🗺️ 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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Behind all of that convenience is a LOT of research and writing. I keep as much of MVacay free and accessible as I can, but I can only keep doing this with the community’s financial support. As a little thank you to locals, anyone who becomes a paid subscriber during the off-season gets 25% off forever.

Get 25% off forever

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

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⏱️ 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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The Vineyard has plenty of restaurants that keep the lights on long after summer ends, and this guide pulls them all together 🙂

Everything is organized by town, with winter closure and break dates included when available. I’ll continue updating this list as closuredates are confirmed.

❄️ What’s Open During the Winter MV

Vineyard Haven

Currently Open:
9 Craft Kitchen, Beach Road, Black Dog Bakery Café, Black Dog Cafe, Black Dog Tavern, Bobby B’s, Catboat Coffee Co., First Light Café, Island Fresh Pizza, La Choza, La Strada, Mad Martha’s Ice Cream (closes 11/1), Mikado, Nat’s Nook, Net Result, Ocean Club, Porto Pizza, Quitsa Kitchen, Rocco’s, S+S Kitchenette, Salvatore’s, Scottish Bakehouse, Sweet Bites, The Attic, The Maker, Toccopuro Coffee, Vineyard Grill, Waterside Market, Wolf’s Den, Woodland Variety, Yommi

Closed for the Season, Permanently or Temporarily Closed:
Art Cliff Diner, El Barco Taqueria, Fish MV, Grace Church Lobster Rolls, John’s Fish Market/Sandy’s Fish & Chips, Pie Chicks, The Wave Restaurant & Bar

Edgartown

Currently Open:
19 Raw Oyster Bar (closes 10/31), Alchemy, Bad Martha Brewery (expected to close late October; date TBD), Behind the View, Bettini, Black Sheep, China House, Cozy Corner Cafe, Dairy Queen, Dip 02539 Coffee Shop, Dock Street Coffee Shop, Edgartown Diner, Edgartown Meat + Fish, Edgartown Pizza, Edgartown Seafood, Espresso Love, Great Harbor Market, Indigo Indian Restaurant, Katama General Store, Katama Kitchen (closing soon; date TBD), L’Etoile, Mad Martha’s Ice Cream (closes 11/1), Morning Glory Farm, Morning Glory Farm Food Truck, Newes From America, Pelican Club (closing date TBD), The Quarterdeck, Rockfish, Rosewater, Soigne, Square Rigger, Terrace, The Fish House Market (closes 12/31), The Wharf, Toccopuro Coffee, Town MV, Wicked Burger

Closed for the Season, Permanently or Temporarily Closed:
Among the Flowers Cafe, Atlantic Fish & Chop House, Atria Restaurant & Brick Cellar, Behind the Bookstore, Blackbird Café, Chesca’s Restaurant, Détente, Lucky Hank’s, MacPhail’s Corner Cafe, The Covington, The Dunes at Winnetu, The Fish House Takeout, The Port Hunter, The Seafood Shanty

Oak Bluffs

Currently Open:
11 Circuit Restaurant & Bar (expected to close late October; date TBD), The Alley, Aquila at the YMCA, Bangkok Thai, Barn Bowl + Bistro, Ben & Bill’s Chocolate Emporium, Big Dipper Ice Cream & Deli, The Black Dog Dockside Café, The Black Dog Pub, Black Joy Kitchen, Carousel Ice Cream Factory, Coop de Ville (expected to close late October; date TBD), Esh MV, Farm Neck Café, Fat Ronnie’s (closes 10/31), Fishbones Bar & Grille, The Highlands General Store, Honorary Tavern, Inkwell Beach Club, Jimmy Seas Pan Pasta, Lookout Tavern (closes 12/31), Mad Martha’s Ice Cream (closes 11/1), Midnight Taco & Tequila Bar, Mo’s Lunch, Mocha Mott’s, MV Chowder Company, Nauti Cow MV, Offshore Ale, Pawnee House, Red Cat Kitchen (closes 12/31), Sharky’s, Sweet Life Cafe, The Food Truck at MVY Arena, The Ritz, Toccopuro Coffee, Tony’s Market, Vineyard Caribbean Cuisine, Winston’s Kitchen

Closed for the Season, Permanently or Temporarily Closed:
Aalia’s Coffee, Biscuits, Giordano’s Restaurant, Giordano’s Takeout, Jetty Beach House, Midnight Mediterranean, MV Salads, Nancy’s Restaurant, Nancy’s Snack Bar, Nomans Restaurant, Rosie’s Frozen Yogurt, Sand Bar & Grill, The Good Shoppe, Tigerhawk Sandwich Co.

