Best of the Vineyard 2016 Events and Entertainment

The votes are in, the ballots have been counted. And the winners are...

Best Live Music Venue: The Ritz

4 Circuit Avenue, Oak Bluffs, 508-693-9851,

Runner-up: The Port Hunter

55 Main Street, Edgartown, 508-627-7747,

The Ritz has quickly become the go-to venue whenever you’re in need of a live music fix. This legendary dive bar hosts Island-favorite bands most every night, all year long. Locals couldn’t be more pleased. The Port Hunter comes alive in the summer and provides choice bands from both on-Island and off.

Ain’t no party like a Taste of the Vineyard Party, ’cause a Taste of the Vineyard Party matches plastic cups with pastel suits.
Elizabeth Cecil

Best Charity Event: A Taste of the Vineyard, Martha’s Vineyard Preservation Trust

Dr. Daniel Fisher House lawn, Main Street, Edgartown, 508-627-4440

Runner-up: Possible Dreams Auction, Martha’s Vineyard Community Services

Winnetu Oceanside Resort, 31 Dunes Road, Edgartown, 508-693-7900

Nibble, sip, dance, repeat. Nantucket Reds definitely required. Partygoers kick off the bustling summer season at the Preservation Trust’s A Taste of the Vineyard, a perennially sold-out event. Later in the summer the Possible Dreams Auction makes dreams a reality. Want to hang out with Seth Meyers? Bid enough and you can.

Best Movie Theater, Festival, or Series: Martha’s Vineyard Film Center

Tisbury Marketplace, 79 Beach Road, Vineyard Haven, 508-696-9369,

Runner-up: Entertainment Cinemas

65 Main Street, Edgartown, 508-627-8008,

Comfy stadium seats: check. A constantly full calendar of film festivals, new movies, documentaries, and classics: check, check, check, and check. At the state-of-the-art Film Center, there is a movie for any taste. If blockbuster hits are more your style, Edgartown Cinemas’ two screens have you covered. The newest releases are always playing.

Best Live Band or Musician: Johnny Hoy and the Bluefish


Runner-up: The Joanne Cassidy Band


The bluesy tunes of Johnny Hoy and the Bluefish are sure to get anyone on the dance floor. It’s not hard to catch this rockin’ band during the summer – you can find them at everything from fancy fundraisers to dive bars. If you’re in the market for a high-energy band to get you grooving, the Joanne Cassidy Band is a must.

Libby Iandoli wins for cutest smile.Her trusty flying steed wins for Best Family Activity.
Elizabeth Cecil

Best Family Activity: Flying Horses Carousel

33 Lake Avenue, Oak Bluffs, 508-693-9481

Runner-up: The Barn, Bowl & Bistro

13 Uncas Avenue, Oak Bluffs, 508-696-9800,

The calliope music draws you in. The allure of catching the brass ring keeps you riding again and again. Now in its 141st season, the Flying Horses Carousel continues to delight families with its antique horses and timeless fun. At the new Barn, Bowl & Bistro, hoots and hollers are regularly heard when someone, probably Jared, bowls a strike.

Best Off-Season Event: Christmas in Edgartown

Various locations,

Runner-up: Martha’s Vineyard Striped Bass & Bluefish Derby

Weigh Station, Dock Street, Edgartown,

Edgartown transforms into a winter wonderland each December during the Christmas in Edgartown weekend festival. From a parade, crafts, and sleigh rides to the lighting of the Edgartown Lighthouse, there is fun for all ages. Fall on Martha’s Vineyard is for the fishermen, who crowd the beaches to vie for the top spot on the Derby leaderboard.

Best Performing Arts Organization: Martha’s Vineyard Playhouse

24 Church Street, Vineyard Haven, 508-696-6300,

Runner-up: The Yard

1 The Yard, Chilmark, 508-645-9662,

All year long the Martha’s Vineyard Playhouse pumps out superb entertainment. From poetry cafés and movie nights during the winter to outdoor theater and full productions in the summer, they know how to keep folks entertained. The Yard, tucked away on Middle Road in Chilmark, brings in numerous dance companies during the summer season to showcase what they do best.

Best Summer Event: Martha’s Vineyard Agricultural Society Livestock Show and Fair

35 Panhandle Road, West Tisbury, 508-693-9549,

Runner-up: Oak Bluffs Fireworks

Ocean Park, Oak Bluffs, 508-693-0077

End your summer with a bang – literally. Each August the four-day Agricultural Fair kicks off on a Thursday. Devotees wouldn’t dare miss the Ferris wheel, fried food, or livestock barn. On Friday of that same week, the sky above Ocean Park comes alive with fantastic colors during the always-popular fireworks show. A perfect grand finale for the summer.