⏱️ 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

• 🏳️‍🌈 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

Read more

⏱️ This Week on MVacay

My Rainy Day guide is now updated with current 2026 hours, prices, and several new additions as well. Just in time for a rainy Sunday. Stay dry 🫡

I’m so excited to celebrate Pride this year! More details here on how you can support:

Juneteenth, Father’s Day and Jaws events are all listed in the Save the Dates behind the paywall.

🗺️ What To Do This Weekend

Friday, June 5, 2026

• 🎨 First Friday Vineyard Haven at Vineyard Haven Harbor Cultural District, all day / More Info / free
  Celebrate Pride Month with a full day of community events, art, food, shopping, tie-dye, live music, a Pride flag raising, and a silent disco.

  • 10a-2p: Daytime Art Market on Beach St. Ext. feat Alex Elvin and Janet Newton

  • 4-5p: Mark Alan Lovewell & Molly Conole on Main Street

  • 4:45p: Pride Flag Raising

  • 5p: Sarah Shaw Dawson & Friends at Owen Park (5p), Jaywalkers at Owen Park (6:30p) Bella Bossa Nova & Samba at Owen Park (7:30p), Os Naftalinas at Owen Park (8p)

  • 9-10:30p: PathwaysARTS Silent Disco at Owen Park

• 🎵 Moss Henry in Edgartown at The Port Hunter, 10p-12a / More Info / free

Saturday, June 6, 2026

• 🥕 West Tisbury Farmers Market at MV Agricultural Hall, 9a-12p / More Info / free
  MV’s oldest open-air market returns with local farm goods, food, artisans, and community vendors. Wednesdays begin June 10th.

• 🌻 Sunflower Spirals: Kids Gardening at Slough Farm, 10-11:30a / More Info / free
  Kids ages 5-10 can help plant a sunflower spiral in the Friendship Garden and take home a seedling to care for.

• 🎨 Linocut Pet Portrait with Ann Meleney at Featherstone Center for the Arts, 10a-1p / More Info / $70

• 🌿 Wonderful Weeds at Native Earth Teaching Farm, 12-3p / More Info / free

• 🎶 Simply Schumann Concert at Stillpoint, 3p / More Info / $20
  Baritone David Behnke and pianist David Rhoderick perform Schumann lieder in support of MVCMS education programming.

• 🎬 Project Hail Mary at MV Film Center, 4p / More Info

Sunday, June 7, 2026

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

• 🫖 Tea and Poetry in the Rose Styron Garden at MV Museum, 11a / More Info /
  Enjoy poetry, tea, and conversation in the garden with Rose Styron and members of the Cleaveland House Poets.

• 💐 Brunch & Bouquets at The Pawnee House, 12-2p / More Info / Register first
  Build your own bouquet with Fire Cat Farm while enjoying a four-course brunch, wine pairings, and a special guest from Top Shell Oyster Farm.

• 🎓 MVRHS 2026 Graduation Ceremony at the Tabernacle, 1p

• 🍽️ The Island Table with North Tabor Farm at North Tabor Farm, 4p / More Info / $190
  A multi-course, family-style farm dinner celebrating Island farms, fishers, seasonal ingredients, and community.

• 💃 Local Off-Season Contra Dance with Live Music by The Flying Elbows at Unitarian Universalist Society of MV, Stevens Chapel, 4p / More Info / free

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

Read more

⏱️ This Week on MVacay

One commitment I’ve made to readers is to continuously go back and update old posts to reflect new information, closures, and the evolving landscape of MV. As we ramp up for the summer I’ve been focused on updating my full archive post-by-post.

I updated the Sunset/Sunrise guide with the annual Menemsha shuttle schedule:

I also updated our Oak Bluffs itinerary for 2026:

🗺️ What To Do This Weekend

Friday, May 29, 2026

• 🎶 Group Therapy Concert: Peter Halperin, Jim Orr and Hudson Bausman at West Tisbury Public Library, 3-4p / More Info / free

• 🎤 Christian Finnegan — Live Stand-Up Comedy at MV Film Center, 7:30-9:30p / More Info / $25

• 🎧 DJ Dextreme at Eleven Circuit, 9p-12:30a

Saturday, May 30, 2026

• 🐦 Birding 101 with Robert Culbert and Luanne Johnson at Manuel F. Correllus State Forest Headquarters, 8-10a / More Info

• 🏷️ Tag Sale with Rainy Day, The Green Room & Island Vintage at parking lot behind Rainy Day, Vineyard Haven, 10a-4p (Sun too)
  Shop discounts and sale finds from three Vineyard Haven shops; cash only and BYO bag.

• 🌿 Wonderful Weeds at Native Earth Teaching Farm, 12-3p / More Info / free

• 🎶 The Great American Songbook: Concert with David Mintz at Edgartown Public Library, 3-4p / More Info

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

• 🎣 Fly Rod Striped Bass Catch and Release Tournament at MV Rod & Gun Club, 7p-12a / More Info / $45

Sunday, May 31, 2026

• 🛍️ Oak Bluffs Open Market at Washington Park, 10a-2p
  Browse local produce, specialty foods, flowers, artisans, vintage finds and live music by Beach Plum Jam.

• 💃 RISE Presents 19th Annual Recital: Road Trip at MVPAC, 10a

• 🎨 The Vineyard Landscape Opening Reception at Featherstone Center for the Arts, 4-6p / More Info / free

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

• 📸 Seen/Unseen: Photo Walk at Lucy Vincent Beach, 7:15-8:15p / More Info / $10 contribution appreciated
  Join photographer Melissa Blythe Knowles for a dusk photo walk exploring fading light along the shoreline.

Read more

⏱️ This Week on MVacay

ALLLL the recurring live music for this summer is in this ONE handy guide:

I wanted to get this list started with the knowledge that I will add to it over time. If you think of someone who should be on the list, please comment or let me know:

I also wrote this story for BlueDot about CSAs this season on MV!

🗺️ What To Do This Weekend

Friday, May 22, 2026

• 🛍️ TGIF Super Clearance Day at Chicken Alley Thrift Shop, 10a-6p / More Info

• 🎨 MV Glassworks Studio Sale at Martha’s Vineyard Glassworks, 10a-4p (Sat-Sun too)

• 🌊 Tisbury School’s March to the Sea at Owen Park, 12:15-1p

• 🎶 Live Music with John O’Toole at Bad Martha, Edgartown, 4-6p

• 🎬 Star Wars: The Mandalorian and Grogu at The Strand Theatre, Oak Bluffs, 5:30-7:30p (+ 4 dates) / More Info / $10

• 🎭 Play: Woodcutters at MV Playhouse, 7p (Sat + Sun too) / More Info

• 🎭 Weekend of Women: One Act Play Festival at Katharine Cornell Theater, Vineyard Haven, 7:30p (Sat+Sun too) / More Info

• 🎶 Dock Street Fight Club at The Ritz MV, Oak Bluffs, 10p

Saturday, May 23, 2026

• 🌱 MV Garden Club Annual Plant Sale at The Old Mill, West Tisbury, 10a-2p / More Info (SUN too)
  Browse perennials, herbs, and garden favorites grown and selected by MV Garden Club members.

• 🛍️ The Great Annual Edgartown Sidewalk Sale at Edgartown Village Green, Edgartown, 10a-4p / More Info / Free

• 🎨 Vineyard Artisans Memorial Day Weekend Festival at The Grange Hall, West Tisbury, 10a-4p (Sun too) / More Info / Free

• 🛍️ Estate Sale at 651 State Rd, West Tisbury, 10a-2p (Sun too) / More Info

• 🎨 Memorial Day Weekend Craft Show at Portuguese-American Club, Oak Bluffs, 11a-4p / More Info /
  Several island makers gather at Mo’s Lunch with handmade crafts and local goods.

• 🐦 MVEFF: Short Films About Birds at MV Film Society, 1p / More Info

• 📚 Book Signing: The Summer of Second Chances by K.L. Walther at Edgartown Books, Edgartown, 2-4p / More Info

Sunday, May 24, 2026

• ⛵ Chilmark Church Blessing of the Fleet at Menemsha Harbor, 9-10a / More Info

• 🏃 32nd Annual MV Memorial Road Race at Summercamp Hotel, Oak Bluffs, 10a-12p / More Info / $30

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

• 💄 Time to Celebrate Pop-Up at Shades and Textures Salon (2 Pheasant Lane), Oak Bluffs, 2-5p / More Info
  Celebrate the new salon with beauty, shopping, sips, snacks, and local pop-ups from Shades and Textures Salon, Cinnamon White Beauty, and Andrea’s Brew MV.