Up-Island

West Tisbury, Chilmark + Aquinnah

Currently Open:
7a Foods, Aquila Café (expected to close late October; date TBD), Beetlebung Farm, Menemsha Fish Market, Menemsha Market, Plane View Restaurant, Restaurant Foster at Lambert’s Cove Inn, State Road, Vineyard Take Out

Closed for the Season, Permanently or Temporarily Closed:
Chilmark General Store, Chilmark Tavern, Home Port Restaurant, Larsen’s Fish Market, Menemsha Galley, Outermost Inn dinner

2026-2027 Expected Change Notices

• Orange Peel Bakery has permanently closed.

• Lucky Hanks is permanently closed.

• Murdick’s Fudge locations permanently closed across the island.

Another reputable list of closure dates can be found here.

More Food Recs:

⏱️ 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

🌅 September

Things to Do Anytime

• Try a farm or food class — Slough Farm, FARM Institute or another fall workshop.

• Drive to Menemsha for a sunset and stop into the newly re-opening Menemsha Store.

• Catch a film at the MV Film Center or a live performance at MV Playhouse.

• Have dinner somewhere that was almost impossible to get into in July or August.

• Check out the renovated Vineyard Haven Library.

• Watch a Derby weigh-in in Edgartown + go to Derby Kids Day.

• New Eats: Try Morning Dew + Yommi at their new State Road storefront or revisit The Net Result after its major renovation.

Dates to Know

• September 18–19 – Behind the Curtain With the Nashville Hit Makers at The Strand Theatre

• September 19 - Tivoli Day

• September 20 – Derby Kids Day at the OB Pier

• September 30 – Arnie Reisman Poetry Café at MV Playhouse

🎃 October

Things to Do Anytime

• Take a fall foliage walk at Mytoi Gardens or Polly Hill Arboretum.

• Do a DIY farmstand crawl — pumpkins at Morning Glory Farm + stops at North Tabor Farm, North Tisbury Farm and Mermaid Farm.

• Do a thrift + vintage loop for fall clothes, home finds or donations.

• Walk the permit-only beaches that reopen for fall, including Lambert’s Cove and Lucy Vincent.

• New Eats: Try Restaurant Foster + Mermaid Bar at Lambert’s Cove Inn.

Dates to Know

• October 3 – Family Day at the PA Club / Ponies & Pumpkins at Misty Meadows / Ladyfest

• October 10–11 – Vineyard Artisans Fall Festival

• October 12 – Indigenous Peoples’ Day / Sweet Life Author Series: Joseph Lee

• October 17 – Pumpkin Festival at Morning Glory Farm / Children’s Day for Our Children of the Island

• October 24 – Harvest Festival with the Ag Society

• October 25 – Happy Haunting Edgartown

• October 31 – Halloween in Oak Bluffs: OBA + Flying Horses + OB PTA Trick or Treating

🦃 November

Things to Do Anytime

• Shop the first holiday markets and gift shows, including Featherstone.

• Sign up for an adult learning workshop or library program.

• Volunteer with an Island organization before the holidays.

• Learn one Vineyard skill — tie a fly, blow glass, make cheese, cook with a farmer, etc.

• Visit the new exhibits at the Martha’s Vineyard Museum.

• Do a fall gallery/studio crawl - Granary Gallery, Knowhere, MV Glassworks

• New Eats: Try the The Wave in Vineyard Haven for a sunset dinner.

Dates to Know

• November 7 – Barn Raisers Ball with the Ag Society

• November 11 – Veterans Day

• November 27–28 – Vineyard Artisans Thanksgiving Weekend Festival

• November 28 – Chowder Cup Edgartown / Small Business Saturday

🗺️ 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

Last Updated October 23, 2026.

📅 2027 Confirmed Event Dates on Martha’s Vineyard

As always, dates can change, so confirm directly with the event organizer when making plans.

• March 6, 2027 - MV Winter Classic and Amity Relay Race

• March 31–April 4, 2027 - Martha’s Vineyard Film Festival (Circuit Arts)

• March 28, 2027 - Easter Sunday

• April 24, 2027 - MV Spring Classic Marathon and Half Marathon

• May 31, 2027 - Memorial Day

• June 12, 2027 - MV Pride Parade

• June 19, 2027 - Oak Bluffs HarborFest

• June 19, 2027 - Juneteenth

• July 4, 2027 - Edgartown Fourth of July Parade + Fireworks

• July 8, 2027 - Tisbury Street Fair

• July 18–24, 2027 - Vineyard Ease

• July 25-August 1, 2027 - Legacy Week on MV/HBCU Week on Martha’s Vineyard

• August 12–15, 2027 - Martha’s Vineyard Agricultural Fair

• August 18, 2027 - Grand Illumination Night at MVCMA (projected based on its established annual schedule; awaiting official 2027 announcement)

• August 20, 2027 - Oak Bluffs Fireworks Display (projected for the third Friday in August based on the town’s established schedule; awaiting official 2027 announcement)

• September 6, 2027 - Labor Day

• September 18, 2027 - Tivoli Day

• October 11, 2027 - Indigenous Peoples’ Day

• November 11, 2027 - Veterans Day

• December 4, 2027 - Light Up Oak Bluffs

• December 9-12, 2027 - Christmas in Edgartown (traditionally held the second weekend in December; awaiting official 2027 announcement)

📅 2027 Unconfirmed Event Dates on Martha’s Vineyard

• Events Typically in March (Unconfirmed): Meat Ball, Night Out for Nonprofits

• Events Typically in April (Unconfirmed): MV SWELL Lip Sync Contest at the PA Club, Misty Meadows Annual Egg Hunt, Annual Farm Institute Egg Hunt, MV Career & Networking Night at Grange Hall, MV Hospital Community Health Fair, Bivalve Ball at Chilmark Community Center, Earth Day Conservation Festival + Beach Cleanup with VCS, MV Spring Classic Marathon + Half Marathon

• Events Typically in May (Unconfirmed): Bike MS: Martha’s Vineyard, Aquinnah Variety Show at Aquinnah Town Hall, Porchfest Edgartown, Martha’s Party Event Conference, MV Environmental Film Festival (MV Film Society), Memorial Day Weekend Vineyard Artisans Festival, MV Garden Club Plant Sale at The Old Mill, MV SOUND, Edgartown Sidewalk Sale, MV Memorial Road Race, Blessing of the Fleet

• Events Typically in June (Unconfirmed): Juneteenth Events, Farmers Markets Begin, First Fridays Begin, Taste of the Vineyard, Blooming Art, Strawberry Festival at Morning Glory Farm, JAWS Reunion, Vineyard Cup Regatta, Fluke for Luke Tournament Weekend, Campground Flea at MVCMA Tabernacle, Island Elderly Housing Benefit Concert at Featherstone

• Events Typically in July (Unconfirmed): Cottagers House Tour at Cottagers’ Corner, MV Book Festival, Native Artisan Market + Festival at Aquinnah Circle, PA Club Annual Feast, HBCU Legacy Week

• Events Typically in August (Unconfirmed): MV Comedy Festival, Built on Stilts Festival, Martha’s Vineyard African American Film Festival, Chilmark Road Race, Black Education Forum, MV Black Book Festival, MV Vibe Fest at Waban Park, Martha’s Vineyard Soulfest, Gospel Benefit Concert, MV Jazz Experience

• Events Typically in September (Unconfirmed): Wind Festival at Waban-Alley Park, Aquinnah Wampanoag Powwow, MV Striped Bass + Bluefish Derby

• Events Typically in October (Unconfirmed): Family Day at the PA Club, Misty Meadows Ponies + Pumpkins, Vineyard Artisans Fall Festival, Pumpkin Festival at Morning Glory Farm, Harvest Festival with the Ag Society, Happy Haunting Edgartown

• Events Typically in November (Unconfirmed): Barn Raisers Ball with the Ag Society, Vineyard Artisans Thanksgiving Weekend Festival, Chowder Cup Edgartown, Small Business Saturday

• Events Typically in December (Unconfirmed): Light Up Oak Bluffs

💛 PSA: All MVacay posts and guides are original content. Please don’t copy, repost, or engage in digital plagiarism (including uploading to websites or AI systems) without permission. I’m always open to collaborations, ghostwriting, or licensing if you’d like to use my work the right way!

⏱️ 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

📬 Susan Branch Built a Vineyard Cottage-Core Empire

You would immediately recognize the work and influence of Susan Branch, but you may not know she was a seasonal resident of Vineyard Haven! Her mailed (yes, MAILED!) newsletter, Willard, reportedly grew from about 2,000 copies to 25,000 before going digital, long before online newsletters became a business model. Her iconic hand-lettering, recipes, calendars, books, and homey aesthetic became a whole cottage-core costal-grandmother industry, and she remains a beloved author.

🪑 Chicken Alley May Be the Highest-Grossing Thrift Shop Per Square Foot in the Country

I had heard Chicken Alley was unusually successful, but I didn’t realize how unusual: it has been described as the highest-grossing thrift shop per square foot in the United States, and in 2021–2022, it topped $1 million in annual sales for the first time.

💐 Second Bloom MV Repurposes the Wedding Flowers

On an island with so many weddings and events, it’s easy to look skeptically at the waste. Luckily, Rae Carter saw flowers from an East Chop Lighthouse wedding being discarded, and now repurposes arrangements go to people and places across the Island. These post-event destinations include the hospital, hospice, food pantry, senior centers, schools, libraries, and more. What a cool way to give back!

🐸 Vineyard Lingo: Pinkletinks and Beetlebung

I knew the words but not the backstory. “Pinkletink” is a Vineyard name for spring peepers, and “beetlebung” is the Island name for black tupelo, or black gum. Both are normalized local vocabulary, but they are tied to the Island’s spring sounds and native trees.

🎣 The First Derby Gave Away LAND as a Prize

The first Martha’s Vineyard Striped Bass Derby prize list feels almost unreal now. In 1946, one special prize for non-residents was a “lot of land on Martha’s Vineyard suitable for sportsman’s camp,” courtesy of Henry Cronig. Now, the prize winners receive a boat (or this year a Jeep), but winning land must’ve been so cool!

🤟 Chilmark’s Historic Signing Community

Martha’s Vineyard had an unusually high rate of hereditary Deafness from the 17th century into the early 20th century, but the part that stayed with me how many HEARING Islanders signed too. In the 19th century, 1 in 25 Chilmark residents were Deaf, and in Squibnocket in the 1870s and 1880s, that number was reportedly 1 in 4. In Chilmark especially, sign language was part of everyday communication, and Deaf community members were present in work, church, family, politics, and town life.

🧠 MV Has Generous Safety-Net Services

I know about a lot of amazing Island nonprofits, but some cool offerings I learned recently: there is free, same-day mental health support available through MV Community Services. Plus reproductive health care advocacy through MV SWELL, including funding tied to abortion access and vasectomy reimbursement. Availability, eligibility, and funding can change, so check directly with each organization.

🕷️ Don’t Forget to SAVE the Tick

Checking for ticks is step one, but SAVING a tick after a bite can be helpful too, especially if you are being cautious with kids. MV Medical recommends saving ticks for identification and testing, since knowing the type of tick can help guide next steps. On MV, where Alpha-Gal cases have climbed quickly, identifying whether it was a lone star tick can give you faster context than waiting to see if confusing symptoms appear later. It is not a replacement for medical care, and tick testing cannot tell you whether you will develop Alpha-Gal, but it can help identify the tick and test for certain tick-borne pathogens. If a tick was attached, contact a provider quickly; MV Medical notes that prophylactic treatment is most effective within 72 hours. You can mail ticks to services like TickReport; they generally ask you to save the tick in a small sealed container or zipper bag, ideally with a small piece of slightly damp paper towel.

✈️ Katama Airfield Is the Largest GRASS Airfield

Katama Airfield is described as the largest GRASS airfield in the country, with deep family ties that continue today. Its preservation is especially incredible: in the 1970s, the 128-acre field could have become roughly 120 housing units, but Steve Gentle refused to sell it off that way. Instead, the town, the Nature Conservancy, and the state eventually helped preserve it as an airfield. So instead of houses, the Katama Plains are a rare coastal sandplain grassland habitat whose plants and insects have adapted to salt spray, storms, and fire. Gentle’s grandson, Mike Creato, still runs Classic Aviators out of the airfield today.

🇧🇷 40%+ of Island Students Speak Portuguese at Home

Martha’s Vineyard has a large and growing Brazilian community. Some school data shows Portuguese is spoken at home by nearly HALF of Island students. More translation, outreach, and Portuguese-language services are being added across the Island. That makes Portuguese-language access a basic part of helping Island families feel informed, included, and welcome.

What impressed me most was how thoughtful the experience felt from start to finish. There were so many little details, the crew made a point to include every child, and parents could mostly sit back and enjoy the ride.

Here’s everything to know if you’re thinking about setting sail:

🏴‍☠️ About Pirate Adventures

Pirate Adventures of Martha’s Vineyard operates the Sea Gypsy X, a custom-built 40-foot pirate ship that sails from Oak Bluffs Harbor. The experience is designed specifically around kids rather than being a traditional boat cruise with a few children’s activities added on.

Before even boarding, kids are transformed into the ship’s newest pirate crew with pirate names, face painting, costumes and pirate training. Once underway, the group works through an interactive treasure-hunt story involving a treasure map, a message in a bottle, water cannons, a rival pirate and eventually a sunken treasure chest that the kids help pull from the water.

The full experience lasts about 90 minutes, with approximately 20 minutes of pirate prep on land and 70 minutes aboard the boat.

⚓ Our Pirate Adventure

Check-in was incredibly friendly and personalized. Before boarding, the girls got into character with pirate vests, face/hand painting and their new pirate gear. Once we were on the boat, there was very little downtime.

They were using both their brains and their bodies, and the activities changed frequently enough that even my three-year-old stayed engaged. The team also seemed very aware of making sure every child got a turn and felt included. We had a good-sized group aboard, but it never felt overcrowded or chaotic.

And as a parent, this was refreshingly easy. We were obviously still responsible for our children, but the crew really took over the entertainment. Rather than spending the entire outing trying to keep the girls occupied, we could mostly sit back, watch them participate and enjoy being out on the water.

The boat ride itself was mostly steady during our trip, and although there are water cannons involved in the adventure, we never got wet. And the girls were thrilled with what they came home with: treasure, a sword, bandana and eye patch. Between the boat ride, live entertainment, activities and take-home goodies, it felt like a really good value.

It also has the personal feel of a small, family-run business. Nothing about our visit felt thrown together or generic; from check-in through the final treasure hunt, it felt like they had really considered what would keep kids engaged and make the experience special.

🗒️ Visit Planning

📍 Location: Dockside Marketplace & Marina, 12 Circuit Avenue Extension, Oak Bluffs. Check in inside Dockside Marketplace at the Treasure Chest Pirate Shop before heading outside to the Pirates in Training staging area.

⏰ Length: Approximately 90 minutes total—about 20 minutes of pirate prep on land and 70 minutes at sea.

🧒 Ages: Pirate Adventures recommends the experience for ages 3–10. Based on our visit with a three- and four-year-old, I personally think ages 5–7 are probably the sweet spot, although both of my younger girls were able to participate and had a great time.

💲 2026 Pricing: $44 per child or adult; $25 for infants under 12 months. Everyone aboard needs a ticket. Pirate Packs: $15 add-on including a Pirate Adventures bandana, foam sword and eye patch. Vests and sashes used during the adventure are loaned for the trip.

📅 2026 Schedule: Sailings are currently offered Tuesday, Wednesday, Thursday and Saturday (some Sundays), with up to three departures per day depending on demand. The last date of sail for 2026 is September 6. Check the online booking calendar for the most current sailing times and availability, it’s typically 9:15a, 11:45a and 2pm.

🎟️ Reservations: Advance reservations are required, although walk-ups may be accepted when space is available. Plan to arrive by your listed booking time—the pirate prep begins before the boat departs.

🅿️ Parking: There is no dedicated Pirate Adventures parking, and summer parking around Oak Bluffs Harbor can be difficult. Give yourself extra time to find a spot; they cannot hold the boat for late arrivals.

🚽 Bathroom: There is no bathroom aboard the boat, so definitely make a bathroom stop inside Dockside Marketplace before sailing.

👶 Strollers: Strollers cannot go aboard because space is limited, but they can be stored at the pirate shop.

🧴 What to Bring: Water and sunscreen are recommended. You can bring small snacks and drinks, but no glass. A sweatshirt or light layer is also smart since it can feel cooler once you’re out on the water.

🌦️ Weather: They sail in many conditions, including light rain, but trips can be cancelled for heavy rain, thunderstorms, high winds or other conditions the captain considers unsafe.

Our experience was hosted by Pirate Adventures of Martha’s Vineyard. #gifted

⏱️ 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

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I also think there are thoughtful ways to make sure your event includes and supports the community you are arriving to. There are people here working year round to make this Island special. If you are planning something on Martha’s Vineyard, here are 10 ways I would encourage you to approach it:

🤝 Hire Island vendors whenever you can

There is an incredible network of people on Martha’s Vineyard who already know how to make things happen here. Before bringing every vendor over from off Island, see if a local photographer, planner, caterer, florist, musician, rental company, transportation provider, or other Island business can fill the role.

• Lis’s Tips: when working with island vendors, give them at least 2 months notice! This will ensure you can get fit into their schedule.

🎨 Pay Island creatives for their work

If you want Martha’s Vineyard represented in your branding, invitations, signage, merchandise, or social content, consider commissioning someone who actually creates here. Hire a local artist, license an Island photographer’s image, or work with a designer who knows the place rather than treating Vineyard imagery as something free to borrow.

• Lis’s Tips: on channels like Visit Martha’s Vineyard, note which photographers images you like and then look to see who is tagged. Reach out and describe the type of image you’d like to license, it’ll be a great nod to local talent and make your flyer beautiful! For video reach out to creators and see their rate for producing a reel with island B-roll for you.

📣 Include Island creators and community voices

If you are inviting media, influencers, creators, or tastemakers to your event, save some space for people who are already part of the Vineyard community. There are local writers, photographers, creators, business owners, and organizations who spend all year sharing and supporting what happens here.

Remember that Martha’s Vineyard is also a diverse, multilingual community, including a large Brazilian and Portuguese-speaking population. Consider translating invitations, flyers, social posts, or other outreach into Portuguese so more of the Island community can actually hear about and participate in what you’re creating.

🛍️ Source locally before bringing everything over

Welcome bags, gifts, flowers, food, favors, merchandise, and other event details are all opportunities to put some of your event spending back into the Island economy. You can introduce your guests to Martha’s Vineyard businesses at the same time.

• Lis’s Tips: Tote Bags from Toteally Yours, chocolate from Salt Rock, zucchini bread from Morning Glory, flowers from Donaroma’s are some of my favorites to receive over and over again.

🍽️ Make a plan for leftover food

Before the event, think about what will happen to food that is still safe and usable when everything wraps up. Depending on what you have, there may be an opportunity to share it with staff, volunteers, a community fridge, food pantry, or another Island organization rather than throwing it away.

• Lis’s Tips: the Island Food Pantry can accept closed food, Red House Peer Recovery Center can receive food donations I believe, there is a Free Fridge at the Hospital, or just ask in Free Stuff Martha’s Vineyard Facebook Groups.

