🍁 MVacay’s Fall Guide to Martha's Vineyard (2025)

Month-by-month picks for seasonal favorites and Martha's Vineyard traditions

Sep 08, 2025

Welcome to your Fall Guide to Martha’s Vineyard! I always come back to a familiar set of fall bucket list items, with a few new additions each year depending on what locals are innovating on.

This guide isn’t a full events calendar (you’ll still find those in my weekly Weekend Updates). Instead, it’s a month-by-month look at seasonal favorites you can do anytime, plus a few anchor traditions and community gatherings.

🌅 September

The Derby signals fall in full swing. Restaurants keep summer hours through mid-month, then gradually shorten as the month winds down.

Things to Do Anytime

Try a farm or food class — Mermaid Farm’s feta-making, Slough Farm’s cooking nights, or FARM Institute workshops.
Shop early-season sales at shops in Oak Bluffs and Edgartown — September is when summer stock gets cleared out.
Make a back-to-school tote at Tote@lly Yours — a fun, creative project to carry through the off-season.
Catch a film at the MV Film Center or a live performance at MV Playhouse.
Drive to Menemsha for a sunset and enjoy the easy parking
Evening Reset: trivia at The Wharf, a library author talk, or a quiet dinner at a restaurant that was impossible to get into in July (Alchemy, Détente, Sweet Life).

Dates to Know

Sept 14–Oct 18 — MV Striped Bass & Bluefish Derby: A fall tradition; weigh-ins on Dock Street in Edgartown are free to watch and mark the island’s seasonal rhythm. Kids Derby Day 9/21.
Sept 18–23 — Martha’s Vineyard Songwriting Festival: Songwriters and performers mix workshops with concerts, giving the island a mini music week.
Sept 20 — Tivoli Day (Oak Bluffs): Circuit Ave shuts down for a block party with music, food, and sales — the island’s unofficial “locals’ summer” celebration.

🎃 October

Columbus Day / Indigenous Peoples’ Day is a big turning point for the season. Many shops and restaurants close after that weekend. Leaves and temperatures begin to change. Seasonal homeowners and tourists stop coming, and ferries to Oak Bluffs stop running.

Things to Do Anytime

Take garden strolls when foliage starts to turn: Mytoi Gardens on Chappy or Polly Hill Arboretum are peaceful paths you can venture to see the most stunning leaves.
DIY Farmstand Crawl - it’s pumpkin season at Morning Glory Farm: pick your own, grab goodies from Beetlebung or Mermaid Farm.
Make a custom charm necklace at Stefanie Wolf Designs.
Try a new-for-2025 restaurant - Ocean Club, Indigo or The Maker.
Do a thrift + vintage loop to refresh your fall wardrobe or donate old clothes.
Walk usually permit-only beaches that re-opened for fall sunsets including Lambert’s Cove or Lucy Vincent.

Dates to Know

Oct 5 — Gay Head 10K: A signature up-island race finishing at the lighthouse, one of the most scenic runs of the year.
Oct 11–12 — Vineyard Artisans Holiday Show: The first holiday shopping push, packed with local makers.
Oct 18 — Morning Glory Pumpkin Festival: Hayrides, baked goods, and family fun — an island fall tradition.
Oct 25 — Harvest Festival (Ag Hall): A day of animals, food, and music that feels like the community’s fall gathering. Ponies and Pumpkins (Misty Meadows) is another great option too!
Oct 25–31 — Halloween Celebrations: Oak Bluffs parade, Vineyard Haven’s puppet parade, and Edgartown’s Happy Haunting — each town adds its own flavor, from family-friendly to all-out costumes.

🦃 November

Weekdays grow quiet, but weekends center on markets, music, and films. An uptick of re-openings and holiday traditions occur the last week of the month.

Things to Do Anytime

Shop early at holiday markets: Featherstone’s Holiday Gift Show opens mid-month, with Vineyard Artisans and gallery pop-ups following.
Sign up for an adult learning workshop at a library.
Family-friendly indoors: open skate at MV Ice Arena, bowling at The Barn, or kids’ crafts at the MV Family Center.
Volunteer: MV Community Services and the Island Food Pantry both welcome seasonal help but plan ahead.

Dates to Know

Nov 8 — Barn Raisers Ball (Ag Hall): More than a dance — this is the community reunion, where generations gather to celebrate the season.
Nov 28 — Felix Neck Fall Festival: A Thanksgiving-weekend tradition for families across generations; hayrides, cider, and nature crafts make it a Vineyard classic.
Nov 29–30 — Vineyard Artisans Thanksgiving Festival: Holiday shopping at its peak — not just a market, but the marker of the season’s start.
Nov 29 — Light Up Oak Bluffs: Circuit Ave glows with lights and carols — the moment the holiday season feels official on MV.

✨ Winter Preview + Practical Tips

Fall is the Vineyard’s sweet spot: a little quieter, but full of community energy. Once Thanksgiving passes, winter begins — quieter weekdays, cozy nights in, and annual holiday anchors like Christmas in Edgartown.

What closes when:

Mid-October is the pivot: many seasonal shops and restaurants close after Columbus Day.
About 20% stay open through New Year’s Eve, and 10% are year-round.
November brings shorter hours midweek, but weekends are stacked with markets and music.

THIS is where I’ll keep closure updates and restaurant dates, refreshed weekly through fall and winter: