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. The 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. Tuesday, September 6 through Sunday, September 11: Martha’s Vineyard International Film Festival  For 17 years, MV Film Society Executive Director Richard Paradise has been delighting Islanders and visitors alike with films from around the world with the Martha's Vineyard International Film Festival (MVIFF). The MVIFF offers 6 days of movies that will inspire, evoke a range of emotions, take you to other countries and more.

2. Wednesdays & Saturdays through September 10, 9am-2pm: Chilmark Flea Market
Shop high quality handmade items from Vineyard artists and craftsmen, antiques, imports, and vintage finds at the ‘Flea’ in Chilmark! Located at the oldest outdoor venue on the Island, this market is like no other. No admission fee required, and there’s free parking on location at 142 North Road in Chilmark. 

3. Saturday, September 10, 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 11.

4. Saturday, September 17, 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. Rain date September 18.

Photo: Max Bossman, Tivoli Day

5. Sunday, September 11 through Saturday, October 15: Martha’s Vineyard Striped Bass and Bluefish Derby
Now in its 77th 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 boat, and many of them don’t sleep until they catch a winning fish.

6. Saturday, September 17: Potters Bowl
Featherstone's annual Potters Bowl celebrates local potters who work throughout the year to create beautiful bowls which they donate to Featherstone for this special fundraiser. Patrons are able to select handcrafted bowls and are then served a casual summer meal of locally made soup from Island restaurants and caterers (along with Island made bread and desserts!). It's an affordable, community focused event which also raises needed funds for our beloved year round art center.
 
7. Through September: Marine Discovery Tours 
Cruise from Oak Bluffs Harbor with a Felix Neck naturalist to explore the waters of Vineyard Sound aboard The Skipper. Participants will have a chance to look at the catch up-close and to try their hand at scup fishing if time permits. This cruise is a great way to experience the tranquility of the ocean while discovering underwater wildlife. Recommended for ages 4 and up.

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

8. Wednesday, September 28: The 2022 Vineyard Charity Golf Classic
The Vineyard Charity Golf Classic is a tournament that benefits MV Community Services and the Island’s Rotary Club – supporting nonprofits across the Martha's Vineyard community including MV Hospital, Island Health Care, MV Boys and Girls Club, Big Brothers and Big Sisters, Sail MV, The Yard, Island Food Pantry, Councils on aging and more.

9. Wednesdays Through September 28, Saturdays Through October 30: 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 Wednesdays and Saturdays from 9-12pm at the Ag Hall in West Tisbury. The market also returns in the winter and meets indoors on Saturdays from October to December. Be sure to check the most current hours here.

10. Bass in the Grass, September 20 - October 16: Bass in the Grass
The annual Bass In the Grass is part art exhibit, part fundraiser, honoring the Martha's Vineyard Striped Bass & Bluefish Derby, the Island’s annual fall fishing event. Bass in the Grass is a public art exhibit created to raise money for local artists and the Derby Scholarship Fund, which awards scholarships to qualified Vineyard students annually by the Martha's Vineyard Striped Bass & Bluefish Derby, Inc. Starting the fourth week of September, you can view this school of fish in the mini park on Main Street and at the Carnegie in Edgartown and bid on your favorite fish for the chance to have a piece of the Island in your home. 

11. Saturday, October 8: Ladyfest
Ladyfest is an annual female-fueled arts and music festival held in downtown Oak Bluffs that raises awareness and funds for CONNECT to End Violence, a program of Martha’s Vineyard Community Services. The event  features musical artists from many genres as well as food and retail vendors, with proceeds benefitting CONNECT, the local non- profit which aims to reduce domestic and sexual violence and assist victims in need. ​

12. Saturday & Sunday,  October 8 & 9: 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.

13. Friday-Sunday, October 14-16: Women In Film Festival
The Martha’s Vineyard Film Society presents their third annual Women In Film Festival (WIFF). WIFF is a celebration of women as filmmakers: in front of and behind the camera. This festival will feature stories that have not been told from a woman’s perspective.

14. Saturday, October 15: 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. 

Morning Glory Farm Pumpkins

​15. Saturday, October 15, 8am: Martha’s Vineyard Brunch Run
Join a race unlike any other. This race offers both 5K and 10K USATF sanctioned courses which are flat and fast, and the 10K course runs along scenic Atlantic Drive right by the ocean. Immediately following the race, this unique and exciting event includes a post-race "Brunch" party with "over the top" brunch nibbles and refreshing beverages. 

16. Saturday, October 22, 10am-3pm: Harvest Festival
Hosted at the Agricultural Hall in West Tisbury, the Harvest Festival is fun for all ages. Visit local farmers at the Farmers Market, catch a competition at the Island Draft Horse Show, enter the Women’s Skillet Toss, do a fall craft, have some locally made lunch, carve a pumpkin, and so much more!

17. 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. This ever-changing variety of locally grown produce, specialty foods, flowers, indie designers, artisans and vintage dealers has something for everyone, plus live music!

Featherstone Holiday Gift Show

18. Sunday, October 30: 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. Mid-November through Mid-December: 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.

20. November 25: 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.