I’ve become a big believer in seasonal bucket lists! They’re one of the easiest ways to appreciate the charm of MV and the blessing of four distinct seasons. My fall list keeps me accountable to exploring somewhere new and making time for longstanding traditions. Here are my 2026 picks:
🌅 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
More events, new businesses, closures and fall ideas will be added to my Weekend Updates over the next few months, so check back each week for more.
What are you most excited to do this fall? What’s your favorite MV fall tradition?
Tell me in the comments! 🍂