing at Tisbury Amphitheater, 5-6p / More Info / Free

• 🎶 Sundays in the Park Concert at Ocean Park, 5:30-7:30p / Free

BONUS SECTION: I usually don’t talk about Weekday Fun…but if there’s ever a week to do it it’s this week! I didn’t audit which of the following is sold out, but get out there and enjoy! Upgrade to Paid to get the rest of August.

Monday, August 10, 2026

• Motown Monday at MVCMA Tabernacle, 6–7p / Broadway Divas at Martha’s Vineyard Film Center / Black Oak Ensemble at First Congregational Church of West Tisbury / Magic and Mentalism with Magic Mike Jacobson at Chilmark Community Center / Otra at Grange Hall, 5p / Bob and David Climb Machu Picchu at Grange Hall, 7:30p

Tuesday, August 11, 2026

• The Vineyard Classic 5k at Washington Park /Martha’s Vineyard HBCU College Fair at Trinity Park Tabernacle / The Pursuit of Home: An Evening on Martha’s Vineyard / Martha’s Vineyard Soulfest Opening Night Party at 11 Circuit Avenue / Silo Session with Shawan Rice at Slough Farm / Martha’s Vineyard Black History & Legacy Tour Experience from Union Chapel / Tuesday Blues with Jeremy Berlin + Delanie Pickering at Morning Glory Farm

Wednesday, August 12, 2026

• Black Wealth Weekend Begins / Rotational Grazing Tasting Tour at Beetlebung Farm / A Conversation with Belle Burden & Amy Schumer at The Yard / Terrible Thicket Escape Room at Vineyard Haven Public Library, 3:30p + 5p / This Is Our Island at MV Film Center / Skippy Scallop Storytime and Touch Tank at Grange Hall /

Thursday, August 13, 2026

• August 13 - The Momentum Summit / Sen. Raphael Warnock at the Chilmark Community Center / Summer Institute: Meet the Puzzlers at Martha’s Vineyard Hebrew Center / Martha’s Vineyard Agricultural Fair Begins / Fairy Houses and Gnome Homes in the Sunflower Field at The FARM Institute

Read more

⏱️ This Week on MVacay

This week I talked about my first Inter-Island Day trip to Nantucket. It was so easy! I asked Hy-Line Cruises for a discount code, and they said you can use MVACAY for 20% inter-island travel through the rest of 2026. Enjoy! 🫡

I recently saw someone ask the question “What’s the MV equivalent of WholeFoods?” And the answer was FARM STANDS! I aggregated my favorite resources for eating local and supporting farms on MV ❤️

This old post of mine includes all my favorite traffic and parking hacks and ways to stay out of town in August:

🗺️ What To Do This Weekend

All Weekend

• 📚 Annual Friends of the West Tisbury Library Book Sale at West Tisbury School, West Tisbury, 9a-3p / More Info / Free (half-price books Sunday).

• 🎓 HBCU Legacy Week on the Vineyard Celebrates 10 Years / More Info

• 🎨 Art En Blanc on the Vineyard at The Cottagers, Inc., Oak Bluffs, 10a-8p / More Info / Free

• 📖 Sankofa 2026 at Oak Bluffs Public Library, 10a-4:30p / More Info / (Sat too)

• 🎨 HBCU Arts Festival at Various locations, Various times / More Info (Sat+Sun)

Friday, July 31, 2026

• 🎬 MV Documentary Week at MV Film Society venues, last day / More Info

• 🎓 The Blueprint for HBCU Sustainability, Part II: Strategic Backing and Community Empowerment at Oak Bluffs Public Library, Oak Bluffs, 10-11a / More Info / Registration recommended

• 🎶 Australian Musician Bobby Alu Live at Behind the Bookstore, Edgartown, 11a-12p / More Info

• 🌅 Sunset Concert Series: The Dukes of Circuit Avenue at Trinity Park Tabernacle, Oak Bluffs, 6-7:30p / More Info / Free-will offering

• 🎨 Island Visions: Art Showcase + Marketplace at The Strand Theatre, Oak Bluffs, 6-10:30p / More Info / $25
  Live performances, vendors, music and panel conversations in support of a local community member recently released from ICE detention.

• 🎼 Concert Celebrating Joy, Justice and Resilience at Old Whaling Church, Edgartown, 7:30-9p / More Info / $20 suggested
  Composer Mark Miller and singer Julian Wamble will perform original art songs featuring Black poets.

Saturday, August 1, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info

• 🚙 Vineyard Series Vintage Land Rover Show at Nomans, Oak Bluffs, 9-11a / More Info
  The show features more than 70 vintage Land Rovers from around the country, plus breakfast and live music.

• 🛍️ Annual MVCMA Craft and Artisan Fair at MVCMA Tabernacle, Oak Bluffs, 9a-2p / More Info / Free
  The rain-or-shine fair features handmade art, jewelry, pottery, textiles, food products and other goods from new and returning vendors.