• 🎶 Gordon Sunday Blues at VFW 9261, Oak Bluffs, 4:30-6:30p / More Info

• 🎶 Sundays In The Park Concerts at Ocean Park, Oak Bluffs, 5:30-7:30p / More Info

• 🎬 MVEFF: Time and Water at MV Film Society, 7:30p / More Info

Monday, May 25, 2026 - Memorial Day

• 🇺🇸 Memorial Day Picnic at Tashmoo Spring Park, Vineyard Haven, 12-4p / More Info / Free
  Celebrate Memorial Day with boating, music, children’s games, grilling, chalk art, and community fun at Tashmoo Spring Park.

  We remember, with gratitude, those who served and sacrificed for our country.

Read more

This list highlights creators who actually live on Martha’s Vineyard, visit often, or simply bring you the beauty or reality of MV living. They’re not all influencers, but are all creators or large-scale MV accounts with followings. If you’re looking to see the island through a more real, interesting, or inspiring lens, they’re worth a follow.

This list was pulled together in May 2026, and additions will be made periodically.

Island Influencers & Creators

Year-Round

• Marnely Murray ~12K (IG) chef & food writer sharing MV dining tips.

• TheRealEdgartown ~7k (IG) aesthetic island landscapes

• MVacay ~10k (IG) MV-focused local travel guides

• Mavi DeO ~14K (IG) lifestyle content with a Type 1 diabetes focus.

• Talita DeStefani ~28K (IG) Brazilian hair stylist + studio owner

• Abbie Schuster (17k IG) Kismet Outfitters owner

• Sarah Waldman ~12K (IG) year-round resident, cookbook author

• Vineyard Baker – ~24K (IG) home baker posting pastries and island life.

Seasonal Resident

• Baggage Girls ~13K (IG+TT) Two sisters focusing on sustainable travel

• Jenna DiMaggio ~13k (IG) seasonal resident + style and books

• Kara Roselle Smith ~80K (IG) Afro‑Indigenous educator highlighting Wampanoag history, based in NY

• AJ Calloway ~286K (IG) - seasonal resident

• Tyla Dacey ~23K (TT) - seasonal resident + creator

Annual Visitor

• Phoebe Lapine ~45k (IG) cookbook author, annual visitor

• Emma Lovewell ~734k (IG) Peloton Instructor, annual visitor

• Maddy DeVita ~608k (IG + TT) Hand me the Fork Private Chef Substack Author, annual visitor

• Toni Tanner Scott ~75k (IG) travel and 50+ lifestyle, visitor

• Crispin Haskins ~7k (IG) annual visitor, MV novel author

• Erin Goldson ~12k (IG) founder of Vineyard Icon, annual visitor

Tourism & Official Accounts

• Visit Martha’s Vineyard – ~43K (IG) official tourism board featuring events and sights.

• Visit Edgartown – ~18K (IG) guides to dining, shopping and activities.

• MV Chamber ~11K (IG) supports local businesses and event.

• MV Restaurants Guide ~3K (IG) - showcases island eateries.

• Vineyard Gazette & MV Times – local news outlets.

• MVY Radio – non‑profit radio station.

• Vineyard Transit Authority – public bus system.

• MV Land Bank – manages trails and conservation lands.

Hotels & Resorts

• Harbor View Hotel – ~28K (IG) waterfront luxury in Edgartown.

• Winnetu Oceanside Resort – ~17K (IG) family‑friendly resort.

• Point B Realty ~4K (IG) - real estate agency

Restaurants & Food

• Back Door Donuts – ~22K (IG) late‑night donuts in Oak Bluffs.

• Morning Glory Farm – ~23.6K (IG) farm stand & bakery.

Shops & Boutiques

• Vineyard Vines

• Black Dog

• Island Outfitters Oak Bluffs

• Toteally Yours MV

Arts & Non‑Profits

• Featherstone Center for the Arts – year‑round art center with a mission to “engage, enrich and connect” the community

• Martha’s Vineyard Museum – history & culture museum.

• Camp Jabberwocky – camp for people with disabilities.

• The Farm Institute – sustainable agriculture education.

• Vineyard Preservation Trust – restores and maintains historic buildings.

• Island Alpaca Company – farm tours & alpaca products.

• MV Sharks – collegiate baseball team.

Marketing + Creative Agencies with Clients on MV

• Shored Up Digital

• The Vineyard Bridge

• Cape & Vine

• Tyla’s Studio

• Baggage Girls

Disclaimer: this is a non-exhaustive list. Of course, there are tons of other influencers who visit annually you can follow. This is just my personal list and it is in no means meant to be a guide to all Creators on MV. If you have an inquiry or would like to be added please send me an email at info@mvacay.com 💜

⏱️ This Week on MVacay

I updated the Farmers Market Guide with 2026 dates! The season starts MDW:

I wrote my personal bucket list for the summer, and made a big list of what I need to do to prepare:

🗺️ What To Do This Weekend

Friday, May 15, 2026

• 💪 EFF’n Move Series with Tuni at Stillpoint, 9-10a / More Info / Free
  Free introductory mindful movement class blending yoga, barre, resistance bands, and functional fitness; all levels welcome.

• 🎸 Johnny Hoy and the Bluefish at the PA Club, 8p / $10 cover

Saturday, May 16, 2026

• 🌿 Annual MV Woody Plant Pest and Disease Update at Polly Hill Arboretum, 10a-12:30p / More Info / $75

• 🧹 Spring Clean Up Day at Agricultural Hall, 10a-1p / More Info / Free

• 🚶 Walk for Dementia and Caregiver Services at Nomans, 10a-1:30p (Rain date Sun) / More Info / $30 suggested donation
  Walk to Jaws Bridge and back or cheer from the sidelines, followed by live music and discounted food for registered walkers.

• 🧵 Craft Supplies Giveaway at Oak Bluffs Public Library, 11a-3p / More Info /
  Free fabric and craft supply swap with donations optional; bring your own bags.

• 🎶 Porchfest Edgartown throughout Edgartown, 1-6p (Rain date Sun) / More Info / Free
  Community-wide live music festival featuring bands performing on porches and patios around downtown Edgartown.

  • 1p — Phil & Moe at 19 Raw, DJ Smooth B at MV Boys & Girls Club, Red Night Delight at Edgartown Library, Offshore Blues at Eisenhauer Gallery, Rachel Elion Baird at Sea Spa Salon, Jim & Larry at Hob Knob, Agreeable Men at Town Bar & Grill

  • 2p — Darby & Sam at Bad Martha’s and Donaroma’s, Mike Benjamin & Jodie Treloar Sampson at Edgartown Inn, Beacon of Hope at Federated Church, Paul Thurlow’s Sparkestra at Vintage W&S

  • 3p — Zea May & Friends at Edgartown Books, Sarah Shaw Dawson & Friends at Eisenhauer Gallery, Coven at Hob Knob, The Ostinato Duo at Rosewater Market, Rose Guerin at Kenworthy, Phil & Moe at Kismet, Blue Yonder at Salte

  • 4p — Jim & Larry at Bad Martha’s/Donaroma’s, Sean McMahon & Agreeable Men at Rainy Day, Michael Haydn at Sea Spa Salon

  • 5p — Dave Willis and the Down Island Band at Edgartown Books, Phil DaRosa Band at Eisenhauer Gallery

  • 6p — Dock Dance at Memorial Wharf

• 🎻 Mike Block Trio at The Strand Theatre, 7-8:30p / More Info / $20

Sunday, May 17, 2026

• 🌱 Plant Sale at Milkweed Farm (with Merry Farm), 9a-4p (Sat & Sun)

• 🛍️ Spring Tag Sale at the parking lot behind Lani Beach Club, 11a-4p / More Info
  Shop spring fashion and lifestyle finds from Lani Beach Club, Trust the Shop, and Conrado during this pop-up outdoor tag sale.

• 🌿 The Giving Garden: Spring Tour, Taste, and Take-Home with Roxanne Kapitan at MV Public Charter School, 1-2:30p / More Info / Free

• 🏺 Ceramic Flower Vase Workshop at Featherstone Center for the Arts, 2-4p / More Info / $50

Read more

1. The practical prep and logistics I need to do NOW to enjoy summer

2. My family’s bucket list that includes local traditions, little things I don’t want to forget, and a few new experiences I want to prioritize this year.

Hopefully today’s picks give you a few ideas for your own lists, too!

This is NOT a 101 bucket list for first-time visitors. It’s a list of how I’m preparing for Summer, and things I hope to try for the first time!

📝 My Summer Prep List

1. 📅 Look Through the Events Calendar: Put dates on my calendar that I don’t want to miss, and grab tickets now.

2. 🕷 Tick Prevention Reset: Schedule yard spraying, restock Insect Shield permethrin-treated socks / spray (also available at Green Room), grab more NatPat patches and bug spray (also at Alleys).

3. 🎒 Sign the Kids Up for Summer Camps

4. 🥕 Eating Local: Decide whether we’re committing to a CSA this year, and make a list of pantry staples to supplement that during a big off-island Costco/Aldi haul. We’re leaning towards the Fisherman’s Trust CSF and Ghost Island Farm options.

5. 🏖 Beach Gear Refresh: Replace the sand toys that disappeared, buy more SPF for the kids and myself, towel cover ups, rock painting supplies, upgrade the beach bag situation. On-island options: we love Green Room for Yeti products, Island Outfitters OB for sunscreen, and Alleys for beach toys and insect repellent.

6. 👯‍♀️ Arrange Summer Visitors: Send everyone who’s visiting us the 2026 Visitors Guide and updated ferry info.

7. 📸 Set a Date for Family Photos: Our photographer books up quickly, so I emailed to arrange a session, and I already bought outfits.

8. 🚲 Locals Prep: Arrange bike tune-ups (size up in helmets too), buy beach stickers, do a cooler cleanout, reorganize the beach bin in the garage, power wash the furniture…all the glamorous seasonal tasks.

9. 🌧 Rainy Day Backup Plans: Restock puzzles, baking supplies, craft kits, sticker books, and save a few indoor activities before we inevitably get three rainy weekends in a row. Chicken Alley, Rainy Day and Bunch of Grapes are great on-island options for these supplies.

10. 🪣 Make a Family Bucket List: Make a big poster with my kiddos’ input of what THEY want to do this summer too!

🌿 Our Family’s Bucket List

🍳 Take a Cooking Class

I love any activity that ends in a meal and a new skill, this year I hope to try a cooking class at Slough Farm (they sell out immediately!) or go back to my favorite FARM Institute teachers.

🧵 Take a Craft Class

MV is fullll of creatives. I’m excited to take a needlepoint class this summer at The Stitchery and a glassblowing class at MV Glassworks. Past summers I’ve enjoyed offerings from Featherstone and library groups.

📚 Go to a Book Talk or Film Screening

I spent my winter reading MV authors Belle Burden and Emma Brodie, so I’m hoping to catch them speaking this summer. The MV Book Festival, MV Black Book Festival, Featherstone, Islanders Write and Edgartown Books have awesome lineups every year too. Another repeat tradition for me is the MVAAFF - I’m eager to see the panel lineup each year.

🎶 Go to More Live Music

The Tabernacle, The Grange, First Fridays, and Vineyard Sound concerts are summer staples. I’m also keeping an eye on Circuit Arts and Inkwell Beach House’s new programming. An updated live music guide is publishing soon as more dates trickle in.

🌸 Do Something Nature-y - Flowers, Hike or Bike

I saw the cutest idea to schedule a flower party at Slip Away Farm. For hiking, I always end up repeating my favorites, but I want to intentionally try at least one I’ve never done before. Squibnocket Pond Reservation (Aquinnah estate of former first lady Jacqueline Kennedy Onassis, aka Red Gate Farm) is on my list, as is the newly opened Mumcheag Creek Preserve on Chappaquiddick with views over Poucha Pond. Speaking of, I can’t wait to do a Chappy bike ride, it’s been a few years!

⛴ On the Water

Can I admit I’ve never taken a day trip to ACK?! I’m planning one this year! This is also the last summer of the Shenandoah in our harbor, so I’m thinking a boat ride is in order (especially with Cottage City’s new boat).

📍 Get Up-Island More Often

Obviously there will be many Menemsha sunsets and Galley ice cream runs, but I need to make a point to go up island more often this summer.

🛍 Shop Local Markets

I love to see the new vendors at the Artisan’s Market, Open Market, Chilmark Flea, farmers markets and roadside stands each year…especially for Father’s Day gifts or host gifts.

👨‍👩‍👧‍👦 Family Summer Traditions

We can’t go a summer without going to a Martha’s Vineyard Sharks Game, doing a Misty Meadows Pony Ride, and riding the Carousel. I think this year we’ll add in the Pirate ship and Ryan’s arcade for the first time.

🆕 New Business Tour

And of course, try all the new restaurants that open up! And support all the businesses in their first year of business. I’m especially excited about Highlands, Jetty Beach House, Bee Blunt and Biscuit by the Sea.

⏱️ This Week on MVacay

One of my favorite things to ask for Mother’s Day is family photos! We just scheduled ours, and it reminded me of this wonderful guide:

I also found myself referencing this inclusive list of wellness providers, which is a great place to go to find a gift card for mom:

🗺️ What To Do This Weekend

Friday, May 8, 2026

• 🎨 A Season of Flowers Opening Reception at Miner Family Gallery, 5-8p / More Info
  A floral-inspired collaborative art show by Taylor Stone and her mother Lori Stone opens Mother’s Day weekend.

• 🎉 Vineyard Montessori School’s Big Night Out at Portuguese-American Club, 7-10p / More Info / Free
  A lively annual fundraiser with music, dancing, food, and an online auction supporting local education.

• 😂 An Evening of Comedy with Susan Rice at The Strand Theatre, 7:30p / More Info / $45

Saturday, May 9, 2026

• 🌱 Community Greenhouse Annual Sale at Community Greenhouse of Martha’s Vineyard, 10a-3p / More Info

• 🌿 Tyke Hikes at Felix Neck Wildlife Sanctuary, 9:30-10:30a / More Info

• 🛍️ Mother’s Day Market & Brunch Specials at Town Bar & Grill MV, Sat 12-3p / More Info
  Enjoy Mother’s Day specials while shopping a pop-up market featuring 14 local artists and makers. Specials available Sunday for Brunch too.

• 🌱 Seedlings By The Sea at West Tisbury Free Public Library, 2-3:30p / More Info
  Kids in grades K–8 can decorate pots, plant sprouts, and enjoy snacks at this hands-on community event.

• 🥣 Empty Bowls Fundraiser Supper & Silent Auction at The Grange Hall, 5-9:30p / More Info / $35-$60 suggested donation
  An evening of dinner, music, dancing, and a silent auction benefiting children and families in Gaza.

• 🎭 No Bones Variety Show at Martha’s Vineyard Playhouse, 6p + 8:15p / More Info / Pay-what-you-can
  An eclectic comedy showcase featuring improv, sketch, and experimental performances.

• 🎶 Minnesingers Spring Concert at MV PAC, 7-8:30p / More Info / $5–$15

Sunday, May 10, 2026

• 🌸 Mother’s Day Brunches & Specials

  • Brunch & Mini Family Portraits at Harbor View Hotel, 11a-3p

  • Open for Brunch at Lambert’s Cove Inn, Red Cat Kitchen, Maker Cafe, Rockfish, Pawnee House and 19 Raw Oyster. Sweet Life is sold out.

  • High Tea at S&S Kitchenette, 1-4p

  • Portrait Pop-Up at Morrice Florist, starts around 11a

• 🎬 The Devil Wears Prada 2 at Edgartown Cinemas, 1p & 6:30p

• 😂 An Evening of Comedy with Ophira Eisenberg at The Strand Theatre, 7p / More Info / $45

Read more

⏱️ This Week on MVacay

For annual visitors, this checklist is helpful to plan your trip. It rounds up all the links you need in one place:

And for those looking for Mother’s Day and Father’s Day gifts, this is a wonderful resource:

🗺️ What To Do This Weekend

Friday, May 1, 2026

• 🎨 May Day: Plant, Paint, Play Workshop at MV Museum, 3–4:30p / More Info / $25

• 🎶 Trio Eris Concert at Edgartown Public Library, 3–4p / More Info

• 🎉 Dine to Donate Fundraiser at Vineyard Grill (5 Corners, VH), 6–9p / More Info
  Enjoy live music, raffles, and food while supporting Visit VH and local arts initiatives.

