Best of the Vineyard 2023: Events and Entertainment

Without further ado, we give you...everything you need to know about events and entertainment on Martha’s Vineyard according to you.

Best Arts & Culture Organization: Featherstone Center for the Arts

30 Featherstone Lane, Oak Bluffs, 508-693-1850,

Runner-up: Martha’s Vineyard Film Center

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

At Featherstone Center for the Arts, an Island institution, you can take a class to expand your skills, enjoy an art exhibit, or rock out to live music during Musical Mondays. The Film Center offers multiple festivals throughout the year, plus rotating visual art exhibits in the lobby curated by Featherstone staff.

Best Charity Event: Christmas in Edgartown – Edgartown Board of Trade

Downtown Edgartown,

Runner-up: 5K and Fun Run for Jabberwocky – Camp Jabberwocky

14 Aero Avenue, Edgartown, 508-693-2339,

For more than forty years, the Edgartown Board of Trade has celebrated the Christmas season with a weekend of joyful events that raise thousands of dollars for Island charities and nonprofits. Whether you’re a serious sprinter or a laid-back stroller, the 5K and Fun Run for Jabberwocky benefits the longest-running summer camp for people with disabilities in the United States.

Best Family Activity: Flying Horses Carousel

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

Runner-up: Martha’s Vineyard Museum

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

You’re never too old to experience the excitement of catching the brass ring at the Flying Horses, the nation’s longest continually operating carousel. The horses are in fine form following a restoration project this past winter. The Martha’s Vineyard Museum’s permanent exhibits about Island history educate people of all ages through photographs and artifacts.

Best Live Band or Musician: Johnny Hoy and the Bluefish


Runner-up: The Dukes of Circuit Avenue


For more than thirty years, Johnny Hoy’s vocals have powered this blues and rock band to a special place in the history of Island music. Catch their shows Island-wide all year long. The Dukes are a big band delivering soul, pop, and jazz hits, all with the goal of getting the audience dancing.  

Best Live Music Venue: The Ritz Cafe

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

Runner-up: Nomans

15 Island Inn Road, Oak Bluffs, 508-338-2474,

It’s all about that bass you’re hearing from the Ritz – the number one spot for live tunes of all kinds, from 2Boys to DJ AP. At Nomans, you can tap your toes to live music while playing lawn games and chowing down on French fries.

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

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

Runner-up: The Vineyard’s Drive-In

111R Edgartown– Vineyard Haven Road, Oak Bluffs, 508-560-2134,

You can’t go wrong with a cozy movie night at the Martha’s Vineyard Film Center. The diverse mix of genres will make you forget all about your streaming services at home. Journey to the 1950s at the Vineyard’s Drive-In for an old-school movie-watching experience during the summer months.

Best Off-Season Event: Christmas in Edgartown

Downtown Edgartown,

Runner-up: Ladyfest

Circuit Avenue, Oak Bluffs,

Christmas in Edgartown concentrates the Island’s holiday cheer into one yuletide jamboree. A highlight is the parade and a special appearance from Santa Claus. Ladyfest, in Oak Bluffs, features female artists from on- and off- Island to support Martha’s Vineyard Community Services’ CONNECT to End Violence.

Best Radio Station: WMVY – 88.7 FM

489 State Road, West Tisbury, 508-693-5000,

Runner-up: WCAI Cape and Islands NPR – 90.1 FM

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

Broadcasting live from the Vineyard since 1983, WMVY serves up an eclectic mix of blues, jazz, and acoustic tunes with a focus on quality, underappreciated artists. This marks their fortieth year on air – no small feat. WCAI brings fresh programming and informative news stories from around the Cape and Islands region, courtesy of its studio in Woods Hole.

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

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

Runner-up: Beach Road Weekend

Veterans Memorial Park, Lagoon Pond Road, Vineyard Haven,

Four days of old-fashioned family fun with farm animals, a Ferris wheel, fabulous art, and fried everything make the Ag Fair the number one event of the summer. Since 2019, Beach Road Weekend has brought big festival vibes to the Island, with lineups featuring both national and local acts.