• 🎨 Artists’ Premiere: Jennifer Christy & Jhenn Watts at Field Gallery, West Tisbury, 4-6p / More Info

• 🎭 Serendipity: The Musical at Vineyard Arts Project, Edgartown, 5-6p / More Info / Pay what you can

• 📷 Matt Cosby Greatest Hits Photo Show at The Workshop Gallery, Vineyard Haven, 5-7p / More Info

• ⚾ MV Sharks vs. TBA at Shark Tank at MVRHS, Oak Bluffs, 6:35p / More Info

Sunday, August 2, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 👩🏾 The Black Moms Fair at Chilmark Community Center, Chilmark, 12-4p / More Info / $149

• 🌱 Slough Farm Tour at Slough Farm, Edgartown, 12:30-1:30p / More Info / Registration required

• 💐 Family Flower You Pick at Slough Farm, Edgartown, 4-6p / More Info / Registration required; Sundays through Aug. 30

• 📚 Author Talk: Maggie Haberman — Regime Change at MV Performing Arts Center, Oak Bluffs, 7-8:30p / More Info / $95

• 🎬 Harvest Film + Live Discussion at MV Film Center, 7:30p / More Info / Tickets required

• 🎤 Community Sing at Tisbury Amphitheater, 5-6p / More Info / Free

• 🎶 Sundays in the Park Concert at Ocean Park, 5:30-7:30p / Free

Read more

⏱️ This Week on MVacay

The Dining Guide is updated for 2026 (I hope you don’t look too closely, I swapped some out) You’ll never hear me give a bad review, but lots of positive personal experiences. More recent faves behind the paywall below today too.

🗺️ What To Do This Weekend

Friday, July 24, 2026

• 🛍️ Roller Rabbit Pop-Up at The Shop by WHEAT, 9a-5p thru Sun / More Info
  Shop Roller Rabbit’s limited-edition Monkey on the Vineyard collection and new summer arrivals. Friday and Sunday include beverages from Wheat Store Cafe and treats from The Sweetish Fish, while Saturday features Mad Martha’s ice cream.

• 📚 Library Friends of Oak Bluffs Book Sale at Oak Bluffs Public Library, 10a-4p / More Info / (Sat too)

• 🦪 Chilmark Community Trust: Shellfish, Science & Shucking at The Yard, 1-3p / More Info

• 🎬 An Evening with Dawn Porter at MV Museum, 5p / More Info

• 🎶 Sunset Concert Series: Alwyn Robinson at Trinity Park Tabernacle, 6-7:30p / More Info / Free-will offering

• 🎭 An Evening of Magic, Illusion and Mind-Blowing Juggling at MV Film Center, 7p / More Info / $35 front section, $30 main section

• ⚾ Chilmark Resident Appreciation Night: MV Sharks vs. Ocean State Waves at MVRHS Shark Tank, 7:05p / More Info

• 🐉 The Hobbit at Katharine Cornell Theater, 7:30-9p / More Info / $20

Saturday, July 25, 2026

• 🎾 MV Open Tennis Tournament at Farm Neck Tennis and Vineyard Family Tennis, Fri 12-7p, Sat 8a-7:30p, Sun 8a-5p / More Info

• 🏃 Flutie 5K with Island Autism at West Tisbury School, 8:30-11a / More Info

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info

• 📚 Vineyard Haven Library Grand Opening at Vineyard Haven Library, 10a-12p+
  Celebrate the library's newly renovated Main Street building with a ribbon cutting at 10a, a family concert by musician Tom Sieling at 11a, and cake and refreshments beginning at 12p.

• 🎪 Children’s Festival at Trinity Park Tabernacle, 10-11:30a / More Info
  Families can enjoy games, crafts, treats and activities designed especially for children. Game tickets may be purchased and exchanged for reward tickets and prizes.

• 🎠 Flying Horses Carousel 150th Birthday Party at Flying Horses Carousel and Union Chapel, 10a-5p / More Info
  The day includes an airbrush artist, scavenger hunt, DJ entertainment, lawn games, tie-dye demonstration, cornhole challenge, limbo contest and dance party, followed by a 4p birthday singalong. Prize giveaways take place every half hour at the carousel beginning at 10:30a.

• 🎨 Chappy Art Show and Artisan Fair at Chappaquiddick Community Center, 12-4p / More Info
  Meet Chappaquiddick artists and Island artisans during an afternoon fair on the center’s front porch.

• 🎤 Della Hardman Day at Ocean Park, 4-6p / More Info / Free
  Mara Brock Akil joins Dr. Farah Jasmine Griffin for a conversation centered on “Our Stories, Our Legacy,” the free community gathering honors artist, educator and civic leader Dr. Della Hardman.

• 🐾 Celebration of Pets at MV Agricultural Hall, 1-3p / More Info
  Community members are invited to bring pets from both farm and home.

• 📚 Author Talk: Washashores Review, Vol. 2 at Edgartown Public Library, 6-7p / More Info

• 🎶 Vineyard Sound Mid-Summer Show at Old Whaling Church, 7-9p / More Info

• ⚾ MV Sharks vs. North Shore Navigators at MVRHS Shark Tank, 7:05p

• ✨ Light Up the Lagoon at Lagoon Pond, 8:30-9:15p / More Info
  Watch illuminated boats travel from opposite ends of the pond while residents light the shoreline with lanterns and flashlights. Public viewing areas are available on both sides of the lagoon; the rain date is Sunday.

