Activities to Enjoy this Fall on Martha’s Vineyard

Martha’s Vineyard may be synonymous with leisurely summer beach days by the seashore, but the Island stays very much awake and vibrant throughout the fall months. The locals love the cooler temperatures and lessened crowds, and the slower tempo makes for more relaxing days to enjoy the nearby sights and sounds. Here are some more reasons to fall for fall on Martha’s Vineyard, and 20 reasons you’ll want to plan a trip before the season passes you by. ​

Martha's Vineyard Food & Wine Festival

September 15–October 6: The Martha’s Vineyard Playhouse presents The Room Where I Was Held Written by David Zax and directed by MJ Bruder Munafo, this play marks the last performance of the season on the Patricia Neal Stage. It’s the world premiere of a gripping drama about the power of money, privilege, and family ties and a great excuse to visit the MV Playhouse, our local hub for theater buffs and those that love a good show.

September 22: Martha’s Vineyard Craft Beer Festival Craft Beer Festival Beer lovers rejoice! Enjoy your pick from 150 beers from 50 breweries under a big tent at Waban Park in Oak Bluffs. Sample your favorites and discover new brews.

Through September Sunset & Moonrise Kayak Tours: Join Felix Neck Wildlife Sanctuary for a paddle on Sengekontacket Pond and take in a breathtaking sunset or spectacular moonrise. Sit back, relax and appreciated the painted skies of Martha’s Vineyard.

October 6 & 7: The Art of Chocolate Festival For fifteen years Featherstone Center for the Arts, the Island’s year round art haven in Oak Bluffs, has celebrated all things chocolate. This tasty festival features two days of all-out chocolate consumption. Enjoy the heavenly experience of sampling every morsel of chocolate your heart desires.

October 7: Vineyard Artisans Columbus Day Festival The Vineyards Artisans resurrect their weekly summer festival especially for Columbus Day and it’s the ultimate destination for shopping local on Martha’s Vineyard. Meet the artists themselves and browse their impressive products including textiles, fine furniture, pottery, leather goods, oil paintings, pastels, mixed media, sculpture, wampum jewelry, hand-knit items, clothing, photography, handmade books, and more.

​October 7: Popcorn Festival at Native Earth Teaching Farm Pop in for free popcorn all day from 10-3pm and enjoy fall fun for the whole family.

Martha's Vineyard Striped Bass & Bluefish Derby

Through October 13: Martha’s Vineyard Striped Bass and Bluefish Derby Now in its 73rd year “The Derby” is a Vineyard fishing tradition that completely consumes local anglers, and those that visit especially for it. Participants vie for big prizes including a car and a boat, and many of them don’t sleep until they catch a winning fish.

October 17–21: Martha’s Vineyard Food & Wine Festival This 4-day food and wine event brings together the Island’s top culinary talents and beyond, along with world class winemakers, local farmers and discerning foodies for the ultimate taste of the Island experience.

October 20: Morning Glory Pumpkin Festival The largest farm on Martha’s Vineyard hosts this lively free fall festival each year, complete with pumpkin games, hay rides, live music, and all things pumpkin.

Through October: Pizza Nights at Orange Peel Bakery This charming up-Island bakery welcomes the community to stop by and enjoy pizza together every Wednesday night from 5-8pm through September and October. Show up with your favorite toppings, mingle with the locals and meet some new friends.

Through October: Take a biplane ride with Classic Aviators Take in the best view of Martha’s Vineyard from high atop the sky. Enjoy breathtaking scenery and sights that can only be viewed from above while learning about the history of the Island.

Through October: Island Alpaca Yoga Calling all yoga loving animal enthusiasts! Island Alpaca farm hosts a 1-hour session of relaxing yoga, held in a pasture among their friendly alpaca. Please pre-register.

The month of October Fall for the Arts Each fall, Martha’s Vineyard, along with Cape Cod and Nantucket, dedicates the entire month of October to a celebration of the arts. Fall for the Arts strives to initiate and sustain conversations among artists, patrons, and the public.

October 28: Happy Haunting This event encompasses Edgartown’s annual Halloween festivities, and things can get spooky. Visit downtown Edgartown for some Halloween fun, while little ghosts and goblins trick-or-treat from business to business. Sponsored by the Edgartown Board of Trade.

November, 17–December 16: Featherstone Holiday Gift Show Featherstone Center for the Arts is the place to go for unique, one of a kind holiday presents made right here on Martha’s Vineyard. It’s gifts galore for a whole month, including apparel and accessories, cards, calendars, jewelry, pottery, photography, paintings, ornaments, and more. All sales benefit local Vineyard artists and Featherstone, the Island’s only not-for-profit year-round art center.

November 23: Felix Neck Wildlife Sanctuary Fall Festival This celebration of fall is a Vineyard tradition held the day after Thanksgiving and features hayrides, face painting, live music, food, wreath making, a weather station and crafts for kids, live animals, trail walk, and fun to be had by the whole family.

Ongoing: Enjoy the Island’s tastiest restaurants. Many of the Island’s seasonal restaurants stay open well into the fall, not to mention the dozens of others that stay open all year. Come sample some of the Island’s best dishes without having to wait in line or needing a reservation.

Pumpkin Festival at Morning Glory Farm

For a full list of everything happening this fall, visit the EVENTS tab on our website.