Best Charity Event: 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
Grab your complimentary wine glasses, balance those plates (and heels), and sample the best food the Vineyard has to offer, all in one place, at this kickoff-to-summer event. The Taste benefits the Martha’s Vineyard Preservation Trust, which restores and preserves Island architectural treasures. In July, take up the paddle at the annual Possible Dreams Auction, where dreams like stargazing with Inspector Gadget come true.
Best Live Band or Musician: Johnny Hoy and the Bluefish
508-696-3007, johnnyhoyandthebluefish.com
Runner-up: The Mike Benjamin Band
508-642-0439, mikebenjaminmusic.com
Dust off those boots, leave the long day at the door. Johnny Hoy and the Bluefish are here to help lift your spirits by dancing your cares away. Catch them on Memorial Wharf or at The Ritz, and always at the Barn Raisers’ Ball. The Mike Benjamin Band covers a mean tune and knows how to get the bar or wedding party fired up.
Best Live Music Venue: The Ritz
4 Circuit Avenue, Oak Bluffs, 508-693-9851, theritzmv.com
Runner-up: Flatbread Company
17 Airport Road, Edgartown, 508-693-1137, flatbreadcompany.com
Locals know that the Ritz is the place to go for fun, authentic music and dancing any time of year. And it only gets livelier in the summer. The walls of Flatbread have been alive with music since the heydays of the Hot Tin Roof. World-famous and Island-famous acts regularly share the stage.
Best Movie Theater, Festival, or Series: Martha’s Vineyard Film Center
Tisbury Marketplace, 79 Beach Road, Vineyard Haven, 508-696-9369, mvfilmsociety.com
Runner-up: Entertainment Cinemas
65 Main Street, Edgartown, 508-627-8008, entertainmentcinemas.com/locations/edgartown
With its independent film selections, comfy seating, and fancy snacks, the Film Center brings big-city entertainment to our little Island. State-of-the-art digital technology, surround sound, and 3D capability make Entertainment Cinemas in Edgartown the place to go for big blockbusters.
Best Off-Season Event: Christmas in Edgartown
Various locations, edgartownboardoftrade.com
Runner-up: Martha’s Vineyard Striped Bass & Bluefish Derby
Weigh Station, Dock Street, Edgartown, mvderby.com
Picturesque Edgartown gets holly jolly each year with a festive parade down Main Street. There’s fun for all ages, but kids are the real winners, with activities, holiday crafts, and treats throughout the weekend. Santa even comes to town, so bring your list. Derby days in the fall lure anglers of all ages to make their marks on the leader board.
Best Performing Arts Organization: Martha’s Vineyard Playhouse
24 Church Street, Vineyard Haven, 508-693-6450, vineyardplayhouse.org
Runner-up: The Yard
Off Middle Road, Chilmark, 508-645-9662, dancetheyard.org
The Martha’s Vineyard Playhouse has top-notch theater productions, a winter cabaret, musical performances, Monday night specials, outdoor shows at the Tisbury Amphitheater, and a Summer Stars Theater Arts Camp – to name just some of the offerings. Plus, after extensive renovations that wrapped up last year, it’s looking better than ever. During the summer, the Yard hosts artists in residence and a children’s dance camp at its Chilmark campus, as well as weekly performances through September.
Best Summer Event: Martha’s Vineyard Agricultural Society Livestock Show and Fair
35 Panhandle Road off State Road, West Tisbury, 508-693-9549, mvas.vineyard.net
Runner-up: Oak Bluffs Fireworks
Ocean Park, Oak Bluffs, 508-693-0077
It is, by all accounts, the best week of the summer, when August treats the Island to Ferris wheel rides, fried dough, and fireworks. Want to toss a skillet? Win an award for a pie? Watch a lumberjack competition? You can do it all at the fair. If you want to catch the fireworks up close, stake out your spot at Ocean Park early – blankets start dotting the lawn hours before the big show. You might even catch a glimpse of the presidential motorcade passing by.