Sunday, July 26, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🥁 Weekly Museum Open House and Family Samba at Milokan Cultural Center and Drum Museum, 3-6p / More Info / $15 individual, $50 family of four or more
  Explore a collection of drums from around the world from 3-5p, followed by a participatory samba session at 5p. All ages and experience levels are welcome, and drums are provided.

• 🧘 Sound Bath with Anna Marden at Stillpoint, 4-5p / More Info / $20-$40 sliding scale

• 🎪 Chilmark Preschool Annual Family Festival at Beetlebung Campus Green, 4-6p / More Info / Free
  Enjoy live music by Wolftrap, Stoney Hill soft serve, glitter tattoos, games, bubbles and make-your-own oyster ornaments. The free community celebration is open to everyone, with an all-day dine-and-shop-to-donate fundraiser at the Chilmark General Store.

• 🎨 RISD Emerging: Recent Alums from Rhode Island School of Design Opening Reception at Featherstone Center for the Arts, 4-6p / Free

• 🎶 Emi Ferguson, Flute & Voice, with Pianist Jacob Rhodebeck at Old Whaling Church, 4-5:30p / More Info / $40

• 🎤 Community Sing at Tisbury Amphitheater, 5-6p / More Info / Free

• 📚 Freedom of Speech: Lee Bollinger and Jelani Cobb at MV Performing Arts Center, 7p / More Info

• 🎶 Potluck Jam 72 at Chilmark Community Center, 7-10p / More Info
  Bring a dish to share and your best energy for an evening of live music and community. The announced lineup includes Ben Taylor, Ryan Montbleau, Isaac Taylor, Lydia Fischer, the Woods School Singers and more.

• 🎶 Sundays in the Park Concert at Ocean Park, 5:30-7:30p / Free

• 🎓 HBCU Legacy Week Begins / More Info

Read more

⏱️ This Week on MVacay

A reminder that if you’re looking for weekday fun, these are a great place to look:

🗺️ What To Do This Weekend

Thursday, July 16, 2026

• [AD] 🏡 The Cottagers, Inc. 39th Annual House Tour at Cottagers’ Corner, 57 Pequot Avenue, Oak Bluffs, 10a-3p / More Info / $85 day of event

  Tour several distinctive Oak Bluffs homes while supporting The Cottagers’ community programs and scholarships.

Friday, July 17, 2026

• 🛍️ Shopbop MV Pop-Up Shop at The Sydney Hotel, 22 Winter Street, Edgartown, 10a-6p daily (Fri-Sun) / More Info

  • Shop brands including PARKE, Flabelus, Hunza G, Hill House Home, FARM Rio, and STAUD in Shopbop’s first MV pop-up.

  • Friday features complimentary PARKE embroidery, Saturday offers Flabelus shoe charm customization, and Sunday includes Hill House Home monogramming.

  • Spend $25+ at any local business during the pop-up and show your receipt to receive a free Shopbop tote, while supplies last. Partnerships with locally owned businesses throughout the weekend.

• 📚 Chilmark Community Trust: Hidden History of MV with Thomas Dresser at The Yard, 1-3p / More Info

• 🎨 Away to See Book Celebration and Summer Raised II Art Exhibition at Eisenhauer Gallery, 5-8p / More Info

• 🌿 Manuel F. Correllus State Forest Bioblitz at Manuel F. Correllus State Forest Headquarters, 5p Friday-5p Saturday (Sat too) / More Info / Free - Register

• 🎶 Sunset Concert Series featuring Phil DaRosa at Trinity Park Tabernacle, 6-7:30p / More Info / Free-will offering

• ⚾ Bollin Trucking and Excavation Night: MV Sharks vs. Ocean State Waves at Shark Tank, MV Regional High School, 7:05p / More Info

Saturday, July 18, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info / Free

• 🏊 Swim Across America — MV Open Water Swim at Menemsha Beach, 8a / More Info / Register to swim

  Swimmers, volunteers, spectators, and supporters will gather to raise funds for cancer programs at Mass General Brigham Cancer Institute at MV Hospital.

• ⛵ Catboats: Sail Sculpin Edgartown 2026 at Old Sculpin Gallery, 10a (Sun too) / More Info

  This multi-day celebration highlights catboats, local artists, maritime history, and special programming at the gallery.

  • 10a: Catboats, Captains, and Coffee

  • 1p: Parade of Sail with entertainment by Outermost Bateria

  • 2p: Mad Martha’s Ice Cream Social

  • 4-6p: Sail Sculpin 2026 Public Reception

• 🪶 19th Annual Native Artisan Market and Festival at Aquinnah Circle, 11a-4p (rain date Sun) / More Info / Free

  Native artists and craftspeople showcase their work alongside live music, food, and dancing. Registration is not required.

