Best of the Vineyard 2020: Events and Entertainment

Everything you need to know about events and entertainment on Martha’s Vineyard according to you.

Best Charity Event: Taste of the Vineyard

Dr. Daniel Fisher House lawn, 
99 Main Street, 

Martha’s Vineyard 
Teddy Bear Suite

Nevin Square, 
29 Winter Street, Edgartown,

It feels good to give back. It feels even better when giving back allows you to dress up and sip wine while tasting bites from Island chefs and snapping pictures with your friends at the Taste of the Vineyard gourmet stroll. The Martha’s Vineyard Teddy Bear Suite, part of Christmas in Edgartown, supports the Healthy Happy 
Kids program.

Best Family Activity: Flying Horses

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

Martha’s Vineyard Museum

151 Lagoon Pond Road, 
Vineyard Haven, 508-627-4441,

The nation’s oldest platform carousel has been a good old-fashioned summertime delight for more than a century. While the recorded Wurlitzer band organ plays, riders reach for the brass ring in hopes of scoring a free ride. The Martha’s Vineyard Museum inspires visitors to discover and explore the Island’s rich heritage. 

Best Live Band 
or Musician: 
Johnny Hoy and 
the Bluefish


Runner-up: Vineyard Sound


Nobody gets a crowd on their feet the way Johnny Hoy and the Bluefish do. From weddings to dive bars, playing jazz to Cajun to country to rock, if Johnny and the band are in the house, the house is going to come down. The changing cast of collegiates in Vineyard Sound have been harmonizing around the Island since 1992. 

Best Live Music Venue: The Ritz Cafe

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

Old Whaling Church

89 Main Street, Edgartown, 508-627-4440,

The Ritz remains the Island’s go-to for rollicking, rowdy, boogie-down fun. With a packed schedule of live music, there’s always something to tap your foot to. The Old Whaling Church, a historic space for a more intimate type of show, is part of the MV Concert Series and MV Chamber Music Society.

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

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

Entertainment Cinemas

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

More than a movie theater, the Martha’s Vineyard Film Center is an arts organization that celebrates the best of the movie world, from independent films, documentaries, and classic cinema to educational programs, special events, and even virtual screenings in the age of social distancing. Entertainment Cinemas in Edgartown has a classic movie theater vibe and the latest blockbusters.

Best Off-Season Event: Christmas in Edgartown 

Downtown Edgartown,

Martha’s Vineyard Striped Bass & Bluefish Derby

Dock Street, Edgartown, 

The non-stop energy normally associated with summer returns for one magical winter weekend with Christmas in Edgartown. Holiday cheer abounds during three busy days of merrymaking and one highly anticipated parade. For seventy-five years fishermen and women have cast their eyes and rods on Island waters in hopes of winning big in the Derby.

Best Performing 
Arts Organization: 
Martha’s Vineyard Playhouse

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

Vineyard Sound


The Martha’s Vineyard Playhouse offers live, professional theater year-round in a historic downtown location. While their schedule has been upended this year, their mission to inspire, enrich, and entertain from childhood to adulthood remains unchanged and more important than ever. The Vineyard Sound performs around the Island from early June through August.

Best Radio Station: WMVY – 88.7 FM

121 Carroll’s Way, 
Vineyard Haven, 508-693-5000,

WCAI Cape and Islands NPR – 90.1 FM

3 Water Street, Woods Hole, 508-548-9600,

MVYRadio strives to entertain, inform, and educate using the power of music. Their loose format, dedicated DJs, and innate sense of what Islanders want to hear has kept it on the airwaves since 1983. WCAI’s programming is tailored to the needs and interests of our Cape and Islands community.

Elizabeth Cecil

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

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

Oak Bluffs Fireworks

Ocean Park, 
Oak Bluffs, 

People of all ages flock to the Vineyard during that special week in August when the iconic Ag Fair and popular Oak Bluffs Fireworks display occur. This summer, unfortunately, both have been canceled. But it gives us all the more reason to celebrate their triumphant return next year. Mark your calendars for the fair’s dates: August 19-22, 2021!