Best of the Vineyard 2022: 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 Charity Event: Taste of the Vineyard – Vineyard Preservation Trust

Dr. Daniel Fisher House lawn, 99 Main Street, Edgartown, 508-627-4440,

Runner-up: Christmas in Edgartown – Edgartown Board of Trade

Downtown Edgartown,

Maybe it’s the champagne talking, but there’s no better party than “The Taste,” and this year’s a big one with its return after a two-year Covid hiatus. Dancing, mingling, sampling appetizers, and making memories all benefit a good cause: preserving the Vineyard Preservation Trust’s historical Island landmarks. Christmas in Edgartown kicks off the holiday season with jolly events for both adults and children.

Best Family Activity: Flying Horses Carousel

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

Runner-up: Martha’s Vineyard Museum

151 Lagoon Pond Road, 508-627-4441,

Brass ring or no brass ring, everyone’s a winner at the Flying Horses, the nation’s oldest platform carousel. If there’s a line, consider loading up on popcorn, cotton candy, and lemonade from the tiny ticket counter. No trip to the Island would be complete without visiting the Martha’s Vineyard Museum. Current and permanent exhibits are all listed online, making it easy to plan ahead.

Best Live Band or Musician: Johnny Hoy and the Bluefish


Runner-up: Vineyard Sound


It only takes a couple bars to recognize the deep rich vocals and tunes of Johnny Hoy, Jeremy Berlin, Delanie Pickering, and Kevin Medeiros – the four-piece roots rock band with a bluesy jazz feel that can make even the most devout wallflowers swing their hips and tap their toes. The all-male a cappella group Vineyard Sound puts its own unique spin on covers such as “Walking in Memphis” and “Beyond the Sea.”

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,

With a prime location in downtown Oak Bluffs, the historic dive bar that is The Ritz is a standout spot for anyone who wants to hear a wide range of live performers. At Nomans, what’s more glorious than sitting outside with a beer and your buddies listening to Dave Alves or Blue Switch?

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

91 Edgartown–Vineyard Haven Road, Oak Bluffs, 508-645-9599,

The Martha’s Vineyard Film Center has everyone shouting, “Let’s go to the movies!” This single-screen cinema regularly shows a diverse mix of movies in all genres. The Vineyard’s Drive-In offers a new old-fashioned experience to Vineyarders.

Best Off-Season Event: Christmas in Edgartown – Edgartown Board of Trade

Downtown Edgartown,

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

Weigh Station, Dock Street, Edgartown,

No holiday bucket list is complete without attending Christmas in Edgartown, where each December a parade kicks off the season of holiday lights, local sales, and visits from a popular jolly guy in red. Come fall, the Island is hooked on great fishing and memories made during the Derby.

Best Performing Arts Organization: Martha’s Vineyard Playhouse

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

Runner-up: Vineyard Sound 866-846-7686,

An Island institution and perennial favorite, the Martha’s Vineyard Playhouse delivers a mix of staged readings, full productions, exhibits, classes, and more. Vineyard Sound supports the local scene with a jam-packed schedule of performances each summer, including impromptu concerts on the street.

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,

Maybe Blues at 8 with Bill Narkiewicz is your jam, or maybe you prefer Sunday morning jazz with Dave Kish. Everyone finds something to love on 88.7 – each year they take the top spot for radio. WCAI a day keeps the Cape and Islands informed all year long.

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

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

Runner-up: Grand Illumination Night

Trinity Park, Oak Bluffs, 508-693-0525 x14,

All roads lead to the Agricultural Fair in August, for good reason. There are baby barnyard animals to see, fried food to eat, draft horse shows and skillet throws to watch, and colorful rides to enjoy. The Martha’s Vineyard Camp Meeting Association calls Grand Illumination Night the crown jewel of the Camp Ground season.