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Events on Martha's Vineyard - Summer 2014

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.

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Cape Cod


A Taste of the Vineyard Gourmet Stroll
June 12
The Taste of the Vineyard is the kick-off to the Vineyard's summer social season. Thursday night's Gourmet Stroll offers the Island's best food, wine and hand-crafted beers from over 75 outstanding fine food and beverage participants. Then, dance to Jerry Bennett and the Sultans of Swing's 12 piece band.(

Annual OB Harbor Festival
Oak Bluffs
June 21
Each year's Harbor Festival surpasses the record crowds of the previous year. Over 40 vendors from near and far, including many of the Vineyard favorites plan to return for one of the Island’s most popular events. Local artists, craftsmen and antique dealers, as well as non-profit organizations offering a tempting array of baked goods, raffles and information about their causes, will be on hand. Live music on the deck at Nancy’s featuring Martha's Vineyard's favorite bands. As always, an abundance of native seafood and gourmet treats await the festive gathering at this year’s Harbor Festival.

Martha's Vineyard Restaurant Week
June 15 - June 19
Join us for the annual Martha’s Vineyard Restaurant Week. Enjoy 3-course dinner menus priced between $25 -$45 and lunch menus priced between $10 and $20 at some of the Vineyard's most popular restaurants

Oak Bluffs Summer Solstice Celebration
Oak Bluffs
June 19
Oak Bluffs welcomes the arrival of summer at its annual solstice celebration, 6-8pm on Circuit Avenue. Music, arts, crafts and lots of family fun in the lingering twilight of the year's longest day.

Edgartown Independence Day Parade
July 4
The Town of Edgartown's 4th of July parade is a long-standing tradition filled with fun for the entire family. As the parade winds through downtown and around each corner, you will see kilt-clad bagpipers, veterans, floats promoting the island's many non-profit organizations, firetrucks, animals, and a whole lot of candy and excitement. A can't miss annual event.

4th of July Fireworks Celebration
July 4
Cap off a fun-filled star-spangled banner day by watching a spectacular fireworks celebration with family and friends along Edgartown Harbor. This years' celebration will be one of the best. So put on your red, white and blue and wish America a happy birthday

Vineyard Cup
Vineyard Haven
July 11 - July 13
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!

Martha's Vineyard Garden Tour
West Tisbury
July 23
Down dirt roads and hidden behind stone walls are some spectacular Vineyard gardens; join us for this special tour to visit a few. This year we visit gardens in Indian Hill, Tashmoo, and West Chop. Lunch, transportation, and afternoon refreshments provided. Please pre-register by calling 508-693-9426, space is limited and tour usually sells out quickly.

Round-the-Island Race
July 26
The Edgartown Yacht Club's Race Around Martha's Vineyard Island is held on Saturday, July 26, 2014. 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 27
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.

Martha's Vineyard African American Film Festival
August 5-August 9
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 7-August 10 and August 16-August 19
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 20
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.

Fireworks at Ocean Park by the Sea
Oak Bluffs
August 22
This is a fun night to spend out with family and friends. Oak Bluffs is a great place to do it. Grab dinner at one of the many fine restaurants in the area, then maybe an ice cream... and then head over to the park for the show. Music by the Vineyard Haven Band in the gazebo begins at 8 pm, fireworks at dark! It is truly one of the best events of the summer.

Martha's Vineyard Wind Festival
Oak Bluffs
September 6
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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About Elizabeth Weedon

About Elizabeth Weedon: I have worked for since 2008, and I've been a loyal homeowner listed on the site since early 1998. An enthusiastic member of the Homeowner Support Team, I provide fellow Cape and Islands vacation rental homeowners with advice about online marketing and rental management techniques to ensure them a successful rental experience each season. In addition to phone and email support to our homeowners, I also create and edit much of the content on our website, as well as our Homeowner Blog and monthly newsletters. I am also the Press & PR Coordinator for the company, responsible for drafting our press releases and responding to press inquiries and interviews. I grew up summering on the Vineyard, where I have managed my family's rental home since the mid-1980's, and I'm passionately devoted to the Island. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie.