Visiting Martha's Vineyard in Fall 2020

10 Jul 2020
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Martha's Vineyard Seasons

Marthas Vineyard in the fall

While Martha’s Vineyard is popular for its summertime activities, there’s still plenty to do on the island once Fall rolls around. And this year, with more and more schools and businesses going remote, we think fall will become an extension of our summer season, as more people will have the flexibility to travel. 

September is actually one of our favorite months of the year on Martha's Vineyard, and October can be a very enjoyable time to visit as well! The crowds disperse, things quiet down, and it’s easier to get ferry tickets so you can book a luxury vacation home for a long-weekend getaway. Here are a few of our recommendations for things to do on the Vineyard this fall.

Martha’s Vineyard Food & Wine Festival

Experience the island’s rich culinary history at this flagship food and wine event on Martha’s Vineyard. Meet local chefs, farmers, fishermen, and artisans as you enjoy four days and three nights of gourmet meals paired with the perfect wine selections. Tickle your taste buds and don’t forget to make a list of all of the great local restaurants you want to visit. Getting a reservation at some of the Vineyard’s top restaurants becomes much easier when the summer crowds head home.

October 21 - 25, 2020

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Martha’s Vineyard Striped Bass & Bluefish Derby

For nearly 75 years, “The Derby” has been a favorite community event for locals and visitors alike. As stated by one of the derby’s previous presidents, it’s a tournament run for and by fishermen. Originally created to encourage tourism to the Vineyard in the Fall, in recent years the derby has attracted nearly 2,000 fishermen from around the world. Anglers compete for prizes to catch the largest fish including striped bass, bluefish, bonito, false albacore, and weakfish, with divisions for both boat fishing and shore fishing. Proceeds from the derby are used to award scholarships to local high school students.

September 13 - October 17, 2020

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West Tisbury Farmers Market

The West Tisbury Saturday Farmers Market has been a staple for summer visitors to the Island since 1974. Luckily the market will still run this summer, but it cannot be a social experience as it has been in the past. The Farmer's Market is asking patrons to please shop alone if possible, or in very small groups, as only 250 customers are allowed into the market at one time. The larger the groups, the longer the line to get in will be. Visit this page for Farmer's Market 2020 rules:

The market runs through October 10, so fall visitors can enjoy this favorite local attraction as well. Stop by the farmer’s market to browse local agricultural products and delicacies. Pick up some of your favorite seasonal fruits and veggies and make yourself a farm-fresh meal, or buy some local souvenirs to take back to your friends on the mainland.  With over 39 vendors, the West Tisbury Farmer’s Market has grown into a community favorite. This year, the market has been moved to the Fairgrounds at the New Agricultural Hall in West Tisbury.

Summer/Fall Market: Saturdays through October 10, 2020 - 9am - 12pm | Fall Market Saturdays October 19 - December 14, 2019 - 10 am - 1 pm

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Martha’s Vineyard Antique Show

Whether you’re looking for a special antique for your Martha's Vineyard home, something to take back to the mainland, or you just enjoy browsing collectibles for fun, there’s plenty to take in at the Antique Show at Grange Hall in West Tisbury. Held weekly on Fridays through early October and hosted by the MV Antique Association, the Antique Show is the perfect place to scour for everything from eclectic pieces from farm homesteads to treasures from abroad.

Go to the Beach

While the summer season may have officially ended, it’s still warm enough to swim at the beaches of Martha’s Vineyard well into October. And with fewer people visiting the Vineyard in the fall, you won’t have a problem finding a prime spot on some of the area’s most prominent beaches in Aquinnah, Chilmark, Edgartown, or West Tisbury. Take advantage of the smaller crowds you’ll find in the Fall, put together a picnic lunch, and soak in the waning summer sun. Whether you want to explore the water by kayak, sailboat, or wind surf board, or relax under an umbrella in your favorite beach chair, there’s plenty of beach fun to go around.

Art of Chocolate Festival

Most likely Cancelled for 2020 - Calling all chocolate lovers, the Art of Chocolate Festival hosted at the Featherstone Center for the Arts in Oaks Bluff is a sweet treat for all. From traditional chocolate candies to cakes, cookies, and brownies, you’ll leave this festival with your chocolate fix satisfied. In addition to sampling delicious desserts, the festival also includes photos, films, and art featuring your favorite subject: chocolate.

2020 Dates TBD

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Cycle Martha’s Vineyard

Mild Fall temperatures make biking on the Vineyard pleasant and enjoyable. With miles of paved bike trails, and rural island roads, exploring Martha’s Vineyard by bike is a great way to get acquainted with the island while getting some exercise. Cruise through town or drink in the island’s beautiful New England landscape. Didn’t bring your bike with you? Check out some of our favorite bike rental outfitters on the island, and don’t forget to ask them for their local recommendations when you stop by.

From food to festivals to beach fun, come join us in Martha’s Vineyard for our favorite season of the year. Check availability now to find the perfect home for your Fall Martha’s Vineyard getaway.