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Martha’s Vineyard Events and Festivals

Martha’s Vineyard may be a small island, but we can throw a party with the best of them. Plan your next visit around one of our annual events and festivals to get the full experience while you’re here.

Big events, like the annual Martha’s Vineyard Food & Wine Festival and Christmas in Edgartown weekend, attract visitors from near and far, while smaller happenings leave plenty of local charm to discover during every trip to the island. From craft fairs packed with local artisan flair to culinary tours and the occasional alpaca yoga class, check the calendar to see the latest Martha’s Vineyard events taking place during your stay.

Our Favorite Seasonal Happenings

Every year, Martha’s Vineyard enjoys a hosts of seasonal festivals, firework shows, foodie frenzies, and holiday celebrations. Here are just a few highlights from our busy annual calendar:


Martha’s Vineyard’s opens the season with The Annual Big Chili Contest. Held during May at the PA Club in Oak Bluffs to benefit local non-profits, entrants and chili fans from far and wide come to compete and judge in this mid-winter party and eat-a-thon. The Mariachi band gets you in the spirit and the fun goes all day.

Martha’s Vineyard Film Festival

The mission of the Martha’s Vineyard Film Festival is to “produce community events, educational programs, and films that spark discussion, debate, and action.” Showing independent films from around the world, it’s an event any movie buff will enjoy.

MV Wine Festival

Kick off the summer with a weekend of good food, good wine, and, of course, plenty of good people. The Martha’s Vineyard Wine Festival started only a few years ago, but has already established itself as an island staple. Events range from craft beer tastings to cocktail competitions to the Grand Tasting.

Independence Day

Old school Americana at its best! Hot dogs and burgers on the Whaling Church lawn, antique cars and fun floats. Vineyard Square is the best spot to see the parade as it goes right past the front of the hotel. Then, stroll up North Water Street to stake out your spot for the fireworks.

Illumination Night

The mid-August Illumination Night tradition at the campgrounds began more than a century ago and the format remains — a community sing-along as dark falls then the lighting of the beautiful Chinese and Japanese lanterns that adorn the cottages. Not to be missed!

Martha’s Vineyard Agricultural Society Fair

The annual Martha’s Vineyard Agricultural Society Fair starts on the third Thursday of August and runs through the weekend. Look forward to everything from animal shows to crafts and competitions.

The Oak Bluffs Fireworks

On the third Friday of August, prepare for the biggest celebration of summer on Martha’s Vineyard. Gather in Ocean Park, where music in the Gazebo starts around 8:00 pm. Spectacular fireworks begin at dark. Take public transportation (buses run continuously between Oak Bluffs and Edgartown before and after the show), it is much easier than circling for hours looking for a parking spot!

Food & Wine Festival

October brings this annual culinary treat — workshops, tastings, wine dinners and the Grand Tasting make this a “must do” for foodies. Our location puts you at “Getaway Central” to walk to most of the main events!

Christmas in Edgartown

The second weekend in December brings caroling, horse drawn carriage rides, a parade and lots of holiday cheer to Edgartown. Breakfast with Santa on Sunday morning thrills the kiddies — Santa leaves the sleigh behind and arrives by Fire Engine. Discover more about this classic Edgartown event in this post from our blog!

Photo:  Massachusetts Office of Tourism & Travel / Flickr CC BY-ND 2.0.

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