💐 Give event leftovers a second life

Flowers, décor, furniture, clothing, merchandise, and other event materials do not necessarily need to leave on the ferry or end up in the trash. Consider whether flowers could brighten a local senior living community or whether usable items could be donated to a thrift shop, the family center, or another Island organization.

• Lis’s Tips: Second Bloom MV does repurposed flowers! Or reach out to the Council on Aging in your town.

❤️ Support an Island nonprofit or community organization

If Martha’s Vineyard is helping make your event special, I love the idea of directing a little of that benefit back into the community. That might mean making a donation, including a nonprofit partner, sponsoring something, or simply introducing your guests to an Island cause worth knowing about. If you’re not sure which organization is the best fit, the Martha’s Vineyard Chamber of Commerce is a great connector.

• Lis’s Tips: I love to donate to the Red Stocking Fund, Island Grown Initiative and MV Clothes to Go!

🗓️ Know what is already happening on the Island

Martha’s Vineyard has a very full community calendar, especially in the summer. Before choosing your date, take a look at what local organizations, businesses, festivals, and nonprofits already have planned so you understand what you are arriving into.

📍 Help your guests understand the Island they’re visiting

Your event may take place at one venue, but your guests will be navigating the entire Island. Help them understand ferries, transportation, parking, beaches, towns, restaurants, local etiquette, and the basics of getting around before they arrive.

MVacay’s customizable Host Guide is designed for exactly this. Hosts can purchase a guide, personalize it for their event or group, and give guests a local resource to help them feel oriented while also directing them toward Island businesses and experiences.

Buy the Host + Guest Travel Guide

🌊 Leave the Island better than you found it

Martha’s Vineyard is a year round community that people work very hard to sustain. You do not have to be from the Vineyard to create something meaningful here. I just hope that when you do, some of your attention, spending, exposure, and resources stay with the Island and the people who make it the place you wanted to come to in the first place ❤️

⏱️ 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

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• 🗓️ Festival Dates: August 7–15, 2026

• 📍 All screenings take place at the Martha’s Vineyard Performing Arts Center, 100 Edgartown–Vineyard Haven Road, Oak Bluffs

• ℹ️ Registration and festival information begin daily at 10:30am

• ⚠️ The festival itinerary is subject to change without notice

Buy Tickets

🎬 Daily Schedule: What’s Playing + Where to Be

🗝️ How to Use MVacay’s Guide

• 🎬 = Film screening or film block

• 💬 = Conversation or panel following a screening

• 🛋️ = Vineyard Lounge Programming

• 🏆 = Festival nominee

• 🎉 = Party, reception, or special event

• 🎟️ = Individual tickets available

• ❌ = Passholder-only event

🛋️ Vineyard Lounge Programming

The Vineyard Lounge has a separate schedule of panels, conversations, screenings, and brand activations throughout the festival. Unless otherwise noted, Lounge events take place on the grounds of the Martha’s Vineyard Performing Arts Center.

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💡 I created this guide to help families like mine avoid the info overload. Instead of flipping through the 100 page fair book or missing something great, you can check this post for the full schedule, parent tips, food details, and more. Bookmark it, share it, and enjoy the Fair!

• 🗓️ Dates: Thursday, August 13–Sunday, August 16, 2026

• 📍 Location: Martha’s Vineyard Agricultural Society Fairgrounds, 35 Panhandle Road, West Tisbury

• 🎪 This year: The Martha’s Vineyard Agricultural Society celebrates its 164th Livestock Show & Fair with the theme Farm • Family • Fair.

• 🎟️ Ticket information, carnival ride details, daily schedules, Fair entry deadlines, and tips are included below.

🧭 Overview

Fair Hours:

• Thursday, August 13: 10a–11p / Cattle Day

• Friday, August 14: 10a–11p / Horse Day

• Saturday, August 15: 10a–11p / Farm Machinery Day

• Sunday, August 16: 10a–6p / Dog Show Day

🎡 Carnival rides open at 11a each day.

*This post was last updated Tuesday, August 10, 2026.

Buy Tickets to the Fair

Read the Fair Book

Buy Fiesta Rides Passes for Rides

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