• 📷 Simon Gallery in Chilmark off Tabor House Road (follow sign), Chilmark, 11a-3p (Sun too) / More Info / Registration is not required

• 🫐 Berry Festival at First Congregational Church of West Tisbury, 12-4p / More Info

  Berry shortcakes, smoothies, parfaits, pies, lemonade, and raffle items will be available rain or shine.

• 🏺 Pottery and Oysters at Merry Farm Pottery, 2-5p / More Info

• 🌱 Building a Local Food Movement: Organic and Regenerative Ideas in Practice at MV Agricultural Hall, 5-6:30p / More Info / Free, registration helpful

  The conversation explores practical organic and regenerative approaches to strengthening local agriculture and food systems.

• 🇵🇹 Portuguese American Feast at Portuguese American Club, 5-10:30p / More Info

  Traditional food, music, dancing, and community festivities continue across both days, all are welcome.

• 😂 Laughing Matters 2nd Annual Comedy Fundraiser for Stillpoint at MV Performing Arts Center, 7-8p / More Info / $25-$65

  Bluebird Improv creates a fully unscripted show inspired by conversations with the audience, with proceeds supporting Stillpoint’s programs. Ticket purchase is required.

Buy Tickets for Laughing Matters #ad

Sunday, July 19, 2026

• 🙏 Womanists at the Inkwell 2026 at Union Chapel, 8a / More Info / Register

  The gathering includes worship, Bible study, keynote speakers, workshops, and fellowship centered on womanist theology.

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🇵🇹 Portuguese American Feast Parade in Downtown Oak Bluffs, 11:30a / More Info

• 🎶 Sundays in the Park Concert featuring Pat Law and ESP at Ocean Park, 5:30-7:30p / Free

• 📖 Author Talk: Christin Geall — Flora Culture at Chilmark Community Center, 7-8:30p / More Info / $65 / Registration Required

Read more

⏱️ This Week on MVacay

I updated this guide for 2026 with all kinds of new information throughout:

I added a new Activity Category to my site, including this new experience (discount code inside!):

🗺️ What To Do This Weekend

The Thursday Events today and next week look PACKED. MVacay Weekend Updates are Fri-Sun, but you can find Mon-Thurs events all behind the paywall for the coming week.

Friday, July 10, 2026

• Vineyard Cup Regatta and Fluke for Luke Tournament Weekend Begin

• 🪶 Chilmark Community Trust: Wampanoag Traditions with Brad Lopes at The Yard, 1:30-3:30p / More Info
  Create pinch pots and corn dolls while learning about Wampanoag traditions; open to all ages, bring your own picnic.

• 🎩 Magic Show with Daniel Jay at Katharine Cornell Theater, 5:30p / free
  A free, family-friendly magic show presented by Vineyard Haven Public Library; no tickets or reservations required.

• 🎶 Sunset Concert Series: Mike Benjamin at Trinity Park Tabernacle, 6-7:30p / More Info / free-will offering

• 💃 Cirio Collective: Open Ground — Showing and Discussion at MV Performing Arts Center, 7-8:30p / More Info / donations accepted

• 🎬 Drive-In Movie: The Breakfast Club at The Vineyard’s Drive-In at the YMCA, 8:30p / More Info / pay-what-you-can ticketing, suggested $40 per car

Buy House Tour Tickets Here #ad

Saturday, July 11, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info / Free

• 🛍️ Camp Ground Flea Market at Trinity Park Tabernacle, 9a-1p / More Info
  Browse antiques, furniture, pottery, books, jewelry, household goods and more.

• 🐓 Barnyard Buddies (age 2-5) at The FARM Institute, 9:30-10:30a / More Info / $25/non-member pair

• 🐟 Annual Seine Net Event at State Beach, Little Bridge, 10-11:30a / More Info / free
  Join Great Pond Foundation scientists to help discover and identify marine life caught in a beach seine.

• 🪧 Seawall Stand at Vineyard Haven Seawall (with CONNECT to End Violence), 10a-12p / More Info

• 🎵 Kids Music Time at West Tisbury Town Hall Playground, 10-10:30a / donation-based (Tuesdays too)

• 🐴 Misty Meadows Saturday Pony Rides at Misty Meadows Equine Learning Center, 10a-12p / More Info / $30 registration required

• 🎭 The Fabulists at Tisbury Amphitheater, 10a / More Info / suggested $10 for adults, $5 for kids

• 🐐 Goat Yoga MV at Native Earth Teaching Farm, 11a-12p / More Info / $30 registration required

• 🇺🇸 Presidents for Kids at The Carnegie: Exploring Leadership & History at The Carnegie, 12-4p / More Info / free

• 🪶 An Introduction to Nôepe History – What is the Wampanoag history of MV? at Oak Bluffs Public Library, Downstairs Meeting Room, 12-2p / More Info

• 📚 One Book, One Island: Discussion of David McCullough’s 1776 at West Tisbury Public Library, 3-4p / More Info / free

• 🎶 The Variety Show for Island Elderly Housing at Featherstone Center for the Arts, 6-8p / More Info / $125

Buy Tickets for Laughing Matters #ad

Sunday, July 12, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🎭 Merrily We Roll Along with James Lapine at MV Film Center, 4p / More Info / $18 general admission, $12 child
  Screening of the Broadway musical production followed by a Q&A with playwright/director James Lapine.