• 🎭 Locals: A Two-Night Festival of Vineyard Talent at MV Playhouse, 7p (Sat too) / More Info / pay-what-you-can
  This two-night community festival showcases local performers across music, theater, dance, and spoken word.

• 🎶 Meredith Sheldon + Wolftrap at S&S Kitchenette, 7p

• 🎸 Paleface and Mo Live in Oak Bluffs at PA Club, 7–9p / More Info / $10

• 🎧 Weekend Vibes with DJ Smooth B at Indigo Restaurant (Sat too), 10p

Saturday, May 2, 2026

• 🚴 Bike MS: Ride the Vineyard 2026 at MVRHS, 7:30a–3:30p / More Info

• 🌿 Tyke Hikes at Felix Neck Wildlife Sanctuary, 9:30–10:30a

• 🌸 Maypole Celebration at West Tisbury Public Library, 11a / More Info

• 🏇 Kentucky Derby Day at Town MV at Town (Edgartown), all day

• 💼 Career Navigation Office Hours with AceMV at WT Library, 3–4p / free

• 🛋️ Grand Opening at Summer Street Upholstery, 5–7p (Sun too) / More Info

• 🎵 Blues Duo at The Pawnee House Restaurant, 6–8p

Sunday, May 3, 2026

• 🚶 Land Bank Natural History Walk at Tea Lane Farm, 9–10:30a / More Info / free

• 🐐 4-H Farm Animal Meet and Greet at Ag Hall, 10a–12p / More Info / $5

• 🌱 Gardening 101 at West Tisbury Public Library, 1–2:30p / More Info / free

• 📸 Mother’s Day Portraits at West Tisbury Public Library, 1–3p / More Info / free

• 📰 Publisher’s Forum: World Press Freedom Day at MV Times Office, 4–6p

• 🌸 The Art of Flowers: Creativity in Bloom Opening Reception at Featherstone Center for the Arts, 4–6p / More Info / free

Read more

⏱️ This Week on MVacay

🗺️ What To Do This Weekend

Friday, April 24, 2026

• 🌳 Arbor Day Celebration at Polly Hill Arboretum, 1-2p / More Info / Free
  Guided tour of notable trees followed by a live tree planting demo; meet at the Visitor Center and no registration required.

Saturday, April 25, 2026

• 🌿 Seasonal Staff-Led Tours at Polly Hill Arboretum, 10-11a / More Info / $5

• 🐴 Spring Vacation Pony Rides at Misty Meadows Equine Learning Center, 10a-12p / More Info / $30
  15-minute pony rides for kids on a scenic farm; advance booking required.

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

• 🎨 Shibori Dyeing with Indigo Workshop at Featherstone Center for the Arts, 1-4p / More Info / $80

• 📚 Book Signing: Into The Blue by Emma Brodie at Edgartown Books, 2-4p / More Info / Free
  Meet the author and celebrate Independent Bookstore Day with a signing of her latest novel.

• 🗣️ Weaving Generations: A Multi-Generational Forum on Conflicts in Workplaces at Oak Bluffs Public Library, 2-4p / More Info / Free

Sunday, April 26, 2026

• 🏃 MV Spring Classic Marathon & Half Marathon at Martha’s Vineyard Regional High School, 8a-2p / More Info / $120

• 🦙 2026 Annual Shearing Day Celebration at Island Alpaca, 10a-4p / More Info / $8
  Family-friendly day watching alpacas being sheared, with demos, raffles, and food available on-site.

• 🎬 The Princess Bride — Free, Interactive Film at Martha’s Vineyard Film Center, 11a / More Info / Free
  Family-friendly interactive screening of the classic film; reserve tickets in advance and arrive 30 minutes early.

• ☕ Cup of Karma Cafe at Stillpoint, 2-3:30p / More Info / $10

• 🎶 Rose Coloured Glasses Concert at West Tisbury Public Library, 2p / More Info

Read more

This is what I’ve gathered so far, and I’ll keep updating the web version as more additions roll in throughout the season.

🍽️ New Businesses

🍴New Restaurants or Food Offerings

Highlands Market (OB) – New café-marketplace now open in the former Linda Jean’s space, with breakfast and lunch offerings from the team behind Nancy’s and Nomans.

Toccopuro (VH) – Mocha Mott’s property sold to the Toccopuro group; a new restaurant or café concept is expected to replace the Vineyard Haven location. Mocha Mott’s remains open in Oak Bluffs.

The Wave Restaurant + Bar (VH) – New restaurant replacing Garde East at Vineyard Haven Marina for the 2026 season.

Jetty Beach House (OB) – New raw bar and cocktail concept planned for the former Lobsterville space from the team behind Midnight Taco, targeting a Memorial Day opening

Inkwell Beach House (OB) - Opening May 2026 in the former Chowder Company space as a restaurant and large-scale event venue, with a concept led by AJ Calloway and a restaurant from celebrity chef G. Garvin.

Coastwise Pub (OB) - Opening in the former Mikado Oak Bluffs space, and by the owners of Black Dog, they will serve breakfast, lunch, dinner, coffee, and cocktails planned. Opening date TBD.

🛍️ New Shops

Biscuit by the Sea (Edg) – Home décor shop opening a new location at 41 Main Street.

Sweetish Fish (Edg) – Candy shop expected to open a new Edgartown location, on 1 S Water Street.

Bee Blunt (VH) – Clothing and lifestyle shop expanding after several years of pop-ups in Oak Bluffs, located in the former Old Stone Bank Conrado space.

Alex Mill (Edg) - Alex Mill (former head of J.Crew) will open in the former Suka space in Edgartown. TBD.

Oleanna (VH)- a women’s clothing, jewelry and homegoods store will open in the former Magnetic North location in Vineyard Haven.

Lexie’s Rack – Vintage clothing and curated finds ONLINE shop launching soon

Kismet Outfitters – Planning a second location expansion, TBD.

MIIO: Made in Italy Only (VH) MIIO is opening in the former Adrift space in Vineyard Haven, bringing luxury goods made in Italy to its first MV storefront after several years as a Chilmark Flea vendor.

💆 Wellness Services and Experiences

Harbor & Hive – Organic yard care service offering tick, mosquito, and deer deterrent treatments.

Luminous Mind Hypnotherapy – New hypnotherapy offering focused on habits, anxiety, and personal development.

The Remembrance Studio – Grief coaching and memorial planning service offering custom tributes, gatherings, and memory-focused experiences.

The Collected Table MV – Event styling service offering curated tablescapes for intimate gatherings and celebrations.

The Stitchery MV (VH) - Studio offering small group needlework classes and private hand-sewing lessons from an experienced teacher

Inner Sanctuary MV – Yoga offering focused on private sessions, group classes, and event-based wellness experiences

Good Days Ahead Wellness House – New immersive wellness experience launching August 17–19 with multi-day programming and community-focused events

MV Mahjong - New private lesson option for beginners learning Mahjong, certified by Oh My Mahjong

🔄 Expansions, Ownership Changes + Movement

🤝 New Owners or Management

Steere the Course Mini Golf & Grille: The former Cove Mini Golf location at 386 State Road in Vineyard Haven appears to have a new name and ownership

Plane View Restaurant (MV Airport) – Reopened under new ownership

Vineyard Grill (VH) – Formerly MV Tap, now under new ownership with a revised restaurant concept at Five Corners.

ESH (OB) – Newly opened in the former Dos Mas space on Circuit Ave following a renovation and updated concept.

MV Family Campground (VH) – Acquired by national resort operator Northgate Resorts, marking a major ownership change after decades of family ownership; no immediate changes are planned for the 2026 season.

Future General Store planned for the Sole building in Edgartown, expected in 2027

Offshore Ale (OB) potentially will expand into Notalot Farm Stand space in 2027.

