20 Activities to Enjoy This Fall on Martha’s Vineyard

Photo: Monique Belair, Wind Festival

Thousands of visitors flock to Martha’s Vineyard to soak up those leisurely summer beach days by the seashore, but the Island stays very much awake and vibrant throughout the fall too. Locals love the cooler temperatures and smaller crowds, and the slower tempo makes for more relaxing days to enjoy the Island’s most coveted areas and events.

Here are 20 tempting reasons to fall for Fall on Martha’s Vineyard, and 20 reasons you’ll want to plan a trip before another season passes you by!

1. Saturday, September 7, 10:30am–5pm: Martha’s Vineyard Wind Festival Attention kite lovers of all ages! Come see kites of all shapes and sizes soar above the gazebo at Ocean Park in Oak Bluffs. Activities include kite making and model sailboat racing for children, and kite flying and frisbee games for young and old. Rain date September 8.

2. Saturday, September 14, 10am–6pm: Tivoli Day
This end-of-summer celebration has been going on for decades and is the place to score a good deal on a locally made product or Martha’s Vineyard souvenir. The event takes place on Circuit Avenue in Oak Bluffs, which is closed to cars for the day, as vendors line the streets with their wares, musicians perform, and attendees savor their last taste of summer.

Photo: Max Bossman, Tivoli Day

3. Sunday, September 15 through Saturday, October 19: Martha’s Vineyard Striped Bass and Bluefish Derby
Now in its 74th year “The Derby” is a Vineyard fishing tradition that completely consumes local anglers, and those that visit the Island 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.
 
4. Saturday, September 21: 4th Annual Martha’s Vineyard Craft Beer Festival Beer lovers rejoice! Enjoy your pick of 150 beers from 50 breweries under a big tent at Waban Park in Oak Bluffs. Sample your favorites and discover new brews.
 
5. 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 appreciate the painted skies of Martha’s Vineyard. 

Photo: Mark Alan Lovewell, MV Striped Bass and Bluefish Derby

6. Friday, September 27 & Saturday, September 28: Martha’s Vineyard Fashion Week
Returning after a five-year hiatus and hosted by Dressed MV, two shows will be held at the Vineyard Arts Project in Edgartown featuring looks from local designers including Conrado, Roy Bikini, American Rhino,The Green Room, Citrine x Trust, June, The Glasshouse and more. Tickets available in stores and online. 

7. Saturdays through October 12: West Tisbury Farmers Market.
The open air West Tisbury Farmers Market was established in 1974 and has been operating ever since, making it the Island’s oldest market, and the go-to spot for the freshest food around. In the fall the market continues to pop up on Saturdays from 9-12pm at the Grange Hall in West Tisbury. The Market also returns in the winter and meets indoors at the Agricultural Hall in West Tisbury on Saturdays from October to December. Be sure to check the most current hours here.

8. Saturday & Sunday, October 12 & 13: The Art of Chocolate Festival
For eighteen 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 in any form your heart desires.

​9. Sunday, October 13: Vineyard Artisans Columbus Day Festival
Vineyard Artisans resurrects its weekly summer festival especially for Columbus Day, offering 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.

10. Sunday, October 13: Popcorn Festival at Native Earth Teaching Farm
Pop in for free popcorn all day from 10am-3pm and enjoy fall fun at this small working educational farm in Chilmark.

11. Wednesday, October 23 through Sunday, October 27: Martha’s Vineyard Food & Wine Festival
This four day food and wine event brings together top culinary talents from the Island and beyond, along with world class winemakers, local farmers and discerning foodies for the ultimate taste of the Island experience. For the first time special guest and acclaimed chef Daniel Boulud will host an intimate five-course French dinner at Bettini Restaurant at the Harbor View Hotel. 

Morning Glory Farm Pumpkins

​12. October 19: Morning Glory Pumpkin Festival
The largest farm on Martha’s Vineyard hosts this lively free fall festival each year, complete with pumpkin games, hayrides, live music, and all things pumpkin.

13. Sundays through October: Oak Bluffs Open Market
Experience this super combination of Farmers Market, Artisan Fair, Vintage Flea Market and Body, Mind, Spirit Fair–all together at Washington Park in Oak Bluffs. The ever-changing variety of locally grown produce, specialty foods, flowers, indie designers, artisans and vintage dealers offers something for everyone…plus live music!

14. Wednesdays 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 November. Show up with your favorite toppings, mingle with the locals and meet some new friends.
 
15. Saturdays through October: Honey Farm Bee Hive Tours
Experience the life of bees along with a beekeeper from Ginny Bee Honey Farms for a small group tour. Learn about the world of bees and how valuable they are to our food and our environment. You'll assist in finding the queen, measuring honey, identifying pollen, and monitoring bee life cycles. 

Classic Aviators

16. Through mid-October: Take a Classic Aviators Biplane Ride  
Take in the best view of Martha’s Vineyard from high in the sky. Enjoy breathtaking scenery and sights that can only be viewed from above while learning about the history of the Island.
 
17. 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.

18. Sunday, October 27: 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. 

19. Friday, November 15 - Friday, December 13: 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.
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20. November 29: Felix Neck Wildlife Sanctuary Fall Festival
This celebration of fall is a Vineyard tradition. Held the day after Thanksgiving, it 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.