• 🎶 Sundays In The Park Concerts at Ocean Park, 5:30-7:30p / free + Vineyard Haven Band Concert At Ocean Park at 7:30

• 📚 Author Talk: Tayari Jones at MVPAC, 7-8:30p / More Info / $75
  Tayari Jones discusses her novel Kin in conversation with journalist Michele Norris.

• ⚾ Edgartown Resident Appreciation Night + Hat Giveaway at MV Sharks at Shark Tank: MVRHS, 7:05p / More Info
  Cheer on the MV Sharks as they take on the Danbury Westerners, with a hat giveaway for Edgartown Resident Appreciation Night.

Read more

🗺️ What To Do This Weekend

Friday, July 3, 2026

• 🎣 Family Fishing at OB Fishing Pier, 9:30-11:30a / More Info

• 🫧 Bubble Fest at Oak Bluffs Public Library, 10-11a / More Info

• 🎨 First Friday Vineyard Haven at Downtown Vineyard Haven & Owen Park Beach, 10a-10:30p / More Info

  • 10a-2p: Daytime Art Market on Beach Street Extension, plus Art Hang at Althea Designs.

  • 12-4p: Live music and street performances around Beach Street Extension, Main Street, and Linden Tree Park.

  • 5-9p: Food trucks open at Owen Park. Live music at Owen Park Beach, including LooseFit, The Cut, Luke Dunlap, and Red Night Delight.

  • 9-10:30p: Silent DJ Party at Owen Park Beach with PathwaysARTS.

  • Downtown shops and galleries stay open late with gallery strolls, specials, and pop-ins throughout Vineyard Haven.

• 📚 Book Signing: A Weekend at Gramps ‘97 by Dave Mercaldo at Edgartown Books, 11a-1p / More Info
  Meet author and MVRHS alum Dave Mercaldo as he signs his nostalgic New England-set novel for middle grades.

• 🛍️ LoveShackFancy Pop-Up at The Charlotte Inn, 11a-4p / More Info (Sat too)

• 🎭 Seven Spools of Thread the Musical at The Strand Theatre, 2-4p / More Info

• 🎶 Joint Show: Vineyard Sound & Cape Harmony at United Methodist Church, 5p / More Info

• 🎶 Sunset Concert Series - Sean McMahon at Tabernacle, 6-7:30p / More Info

Saturday, July 4, 2026

• 🏊 Polar Bears of MV Celebrate 80th Anniversary at Inkwell Beach, 7:30-8:30a / More Info / free

• 🏃 Mike’s Run the Chop Challenge at Tisbury School, 8:45a / More Info

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info / Free

• 🎉 Children’s Fourth of July Parade at MVCMA, 9-11a / More Info

• 🇺🇸 25th Annual Aquinnah 4th of July Parade at Moshup Trail and Aquinnah Circle, 10a-3p / More Info
  Decorate your vehicle, join the parade, and stick around for kids’ games, awards, music, and BBQ at the Vanderhoop Homestead.

• 🧵 Embroidery with Havenly at Erica Wilson, 10a-4p / More Info (Sun too)

• 🎺 Polar Bears Present Community Concert at Ocean Park, 3-5p / More Info / free

• 🎉 Fourth of July Parade at Downtown Edgartown, 5p / More Info

  • Parade steps off from Edgartown School at 5p sharp. Route begins at West Tisbury Road and Robinson Road, then continues through Main Street, Pease’s Point Way, Morse Street, Fuller Street, Thayer Street, North Water Street, and back up Main Street to finish at Edgartown School.

  • All downtown roads close at 4:15p; traffic is prohibited from accessing Lower Main Street and the north side of town.Parade-route traffic is prohibited from 4:30-7p, so plan for delays and arrive early. No public parking at Edgartown School or the Library; both are for parade staging only. Handicap parking is available on Pine Street.

  • Taking the VTA? During parade road closures, use the temporary Edgartown stops at Great Harbor Market/Curtis Lane, Edgartown Hardware, or South Water & High, depending on your route.

  • Chappy Ferry vehicle traffic is prohibited starting at 4:15p, though service continues for vehicles already in line on Simpson Lane and Daggett Street.

• 🎶 Fourth of July Patriotic Sing-Along at St. Andrew’s Episcopal Church, 6:30p / More Info
  Join Vineyard Sound directly after the parade for the Star-Spangled Banner and a community sing-along.

• 🎵 Island Community Chorus Concert at Trinity Park Tabernacle, 7p / More Info

• 🎆 Fourth of July Fireworks at Edgartown Harbor, after dark / More Info

  • Fireworks begin after sunset, once it is completely dark. Best viewing is around Edgartown Harbor; the fireworks barge is moored north of the lighthouse, though it may be farther out depending on shorebird nesting.

  • North Water Street closes after the parade, with all vehicle access to North Water prohibited at 7:45p. Handicap parking is available in the EYC/Dock Street parking lot.

  • Taking the VTA for fireworks? Use Route 11 at Rockfish on North Water Street for pick-up/drop-off instead of Mayhew Lane; it’s the key downtown bus stop for getting out of Edgartown after the fireworks.

Sunday, July 5, 2026

• 🧹 Community Beach Cleanup & Trash Tally at State Beach in Oak Bluffs & Edgartown, 8-11a / More Info

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🏛️ Maintaining Our Sovereignty at Aquinnah Cultural Center, 11a-4p / More Info
  Visit the Wampanoag History Museum’s rotating exhibition centering contemporary Aquinnah Wampanoag sovereignty, history, and survivance (Fri+Sat too)

• 🧘 Restorative Sound Journey at Peaked Hill Studio, 4-5:15p / More Info / $30-$45
  Relax with a restorative sound bath using Himalayan and crystal singing bowls, monochords, chimes, and other instruments.

• 🎨 Art in the Park | Vineyard Cottages Reception at PA Club, 5-7p / More Info /
  Don’t miss the Auction After Party featuring art, community, and summer celebration at the PA Club.

• 🎶 Sundays In The Park Concerts at Ocean Park, 5:30-7:30p / free

Read more

🗺️ What To Do This Weekend

Friday, June 26, 2026

• 🐚 Seashore Discovery at Felix Neck Wildlife Sanctuary, Edgartown, 10-11:30a / More Info

• 🚜 1st Annual Farm Day at farms across MV, 10a-5p / More Info / Free
  Explore farms across the island through a full day of guided tours, including Edible and Medicinal Weed Walk, North Tabor Farm Tour, Whippoorwill Farm Tour, IGI Regenerative Farm Tour, Morning Glory Livestock Tour, Morning Glory Vegetable Tour, and Beetlebung Farm Tour.

• 🌺 Birthday Party at Nomans, Oak Bluffs, 11a-10p / More Info

• 🎨 Botanical Eco Printing with Katama Murray at Featherstone Center for the Arts, Oak Bluffs, 2-5p / More Info / $80

• 🖼️ Artists’ Premiere: Nancy Aronie, Cindy Kane, Marthe Rowen, Whitney Cleary at Granary Gallery, West Tisbury, 4-6p / More Info / Free

• 🦋 Fifth Annual Long Point Wildlife Refuge BioBlitz at Long Point Wildlife Refuge, West Tisbury, 5-10:30p (Sat too) / More Info / Free
  Join a 24-hour community science event with iNaturalist training, a family-friendly Moth Ball, nighttime moth surveying, and Saturday wildlife walks.

• 🎭 Little Women Play at Katharine Cornell Theater, Vineyard Haven, 7-9p / More Info / $20

Saturday, June 27, 2026

• 🧘 Morning Brews and Yoga at Island Autism Group, Hub House Porch, West Tisbury, 8:30-10a / More Info / $40

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🌿 The Art and Science of Pressing Plants with Emily Ellingson at Polly Hill Arboretum, 9a-12p / More Info / $40

• 🛍️ Chilmark Flea Market at Flea Market Field, Chilmark, 9a-2p / More Info / Free
  Shop the island’s oldest outdoor flea market for antiques, vintage finds, imports, jewelry, art, pottery, clothing, and handmade goods. Wednesdays too.

• 🧁 10 Years of Conrado at Conrado, 2 Union St., Vineyard Haven, 10a-6p / More Info / Free

• 🐴 Misty Meadows Saturday Pony Rides at Misty Meadows Equine Learning Center, West Tisbury, 10a-12p / More Info / $30

• 🎲 Summer Saturdays at the Library at Aquinnah Public Library, 12-3p / More Info / Free
  Drop in for outdoor games, activities, popsicles, and refreshments for kids and families.

• 🎉 MV Library Association Summer Reading Kick Off Party at MV Regional High School, Oak Bluffs, 3-5p / More Info / Free
  Celebrate the start of summer reading with bounce houses, face painting, fabric crafts, lawn games, hair tinsel, and DJ Dern of Vineyard Spin.

• 🖼️ Artist’s Premiere: Rachael Cassiani, Susie White, James Carter and Kenneth Pillsworth at Field Gallery, West Tisbury, 4-6p / More Info /

• 🎭 5th Annual MV Diversity Coalition Truth & Joy Celebration at MV Performing Arts Center, Oak Bluffs, 5-7p / More Info / Free
  Celebrate the island’s diversity with presentations, performances, awards, film premieres, and light refreshments from the MV Diversity Coalition.

• 👗 Clothes to Go’s Third Annual Fashion Show at Trinity Park Tabernacle, Oak Bluffs, 7p / More Info / Free
  Local models showcase creative second-hand styles in a family-friendly fashion show celebrating Clothes to Go’s community impact.