Square Rigger (Edg) – Reopened under new ownership by Abraham and Brian Torres

Roy’s Oyster Operation (Katama Bay) – Now operated by Martha Scheffer, continuing the long-standing family oyster business under new leadership

Pie Chicks on Break: Pie Chicks will be on sabbatical through Thanksgiving, and not operating out of the Vineyard Haven location this summer.

Yommi Pops Brick and Mortar: Yommi Pops will take over the former Pie Chicks location this season, at 395 State Road in Vineyard Haven.

Mad Max Sailing: Mad Max is closed for the 2026 season, with “the new” Mad Max II coming in 2027/2028.

The Chappy Ferry has new ownership this year.

📦 Moving

Frankie’s Revival (VH → OB) – Now open on Circuit Ave with thrift and vintage finds.

MV Chowder Company (OB) – Closed its previous location and planning a move to a new 14 Ave Kennebec Ave space. Opening timeline TBD.

Benito’s Hairstyling (OB → Edg) – Relocated to Gypsy Barbershop in Edgartown.

Conrado (VH) - Has condensed to one space (the Old Stone Bank property that sold gifts will merge into 2 Union Street)

🏗️ Other Island Changes

🛠️ Renovations + Evolving Infrastructure

Vineyard Haven Library – Closed for full renovation, operating out of temporary space at 15 Church Street.

MV Airport Terminal Project – Moving forward with federal funding; construction continues into 2026.

SSA Woods Hole Terminal – Reconstruction ongoing, expected completion around Memorial Day 2026.

Gay Head Cliffs Stairway (Aquinnah) – Reconstruction underway to improve ADA accessibility and access to shops; expected completion this spring.

Vineyard Wind – Offshore construction officially completed, marking a major milestone for the 62-turbine project.

Philips Hardware Site (OB) – Demolition underway ahead of redevelopment into a mixed-use building with housing and retail.

YMCA (MV) – Operating out of the Ice Arena during ongoing construction.

Harbor Homes – Secured a permanent Vineyard Haven location at 515 Edgartown-Vineyard Haven Road, expanding its year-round shelter presence.

Ocean View Hotel (OB) – Project approved by MVC; development plans continue to evolve.

Island Theatre (OB) – Oak Bluffs voters approved funding to pursue acquisition of the long-vacant theater property as the town explores future plans for the site.

Union Chapel (OB) - Renovation currently underway for improved accessibility circulation.

Meshacket Commons (Edg) – New affordable year-round housing development in active rollout on Meshacket Road; rental and ownership applications have closed as the 40-home project moves toward its 2026 opening.

Oak Bluffs Bandstand - currently undergoing ongoing maintenance

REGENT Seagliders: REGENT shared a Providence-to-Martha’s Vineyard seaglider route graphic with an estimated 35-minute port-to-port travel time.

📅 New Events + Venues

First Ferry Party (OB) – New annual kickoff event planned for May 14, 2026 to celebrate the start of the season.

InkWellness Fest – New wellness-focused festival concept with a community event planned near Inkwell Beach August 5, 2026.

Oak Bluffs Tennis Club – Revival efforts underway to bring back the historic club with its first Labor Day tennis tournament and June clinic as a partnership with East Chop Tennis Club.

HBCU Arts Festival - HBCU student performers visiting the week of 8/1–8/6

Mass250 - Special for 2026, MA is celebrating 250 years of independence, and MV played a small role in it. There will be special programing all summer.

MV SOUND Returns: Martha’s Vineyard SOUND announced its weekly Thursday concert series returning to The Strand Theatre from 5/14–6/25.

JAWS: On Amity Island: The Chamber announced a July 11 “Float in the Dark” screening of Jaws at Owen Park in Tisbury. They’re also hosting a MV Culinary Classic debuting October 15–18, 2026.

Circuit Arts Live Music Series: Circuit Arts and MVYRadio are launching a new year-round live music series with performances at The Strand Theatre, Martha’s Vineyard Playhouse, The Grange Hall, and The Old Whaling Church.

MV Agricultural Society Farm Day: The first annual Farm Day is Friday, June 26, with free tours 8+ island farms.

🎨 New Groups + Media

Theatre on the Blue – New nonprofit focused on accessible theater programming.

Tick Free MV – New nonprofit launched to address tick-borne illness through deer population reduction efforts, research, and public education.

MV Tick Center - A new Tick Center is set to open next month through Martha’s Vineyard Medical, offering coordinated care for Lyme, alpha-gal, and other tick-borne illnesses

The Vineyard Bridge – Brazilian-owned business accelerator and consulting platform.

NOEPE Studio – Production studio offering podcasting, AI content, and media services.

Midnight Land Collective – Wampanoag-led conservation organization focused on land stewardship and cultural revitalization.

Oak Bluffs Economic Development Efforts – Town-led initiative addressing storefront vacancies and year-round business activity on Circuit Ave.

The Buzz MV – New seasonal digital and print publication launching for Summer 2026, focused on Island culture, events, and local features

👋 Goodbye (for now) to…

MV Streetwear + Sideline, Slip77, Mocha Mott’s (VH), Adrift (VH), Garde East (VH), The Loft, Mikado (OB), Tisbury Ice Box, Magnetic North, Ice Box, Suka,

Thanks for supporting local! I’ll keep this list growing all spring. Check back for updates 🙌

⏱️ This Week on MVacay

With Spring Break coming up this week it reminded me of some of my favorite family-friendly guides!

Buy the Family Guide PDF on Etsy for $10

🗺️ What To Do This Weekend

Friday, April 17, 2026

• 🦪 The Bivalve Ball - Tickets SOLD OUT

• 🎬 Best of the Fest Film Series at the Grange Hall, starting 5p / Tickets

  • Everybody to Kenmure Street, 5p Fri

  • When a Witness Recants, 7:30p Fri

  • Nuisance Bear, 5p (Sat)

  • The Christophers, 7:30p (Sat)

Saturday, April 18, 2026

• 🏠 Estate Sale – Second Treasures MV at 24 Beetleswamp Rd, Edgartown, 10a-2p (Sun too) / More Info
  A multi-day estate sale with a broad mix of household goods, vintage finds, and assorted treasures.

• 🌱 34th Annual Earth Day Beach Cleanup and Conservation Festival at Martha’s Vineyard Museum, 10a-3p / More Info / Free
  A community-wide Earth Day tradition that pairs a large Island beach cleanup with an afternoon conservation festival.

• 👕 Clothing Swap at Oak Bluffs Public Library, 11a-3p / More Info / Free
  This free community swap welcomes all ages and sizes for an afternoon of sharing gently used clothing.

• 🌸 Orchid Class with Mariko and Grace at Donaroma’s Nursery, 1-3p / More Info / $95
  An orchid-focused workshop covers care, styling, and re-blooming, and each participant takes home a plant.

• 🎨 Significant Objects Memory Collages Workshops at Featherstone Center for the Arts, 1-3p / More Info / $50
  Personal memories take shape in this guided mixed-media workshop led by two local artists.

Sunday, April 19, 2026

• 🎬 National Theatre Live – The Audience at MV Film Center, 1p / More Info

• 🎶 Music Series: Mike Benjamin and Friends at PathwaysARTS, 3-4:30p / More Info / Free
  A relaxed Sunday matinee brings together four songwriters for an acoustic in-the-round performance.

Spring Break Weekday Highlights

• 4/21-24 - Free Soup & Bread Lunch @ West Tisbury Library, Tues-Fri (11:30a-1p)

• 4/21 - Make Your Own Charm Bracelet @ OB Library, 3:30p

• 4/22 - The Wild World of Animals Show @ Tisbury School, 3:30p

• 4/23 - Pancakes and Cartoons @ West Tisbury Library, 9:30a

Read more

🗓️ Daily Schedule

Wednesday, June 10, 2026

• 🍿 LGBTQ Movie Night @ The Pawnee House, 7:30p / Tickets
  Watch Pride, Reservation required, 4 courses + snacks, $75 per person

Friday, June 12, 2026

• 🎟️ Emily King @ The Strand Theatre, 8p / Tickets

  Grab tickets to see her live in concert with Circuit Arts

• 🎉 Pride Party Kickoff @ The Ritz Café, 8p
  Start the weekend with a high-energy celebration including drag queens, swag, a glitter bar and everything you need to know about Pride!

Saturday, June 13, 2026

• 📕 9:30 AM - Drag King Storytime @ West Tisbury Public Library

  Join for books that celebrate difference + embrace diversity with Benjamin Clover

• 🎉 1 PM - Pride Parade Pregame @ The Ritz Café

• 🛳️ 2 PM – Parade Lineup Begins @ Island Queen Ferry Terminal

  • Marchers and floats should arrive at the Oak Bluffs Harbor by 2 PM to line up. The parade will step off from this location at 3 PM sharp.

• 🎉 3 PM – Parade Begins @ Island Queen Ferry Terminal

  • March from the ferry along Seaview Ave, Circuit Ave, Narragansett Ave, and Niantic Ave, ending in Ocean Park.

• 🎶 4–6 PM – Music + Community Organizations @ Ocean Park

  • Tent is sponsored by QueerHubMV and MV Community Services.

  • The Femmes Band and Lexastential Crisis at the Ocean Park Gazebo.

  • Vineyard Social Booth photo op

• 🍹 4-6 PM – Pride Happy Hour @ The Ritz

  • Half off Burgers + other food specials, with music too! Pocket Dogs

• 🕺 9 PM – Late Night Dancing @ The Ritz

  • Celebrate with DJs, dancing, games, swag, and more.

  • DJ SKKRRT at 10pm

Sunday, June 14, 2026

• 🍳 Drag Brunch @ Black Joy Kitchen, 11a + 2p seatings / Tickets

  • With returning Queen Mizery and friends

🌈 Pride Weekend Essentials

🥇 Silent Auction

Support Pride - our 2026 silent online auction is coming Friday!

📍 Parade Route

The parade kicks off at the Island Queen Ferry terminal and winds through downtown Oak Bluffs via Seaview Ave, Oak Bluffs Ave, Circuit Ave, Narragansett Ave, Niantic Ave and ending in Ocean Park.

🛠️ Community Resources

Stop by the MV Community Services tent to connect with island nonprofits offering support, information, and giveaways.

🚗 Parking Info

First come, first served. Best options include: Washington Park, East Chop Beach Club overflow lot, Niantic Park area side streets. Parking fills fast—carpool, bike, or bus if possible!

🚻 Restrooms

Public bathrooms available at: Kennebec Ave (across from Aalia’s), Harbor area (by Winston’s), Steamship Authority Ferry Terminal (brick building near vehicle exit), Oak Bluffs Public Library (limited hours).

🛳️ Day-Tripper Tips

Coming just for the day? Make sure your ferry destination is Oak Bluffs, not Vineyard Haven, for the most convenient access to the parade and Ocean Park events. Go to the Visitors Booth for information, and ride the VTA bus free from Vineyard Haven if you need. Need help with planning your trip? Email us at marthasvineyardpride@gmail.com and we can help!

🤝 Sponsors!

Thank you to our sponsors and donors:

Become a Pride Sponsor!

⏱️ This Week on MVacay

This week I’ve been hard at work on the New Businesses for 2026 Guide! Got a hot tip on anything new or changing? My DMs and inbox are OPEN! For now, during my little research hiatus, here are two wonderfully relevant guides:

🗺️ What To Do This Weekend

Friday, April 10, 2026

• 🎲 Friday Game Time at the Museum at MV Museum, 1-4p More Info / free entry

• 🎭 Once Upon A Starry Night Play at Katharine Cornell Theater, 7p More Info / $5

• 🎶 The Big Kids / Outskirts at PathwaysARTS, 7p / More Info

Saturday, April 11, 2026

• 🏥 Martha’s Vineyard Hospital Community Health Fair at Martha’s Vineyard Hospital, 8a-12p More Info / free
  A community wellness event offering free screenings, health resources, and expert talks on topics like tick-borne illness.

• ⚓ Boatyard Shop Talk at Gannon & Benjamin Marine Railway, 9:30a More Info
  A behind-the-scenes look at winter boatyard projects with coffee, muffins, and conversation about wooden boatbuilding.

• 🌾 Beach Grass Planting at Lobsterville Beach, 9a-12p More Info

• 🚶 Annual Sexual Assault Awareness Month Walk at Ocean Park gazebo, 9:45a registration, 10a walk (rain date: Sun) More Info

• 🎧 Living Soundtrack Workshop at Slough Farm, 10a More Info

• 🌿 Guided Walk at Mumcheag Creek Preserve(new on Chappy), 10a More Info
  A guided nature walk through a NEW scenic coastal preserve highlighting local ecology and conservation efforts.

• 🍞 Homemade English Muffins with Vineyard Baker at FARM Institute, 10a-12p More Info / $50, only a few tickets left

• 🍪 Spring Cookie Decorating at Oak Bluffs Public Library, 2:30-3:30p More Info / free, kid-friendly

• 🎉 Harmony and Heritage: a Night of Togetherness at PA Club, 6-9p / More Info / free entry, silent auction to support Island Children’s School

• 🎵 Island Community Chorus Spring Concert at Old Whaling Church, 7:30-8:30p (Sun too) More Info / $20 suggested donation

Sunday, April 12, 2026

• 🌸 Flower Workshop at S&S Kitchenette, 2p More Info / $38, with Morrice Florist

• 🎥 The Hand That Holds The Line at MV Film Center, 4p More Info / $15
  A documentary on Cape Cod fishermen, followed by a panel with filmmakers and local fisheries experts.

• 🎬 Project Hail Mary at Edgartown Cinemas, 6:30p More Info
  A high-stakes space survival story blending science, humor, and discovery.

Read more

⏱️ This Week on MVacay

I added about 50+ save the dates to my year-long list!

🗺️ What To Do This Weekend

Friday, April 3, 2026

• 🎉 Carnegie Heritage Center Opening Weekend at The Carnegie, 10a-4p (Sat too) / More Info / $5

• 🏀 Final Four Watch Party at Strand Theatre, 7-11p
  A big-screen doubleheader at the Strand turns Friday night into a full women’s semifinal watch party. 7p is South Carolina vs UConn and 9:30p is Texas vs UCLA. 6-10:30p on Saturday too.

• 🎤 5th Annual Lip Sync Contest at PA Club, 7-10p (Sat too) / $25
  A two-night event with doors opening at 6p, limited capacity (125 people), and tickets available in advance or at the door if space allows.

Saturday, April 4, 2026

• 🥚 Egg Hunts Today:

  • 🥚 Vineyard Confections Annual Spring Egg Hunt at Island-wide, 8a-12p

  • 🥚 Easter Egg Hunt and Egg Coloring at Village Green - St. Andrew’s Church, 9-10:30a / More Info

  • 🥚 Annual Farm Institute Egg Hunt at The FARM Institute, 9:45-10:30a / More Info / $10

  • 🥚 Misty Meadows Spring Egg Hunt at Misty Meadows Equine Learning Center, 10a-12p / $5

  • 🥚 Spring Party & Egg Hunt at Aquinnah Public Library, 12-3p

• 🌸 Spring Flower Class at Morrice Florist, 11a-4p / More Info / $100
  A reservation-based floral workshop runs in two Saturday time slots with mocktails and spring arrangements.

• 📚 Book Tasting Event — Read-A-Latte Cafe at Oak Bluffs Public Library, 11a-2p / More Info
  A drop-in library event features genre tables, light refreshments, and easy checkout for anyone with a card.

• 🎨 Block Printing Workshop at Featherstone Center for the Arts, 12-3p / More Info / $65
  A hands-on printmaking class in Oak Bluffs is best for anyone planning to stay for the full studio session.

Sunday, April 5, 2026

• ⛪ Easter Services at Menemsha Beach, Inkwell Beach, and Agricultural Hall, Menemsha Beach 6a, Inkwell Beach 6:15-6:45a, Agricultural Hall 10-11a

• 🥂 Easter Brunch Options at Maker Café, Alchemy, The Ocean Club, Black Joy Kitchen, Sweet Life Café, Harbor View Hotel 11a-3p

• 🥚 Chilmark Easter Egg Hunt at Chilmark Community Center, 10:30a

Read more

⏱️ This Week on MVacay

Every March I talk about planning bachelor and bachelorette parties! This year, I split my guides up into a specific guide for Edgartown and Oak Bluffs. I think they are the two best destinations for large groups, and there’s plenty to do without a car. Share with a friend who’s recently engaged! 💍

🗺️ What To Do This Weekend

Friday, March 27, 2026

• 🎬 26th Annual MV Film Festival @ The Grange Hall & MV Playhouse, Times vary (Fri–Sun) / More Info / pay-what-you-can
  A multi-day festival of screenings, Q&As, food, music, and community events split between Vineyard Haven and West Tisbury.

