Best of the Vineyard 2021: Events and Entertainment

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

Best Charity Event: A Taste of the Vineyard – The Vineyard Trust

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

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

A Taste of the Vineyard must live large in voters’ hearts: it nabbed the top spot despite being cancelled the past two years due to the pandemic. Thankfully, organizers promise the rollicking party will be back in 2022. The 5K Run for Jabberwocky gets hearts pumping in support of the beloved summer camp.

Best Family Activity: Flying Horses Carousel

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

Runner-up: Island Alpaca Company

1 Head of the Pond Road, Oak Bluffs, 508-693-5554,

The Flying Horses isn’t just for kids – competing to get that coveted brass ring while the recorded Wurlitzer band organ plays will make anyone feel young again. Furry animals are on full display at Island Alpaca, where guests can get up close and personal with the happy herd.

Best Live Band or Musician: Johnny Hoy and the Bluefish


Runner-up: Vineyard Sound


Johnny Hoy specializes in blues music and getting people on the dance floor. Who better to help us dance the blues away from the year the music almost died? Look for him and his Bluefish at an Island bar, event, or wedding. The Vineyard Sound a capella group is known to turn street corners into venues with impromptu strolling concerts, as well as regularly scheduled performances.

Best Live Music Venue: The Ritz Cafe

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

Runner-up: Old Whaling Church

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

The Ritz offers big sound in a small space, the perfect combo for live music. Local bands such as the Black Eyed Susans and the Brothers McMahon keep the dive bar humming into the wee hours. The Old Whaling Church is a beautiful venue to enjoy classical music and visiting artists.

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,

What’s so great about the MV Film Center? Stellar programming, a huge screen, and seats so comfy they might just lull you to sleep if the films weren’t so well curated, for starters. Its international film festival in September is also a big hit. Entertainment Cinemas is your go-to for the latest blockbuster.

Best Off-Season Event: Christmas in Edgartown

Downtown Edgartown,

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

Dock Street, Edgartown,

Edgartown receives a winter makeover during the annual Christmas in Edgartown weekend each December. From a parade to photos with Santa, and plenty of holiday sales, there is something for every good boy and girl. During the Derby, fishermen take to the shore and sea in search of a winning fish.

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,

All across the country, it’s just the same old song selected by the same old payola algorithm. In a sea of corporate radio stations, wmvy stands out for its eclectic mix of tunes curated by friendly, Island-grown human DJs. wcai provides a mix of local news and public radio staples. Undoubtedly, the real winners are the Vineyard listeners.

Best Performing Arts Organization: Martha’s Vineyard Playhouse

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

Runner-up: Vineyard Sound


The beloved playhouse ensured the show went on this past year with a selection of streaming productions and online readings, salons, classes, and musical revues. As for its next great act, stay tuned. The Vineyard Sound boys never grow old and never grow up. The ever-changing members of the a capella group have been doo-wopping and shoo-bopping across the Island for nearly thirty summers.

Elizabeth Cecil

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,

Though the Ag Fair went virtual last year, it was still a summer highlight. There were pre-recorded craft demonstrations, a live stream of the tractor pull, and the hall and barn entries could be viewed online…blue ribbons and all! This summer, fair enthusiasts will be pleased to know that a Covid-safe version will take place August 19 to 22. Grand Illumination also took a hiatus last year, but that didn’t stop some Camp Ground cottages from decorating.