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Martha’s Vineyard Events 2021

Jennie Sparrow | 6/23/2019 (updated 6/17/2023)
Vineyard Haven / Oak Bluffs Band Concerts
photo by Becky Luce

Enjoy Martha’s Vineyard’s wide variety of special events, many of which are free and require no advance planning. In addition to the beautiful beaches, outstanding cuisine and quaint little villages on the Island, events geared to all ages abound – from festivals to Island history and nature tours.

Vineyard Cup
Vineyard Haven
July 10 - July 11
Sponsored by Sail Martha’s Vineyard, this is a weekend of sailboat racing with post race parties that are open to the public. Plenty of food, drink, and music!

Round-the-Island Race
July 22 - 24
The Edgartown Yacht Club’s Race Around Martha’s Vineyard Island is held on Saturday, July 22, 2021. The course around the Vineyard passes in sight of the seven lighthouses of Cape Poge, Gay Head, Tarpaulin Cove, Nobska, West Chop, East Chop and Edgartown. In the morning, the fleet sails between Martha’s Vineyard and Nantucket along the east beach of Chappaquiddick. By mid day, they are in the open Atlantic Ocean with views of the south coast of the Vineyard. In the afternoon, rounding the gorgeous cliffs of Gay Head, the fleet sail up Vineyard Sound.

Possible Dreams Auction
July 25
The Possible Dreams Auction is held as a benefit for Martha’s Vineyard Community Services. The idea for an ‘unbuyable opportunities’ auction was brought to Community Services by Sandy Ray, then chair of the Fundraising Committee. The Possible Dreams Auction is one of the oldest, most enduring celebrity concept auctions and over the years, the Auction Committee has raised over $8 million dollars in support of unfunded care provided by the five programs of Martha’s Vineyard Community Services. In past events, successful bidders have walked across the Brooklyn Bridge with David McCullough; and toured the set of Ghostbusters with Dan Aykryod. They visited and performed on the sets of numerous TV shows, traveled to amazing locales, lunched and supped with some of the country’s most interesting characters, enjoyed concerts, theater performances, behind-the-scene museum tours and award shows unavailable to the public. This year's event will be virtual.

Martha’s Vineyard African American Film Festival
August 6 - 14
Martha’s Vineyard African American Film Festival will showcase films - shorts, features & documentaries - judged to be the "best of the best" in independent African-American cinema.

Built on Stilts Dance Festival
Oak Bluffs
August 12 - 11, and August 21-24
Built on Stilts is a creative playground for both children and adults, from beginners to professionals, representing diverse stylistic backgrounds. Over the years, the event has showcased ballet, modern, hip hop, jazz, tap, breakdance, bellydance, tai chi, movement theater, circus arts, pilates-based dance, mime, improvisation, spoken word and, of course, a bit of stilting. Each performance opens with an improvisational drum circle open to all willing musicians. The rhythms bouncing down Circuit Avenue draw in passersby, who flood the gates of the historic Union Chapel in Oak Bluffs, which has housed the festival since its inception.

Grand Illumination Night
Oak Bluffs
August 21
Gather at the MV Camp Meeting Association’s Tabernacle for a sing-along followed by the annual Grand Illumination when the hundreds of lanterns hung on gingerbread cottage porches are lit. This tradition, dating from the turn of the 19th century, will delight the whole family. Sing along starts around 7 pm and the lanterns are lit at dark.

Vineyard Artisans Labor Day Festival
West Tisbury
September 3-5
This event is the largest art show on Martha’s Vineyard! It features unique furniture, clothing, ceramics, jewelry and fine art from the Islands top artists, and there’s even live music. Watch a weavers weave, a young Island artist create his latest masterpiece, and listen to the Island’s only female blacksmith explain how she forged her lovely brackets!

Martha’s Vineyard Wind Festival
Oak Bluffs
September 11
A Celebration of the Wind - One of Martha’s Vineyard’s most precious resources. What better way to say goodbye to summer, than to hold one BIG Event for everyone to enjoy. We want to do it the old fashioned way, with fun and a creative twist. We encourage creativity and colorful imagination. Everyone is welcome to participate. Remember the simple pleasures that are powered by the wind? There will be Kite Flying, Sailing, Wind Surfing, frisbees, and flying contraptions galore. Exhibits, Artisits and Non-Profits. Competitions and prizes. And don’t forget to bring your blanket and a picnic.

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