  • 🎥 Featured weekend titles include Mary Oliver: Saved by the Beauty of the World, Cookie Queens, Following Harry, The Christophers, Vineyard Shorts, and When a Witness Recants

  • 🎟️ All screenings are pay-what-you-can; box offices open one hour before the first screening each day

  • 🍽️ Grange Hall meals from Chef Nina Levin run $22–$27, with beer, wine, and concessions also available at both venues. Ticket and pass holders can get restaurant discounts around town, including 10–20% off at select spots during the festival weekend

  • 🎶 Festival meals and receptions include live sets from local musicians, with Playhouse and Grange Hall performances woven into the weekend schedule.

• 🌸 The Woman Among the Orchids @ MV Museum, 5-6p / More Info / $25
  A museum talk featuring Mariko Kawaguchi on her life, artistic path, and years cultivating beauty on MV.

• 🎶 Hoops and Music — College Basketball On The Big Screen @ The Strand Theatre, 7-10p / More Info
  Watch NCAA college basketball on the big screen in a theater setting with music, community energy, and a nightlife vibe.

Saturday, March 28, 2026

• 🛍️ Second Chapter: Home Goods and Appliance Swap @ Oak Bluffs Public Library, 10:30a-3:30p / More Info
  Bring clean, working household items to swap or simply browse for useful secondhand finds.

• 🥚 Spring Egg Hunt @ West Tisbury Public Library, 10:30-11a / More Info / free
  A free annual egg hunt outside the library followed by family crafts in the Children’s Room.

• 💇‍♀️ Daddy and Daughter Styling Class @ Sea Spa Salon, 12-2p / More Info / free

• 📣 No Kings Rally 3 @ Five Corners, 1:30-3p / free
  A community rally in Vineyard Haven inviting Islanders to gather in support of democracy and civic participation.

• 🎥 The Genius of Marian @ MV Film Center, 4p / free
  A free screening presented with the MV Center for Living, followed by a Q&A with filmmaker Banker White and a panel on dementia, caregiving, and aging.

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

• 🍲 Aquinnah Library Community Dinner @ Aquinnah Town Hall, 5:30-8p / More Info
  A potluck-style community dinner with soups and sandwiches provided plus live music from Rose Guerin, Buck Shank, and Lydia Fischer.

• 🎶 Gig for the Gigs (with Delanie Pickering & Friends, supporting Sail MV) @ P.A. Club, 7-10p / $20

• 🎸 BlueSwitch Blues Band and Composer Tony Tobia @ PathwaysARTS, 7-9p

Sunday, March 29, 2026

• 🎬 MVFF Screening: Vineyard Shorts @ MV Playhouse, 3:45p / More Info / pay-what-you-can
  A showcase of short films connected to MV, followed by a conversation with the directors.

• 🏀 Waylon Madison Sauer Memorial Basketball Tournament @ MVRHS, 10a
  A community tournament honoring Waylon Sauer with players, volunteers, and supporters gathering to benefit his scholarship fund and the Class of ’27.

Read more

🛬 Getting Here + Where to Stay

• Arrive via ferry into Oak Bluffs or Vineyard Haven, then take a quick bus or rideshare into Edgartown.

• You do not need a car if you’re staying in town.

• Stay near Main Street, North Water Street, or closer to the harbor for the easiest setup.

• Book early - Edgartown rentals and hotels fill quickly, especially for summer weekends.

✅ What to Book Before You Arrive

Edgartown requires a little more planning than Oak Bluffs, especially for dinner.

Pick 1 main activity and build Saturday around it:

Bring in house to your rental:

• MV Picnics — beach or backyard setup, best for a styled “main event” moment

• Social Coast Mobile Bar — comes to your house for a cocktail class, easy and fun pre-dinner

• Private Chef (On Time Catering) — easiest way to do a group dinner without coordinating reservations

Get out:

• Mad Max Sailing Adventure — right out of Edgartown harbor, great for groups and afternoon sails

• Farm Institute Cooking Class — email them to schedule a group activity or ice cream making class

• Beach day at South Beach (Katama)— short bike ride from town

Also:

• Make one dinner reservation (for Saturday)

• Schedule alcohol / grocery delivery via Ahead of Arrival

📆 3-Day Edgartown Bachelorette Itinerary

Friday: Arrive, Dinner, Go Out

• Afternoon: arrive, check in, get settled and ready.

• Pre-Dinner: Start with a walk down Main Street → North Water Street → Edgartown Lighthouse. Grab a drink at Pelican Club before dinner.

• Dinner: Seafood Shanty (best walk-in option for groups) or 19 Raw if you want to start stronger

• After Dinner: drinks and dancing at Port Hunter → The Wharf

Saturday: Main Event Day

• Brunch: Behind the Bookstore (sit-down, worth it). Spend the late morning shopping Main Street + walking the harbor.

• Main activity: Mad Max, South Beach at Katama, or a lighthouse picnic

• Afternoon: more shopping, coffee stop, or a quick reset at the house

• Pre-dinner drinks: Harbor View (Bettini, Behind the View porch)

• Dinner (pre-book this): The Covington

• After Dinner: Atlantic and then ice cream at Mad Martha’s

Sunday: Coffee, Walk, Leave

• Morning: Coffee from Toccopuro or brunch at Among the Flowers. Go for a long Katama loop walk or bike ride if you’re up early.

• Lunch: Bad Martha Farmer’s Brewery for some day-drinking, pizza and group goodbyes before the ferry

Subscribe now

💡 MVacay’s Edgartown Bachelorette Tips

Book your dinners early, restaurants are small so large groups are tricky. Plan your outfits around dinners and going out because Edgartown leans more dressed up. Everything is walkable, but spread out just enough that comfortable shoes help and you may even want to rent a bike.

🛬 Getting Here + Where to Stay

• Arrivals: arrive via ferry in Oak Bluffs. You’ll likely be in walking distance of where you’re staying from the ferry port.

• Cars: You do not need a car if you’re staying in town. You may need to ride share if you arrive via plane or decide to go to a different town.

• Where to Stay: Stay within walking distance of Circuit Ave, the harbor, or Ocean Park. A reminder that there are very few rentals for large groups, and many of them have 3 or 7 day minimums. So book early! Our preferred hotels are Summercamp, Oak Bluffs Inn, Morgan, or an AirBnB walkable to Circuit Ave.

✅ What to Book Before You Arrive

The advantage OB is that thee is a lot that accommodates walk-ins. However, to have a plan I suggest you pick 1–2 of these and build Saturday around it:

Bring in house to your rental:

• MV Picnics — beach or backyard setup, best for a styled “main event” moment

• Social Coast Mobile Bar — comes to your house for a cocktail class, easy and fun pre-dinner

• Private Chef (On Time Catering) — easiest way to do a group dinner without coordinating reservations

Get out:

• Toteally Yours Totes — personalize your own coastal tote bags with this in-store experience, ready same-day.

• Cottage City Charters — half-day or sunset charter boat (up to 6 people) with pick-up in Oak Bluffs harbor.

• Stefanie Wolf Charm Bar — customize or get permanent bracelets, pre-book for a group

Also:

• Make one dinner reservation (for Saturday)

• Schedule alcohol / grocery delivery via Ahead of Arrival

📆 3-Day Oak Bluffs Bachelorette Itinerary

Friday: Arrive, Dinner, Go Out

• Afternoon: arrive + check in. Get groceries + drinks. Get ready.

• Pre-Dinner: walk Gingerbread Cottages (MVCMA). Stop at Ocean Park for photos. Grab a drink at Nancy’s.

• Dinner: Lookout Tavern (lobster rolls, sushi, easy for groups) or Coop de Ville (more casual, fun vibe) Put your name in early and expect a wait — that’s normal here.

• Post-Dinner: go to The Ritz for live music + dancing. Then, get Back Door Donuts

Saturday: Main Event Day

• Morning: coffee at Aalia’s Coffee. Make beach sandwiches at home.