• 🎶 One Night Stand with Brazilian Vocalist Gabi Silveira at The Strand Theatre, Oak Bluffs, 7:30-9p / More Info / $25

Sunday, June 28, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 📸 15th Anniversary Photo Salon Show with Guest Curator Michael Johnson at Featherstone Center for the Arts, Oak Bluffs, 12-4p / More Info

• 🎨 Featherstone’s 30th Anniversary Open House at Featherstone Center for the Arts, Oak Bluffs, 1-4p / More Info
  Explore Featherstone’s campus, studios, and creative spaces with demonstrations, hands-on opportunities, and a Silent DJ with PathwaysArts on the lawn.

• 🧘 Sound Bath with Anna Marden at Stillpoint, West Tisbury, 4-5p / More Info / $20-$40

• 🎶 Sundays In The Park Concerts at Ocean Park, Oak Bluffs, 5:30-7:30p / / Free
  Bring a chair or picnic and enjoy live music by the sea during this weekly Sunday evening concert series.

• 🎬 The Airwaves Belonged to the People: WBCN and the American Revolution at MV Film Center, Vineyard Haven, 7:30-10p / More Info

• 🎶 Sundays In The Park Concerts at Ocean Park, 5:30-7:30p / free

• 🎺 Vineyard Haven Town Band Concert at Oak Bluffs Gazebo, 7:30-8:30p / More Info

Read more

🧳 Announcing MVacay’s Guest Travel Guide

I created an editable ~30-page guest travel guide for anyone hosting wedding guests, Airbnb guests, rental home visitors, friends, or family on MV. Purchase it as a ready-made welcome guide, then customize it with your own recommendations and host tips before sharing it privately with guests attending your wedding, event, rental stay, or hosted visit.

It is designed to help guests feel prepared before they arrive with travel logistics, town cheat sheets, food ideas, activities, beaches, rainy day options, and more. It combines about 15+ MVacay guides into one doc for easier sharing. Use the code MVACAY for 10% off.

Buy MVacay's Host+Guest PDF on Etsy Here

In the new post, I also shared a few of the actual messages I send guests before their visits so you can help your guests feel prepared:

⏱️ This Week on MVacay

I’m always updating what’s new in this guide below! ⬇️

A reminder you can always use code MVACAY15 for an Insect Shield discount. This guide is always free to use as a resource:

🗺️ What To Do This Weekend

Friday, June 19, 2026 - Juneteenth

• 🛍️ Bee Blunt Flagship Store Opening at 16 Union St. Suite A, Vineyard Haven, 10a-6p (all weekend, Sun 12-5).

• 🌸 Blooming Art at The Old Mill, 10a-3p / More Info / $20
  View floral arrangements inspired by artwork from Island artists during this MV Garden Club fundraiser.

• 🌊 Juneteenth At The Inkwell at Inkwell Beach, 3-6p / More Info / free
  Celebrate Juneteenth at historic Inkwell Beach with music, games, water sports, refreshments, and community fun.

• 🎤 Vineyard Gazette Presents: Juneteenth on MV Panel Discussion at Union Chapel, 3:30-4:30p / More Info / free
  A Juneteenth panel explores the meaning of freedom from the Revolutionary era through emancipation and today.

• 🎬 Toy Story 5 at Strand Theatre, 4:30p & 6:30p

Saturday, June 20, 2026

• 🖼️ Galaxy Arts Art in the Park at Sunset Lake in Oak Bluffs, begins today (online auction bidding thru July 4)

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🐚 Family Shellfish Day at Lagoon Pond Family Area, 9-11a / More Info

• 📸 Free Father’s Day Photos at West Tisbury Library, 9:30-11:30a / More Info / free

• ⚓ Harbor Fest 2026 at Oak Bluffs Harbor, 10a-6p
  Celebrate Oak Bluffs with live music all day, more than 50 vendors, local artisans, merchants, food, and entertainment.

• 🍓 Strawberry Festival at Morning Glory Farm, 11a-3p / More Info
  Celebrate strawberry season with shortcakes, donuts, burgers, hot dogs, cheese fries, live music, hay rides, crafts, and games for kids.

• 🦈 Jeffrey Kramer: On Jaws, Life and the Island at MV Museum, 1-2p / More Info / $30
  Actor Jeffrey Kramer shares stories from filming Jaws, his career, and his personal connection to the Island.

• 🎶 Juneteenth Concert at Edgartown Public Library, 1-2p / More Info / free

• 🎉 Juneteenth Jubilee Freedom & Joy Cultural Festival ’26 at Union Chapel, 1p / More Info / free

• 🦈 The Shark Is Still Working: A Jaws Documentary at MV Museum, 3-5p / More Info / $25

• 📚 Washashore Writers Volume Two Reading at Featherstone Center for the Arts, 4p / More Info / free

• ☀️ Aquinnah Solstice Celebration at Aquinnah Circle, 4-7p / More Info / free

• 🦈 Return to Amity: A JAWS Regatta & Amity After Dark Celebration at Wharf Pub, 5p-1a / More Info / $135
  Meet Jaws cast, crew, authors, and fellow fans for book signings, cosplay and impersonation contests, a live band, memorabilia, food, and an Amity After Dark party.

• 🎻 The Arborio Duo at Slough Farm, 5-6:30p / More Info / $35

• 🎟️ Friends of the Up-Island Council on Aging Fundraiser at Portuguese-American Club, 5-8p

• ⚾ Sharks Night: Jaws Night + MV Bank at MV Sharks, time TBD / More Info

Sunday, June 21, 2026 - Father’s Day

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• ⛪ Union Chapel Juneteenth Church Service at Union Chapel, 10a + Walk to Water Ceremony following / More Info

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info

• 🍳 Father’s Day Luncheons at both Alchemy and 11 Circuit

• 🎶 Vineyard Gazette Presents: Juneteenth Gospel Brunch 2026 at Edgartown Yacht Club, 12p / More Info / $130

• 🧴 Rona’s Self Care Products Pop-Up at Peaked Hill Studio, 2-4p / More Info / free

• 🍽️ Taste of Juneteenth at Portuguese-American Club, 2-5p / More Info / $75

• 🎵 Community Sing at Tisbury Amphitheater, 5-6p / More Info / free

• ⚾ Sharks Night: Woman in Sports Night with Lululemon at MV Sharks, 7p / More Info

• 🎶 Sundays In The Park Concerts at Ocean Park, 5:30-7:30p / free

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⏱️ This Week on MVacay

Five years of PRIDE in OB! I’m grateful to be working with the Oak Bluffs Association again this year to create their Pride Guide, and hope to see you there! Additions I’m excited for this year: a glitter bar, a photo booth, and their first ever online auction starting tomorrow:

When a visitor asks me “What should I DO?” this is my most comprehensive guide to share. It simply lists and links all my ideas in categories, and is in free access to everyone:

🗺️ What To Do This Weekend

Friday, June 12, 2026

• 🏳️‍🌈 Pride Kick Off Party at lululemon Edgartown, 5:30-7p / More Info
  Set the Pride vibes with a playlist, disco balls, glitter freckles, friendship bracelet making, an NA spritz bar and lululemon Pride products available.

• 🎟️ Concert: Emily King at The Strand Theatre, 8p / More Info / $45

• 🏳️‍🌈 Drag Queen Party at The Ritz Café, 10p
  Meet queens Larissa Montes and Missy Steak at the door, then kick off Pride Weekend with music from Dukes of Circuit Ave.

Saturday, June 13, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info

• 🏳️‍🌈 Drag King Storytime with Benjamin Clover at West Tisbury Public Library, 9:30a

• 🎪 Chilmark Church Children’s Fair at Chilmark Church, 10a-12p / free
  Kids can enjoy pony rides, face painting, cupcake frosting, games, a bounce house, bubbles and more.

• 🎨 Children’s Crafting: Father’s Day (Ages 6+) at Featherstone, 11a-1p (June 20 too) / More Info / $35

• 🏳️‍🌈 Parade Pre-Game + Face Painting/Glitter Bar at The Ritz Café, 12p

• 🧺 West Tisbury Town Picnic at Grange Hall, 12-2p

• 🏳️‍🌈 Pride Parade Lineup at Island Queen Ferry Terminal, 2p

• 🏳️‍🌈 Pride Parade begins from Island Queen Ferry Terminal, 3p
  March through downtown Oak Bluffs from the harbor to Ocean Park.

• 🏳️‍🌈 Live Music + Community Organizations at Ocean Park, 4-6p
  Enjoy performances, community booths (organized by QueerHubMV and MV Community Services) and a festive gathering in Ocean Park after the parade. Live music by The Femmes Band and Lexastential Crisis at the Ocean Park Gazebo and a Vineyard Social Booth photo op.

• 🏳️‍🌈 Pride Happy Hour and Food Specials at The Ritz Café, 4-6p

• 🏳️‍🌈 Black Eyed Susans + DJ SKRRRRT at The Ritz Café, 8p + 10p

• 🎭 Bloomsday at Katharine Cornell Theater, 8p / More Info / $25

Sunday, June 14, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p

• 🎨 Vineyard Artisans Festival at Historic Grange Hall, 10a-2p / More Info / free
  Shop directly from Island artisans at this weekly juried art show featuring handmade work and demonstrations.

• 🏳️‍🌈 A Drag Revue Royale at Red Cat Kitchen, 11a + 2p / More Info
  Celebrate Pride with live cabaret, drag kings and queens, comedy, choreography and an audience lip-sync battle.

• 🏳️‍🌈 Black Joy Kitchen Drag Brunch at Black Joy Kitchen, 11a + 2p / More Info
  Celebrate Pride at a queer-owned restaurant with food rooted in the Black Diaspora, drag performances, laughter, community and chosen-family joy benefitting the Oak Bluffs Association.

• 🎉 II June Festival of Joy at Saint Augustine Church Parking Lot, 12:30-6p
  Bring the family for traditional food, fun games, square dancing and more, hosted by Good Shepherd Parish MV.

• 🧘 Super Sound Bath with Priscilla Warner and Alison Leipzig at Stillpoint, 4-5p / More Info / $30-$60

• ⛪ Between the Oaks Outdoor Church at First Congregational Church of West Tisbury, 4:30-5:30p / More Info

• 🎶 Sundays In The Park Concerts at Ocean Park, 5:30-7:30p / free

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