• Schedule an Excursion or Activity: MV Picnics setup + beach time (Inkwell or State Beach) or beach time at Inkwell.

• Afternoon: walk Circuit Ave + shop. Make totes at Toteally Yours or bracelets at Stefanie Wolf.

• Pre-Dinner: Nomans (drinks, lawn games, music)

• Dinner: Pawnee House (best overall group dinner vibe in OB), Sweet Life (more intimate, bougie, reservation-heavy) or Red Cat Kitchen (slightly outside main strip but worth it)

• Post-Dinner: The Alley again if the group wants to go out-out. Grab Gio’s pizza late-night.

Sunday: Coffee, Walk, Leave

• Morning: grab breakfast sandwiches from Tigerhawk, then walk up East Chop drive to see East Chop Lighthouse.

• Pre-Ferry: Check out of your AiBnB. Head to the Fishing Pier and sit and enjoy the sunshine! Check out the Flying Horses if you’d like.

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💡 MVacay’s Oak Bluffs Bachelorette Tips

Stay walkable. Book one activity and one dinner, and let the rest of the weekend stay flexible. Put your name in early at dinner spots, expect waits, and don’t try to over-engineer the schedule. Oak Bluffs works best when you lean into the energy instead of overplanning it!

⏱️ This Week on MVacay

🗺️ What To Do This Weekend

Friday, March 20, 2026

• 🎉 Edgartown Public Library’s 10th Anniversary Celebration at Edgartown Public Library, 3-4p / More Info
  Cake, conversation, and a chance to celebrate ten years of the town’s modern library with the staff, volunteers, donors, and community members who helped make it possible.

• 🎷 Sparkestra: Instrumental World Jazz at PathwaysARTS (Chilmark Tavern), 7-9p / More Info / Free

Saturday, March 21, 2026

• 🐦 Club Birding (Beginner Session) at Featherstone Center for the Arts, 8-10a / More Info

• 🌱 Growing a Healthy Lawn at Wakeman Conservation Center, 2-4p

• 🧠 Weaving Generations: A Multi-Generational Forum on Conflicts in Family Life at Edgartown Public Library, 2-4p / More Info

• 🎨 Guided Somatic Art Meditation: Blooming into Spring with Sally Smith at Stillpoint, 3:30-5p / More Info / $25

• 🎶 Music Street Concert at West Tisbury Public Library, 4p / More Info / Free

• 🍝 10th Annual Meat Ball at Agricultural Hall, 5:30-8:30p / More Info / $50
  Dinner, dancing, and Island-raised meat are all part of this family-friendly Ag Society fundraiser, with vegetarian and alpha-gal-friendly options available.

• 🎤 MVYRADIO’s Sixth Annual Night Out For Nonprofits at Portuguese-American Club, 6-9p / More Info / $20
  A 6p cocktail hour for nonprofit networking is followed by doors opening to the public at 7p and live music from Johnny Hoy and The Bluefish.

Sunday, March 22, 2026

• 🐑 Meet the Lambs – March at Slough Farm, 10a-12p (Sat–Sun) / More Info / Free
  Families can book a 30-minute time slot to meet newborn lambs in a small-group setting, with a maximum of five people per party.

• 🎬 EPiC: Elvis Presley in Concert at MV Film Center, 7:30p (Fri & Sat), 4p (Sun) / More Info
  Archival footage from Elvis’s early 1970s tours and Las Vegas residencies is woven into a hybrid documentary-concert experience highlighting his peak performance era.

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MVacay TLDR

• Sail Martha’s Vineyard is the clearest public-facing place to start if you want the community-access side of Vineyard sailing.

• If you want to experience Vineyard sailing without joining a club, public options like MV Ocean Academy and the Schooner Alabama offer a more approachable way in.

• Vineyard Haven Yacht Club and Edgartown Yacht Club are more exclusive, club-based sailing hubs with junior programs, adult sailing, and regatta ties, but they are not the same thing as broad public access points.

⛵ The Sailing Club Landscape on MV

The sailing scene on MV includes a mix of public programs, private clubs, race groups, and heritage organizations.

Sail Martha’s Vineyard was founded in 1992 to provide free maritime education to young Islanders and to preserve and protect the Island’s maritime heritage. It’s programming includes adult sailing instruction, support for competitive sailors, and other water-based programming. Sail MV also runs SailMobility, an on-the-water program for Islanders of all abilities, which adds an important accessibility layer to the Island’s sailing landscape.

At the same time, Vineyard sailing also includes a more traditional club world. Edgartown Yacht Club, established in 1905, remains one of the Island’s major sailing institutions and a major organizer of regattas. Vineyard Haven Yacht Club also has a strong junior and adult sailing presence. That more formal side is less inclusive, though it is longstanding and influential.

Holmes Hole Sailing Association is a separate local racing group based in Vineyard Haven that welcomes sailors of all skill levels; any monohull boat over 15 feet can join its race series, and VHYC also helps connect people to that scene through crewing and club-boat opportunities.

👧 Where Kids and Teens Can Learn to Sail

If there is one place where the Vineyard sailing ecosystem feels most alive and most reachable, it is youth programming.

Sail Martha’s Vineyard is the most straightforward public-facing option. Its programs include youth sailing instruction, beginner pathways, fall youth sailing, private lessons for all ages, and support for the Martha’s Vineyard Regional High School sailing team. Its broader mission is explicitly community-based, which makes it an important counterweight to the idea that sailing here is only for club kids or families already inside the scene.

Then there is Martha’s Vineyard Ocean Academy, which hosts youth voyages aboard Shenandoah. It has more than 30 years of experience serving ages 7–17, and Shenandoah has hosted hundreds of weeklong youth voyages over the past three decades. Its model is more immersive and voyage-based: living aboard, learning as crew, unplugging, and building confidence through time under sail.

Vineyard Haven Yacht Club and Edgartown Yacht Club both maintain youth sailing infrastructure for youth whose families are members of the clubs.

🧑 Where Adults Can Learn or Get Back Into It

Adult access is where the Vineyard sailing picture gets a little thinner. Sail Martha’s Vineyard is still one of the clearest places to start, with adult instruction and private lessons for all ages. Martha’s Vineyard Ocean Academy’s all-ages voyages can be another way in, especially for people more interested in the experience of sailing than formal instruction.

For adults who want more of a sailing experience than a formal lesson, Black Dog Tall Ships’ Schooner Alabama offers public sails out of Vineyard Haven and gives people a way to get out on the water without entering the club world.

Vineyard Haven Yacht Club and Edgartown Yacht Club also offer private adult lessons to members.

If you are visiting and just want a beautiful, low-pressure way onto the water, private sunset sails like Sail Magic Carpet or Catboat Charters are another easy entry point.

🏆 Regattas, Racing, and the Competitive Side

Sail Martha’s Vineyard’s Vineyard Cup Regatta is one of the clearest nonprofit/public-facing regatta anchors on the Island. It is one of the headline racing events of the season and helps connect community sailing, fundraising, and competition.

Edgartown Yacht Club’s ’Round-the-Island Race is another major centerpiece. The club describes it as one of yacht racing’s oldest distance races, and it remains part of a larger Edgartown Race Weekend. This is one of those events that really reinforces how deeply sailing tradition runs on the Island.

Vineyard Haven Yacht Club also supports a more active race culture than people might assume at first glance, with junior regattas, adult racing, and connections to the regular Holmes Hole racing.

The annual Catboat Parade of Sail in Edgartown also adds a more traditional, heritage-driven layer to the scene, showing that Vineyard sailing culture is not just about competition, but also about classic boats and maritime tradition.

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🏛️ The History and Culture Behind Vineyard Sailing

Martha’s Vineyard Museum preserves and shares the Island’s history, and its collections include materials tied to both island Yacht Clubs.

Ocean Academy and Shenandoah add another layer to that story. Shenandoah has sailed out of Vineyard Haven for decades, and the organization describes it as a long-running educational tradition that has carried thousands of Vineyard children on weeklong voyages. Shenandoah is expected to complete its final season in 2026, making this a transitional moment for that longtime Vineyard tradition.

The sailing landscape also includes the working waterfront: Gannon & Benjamin in Vineyard Haven has helped keep traditional wooden boatbuilding and restoration part of the Island’s sailing identity for decades.