Best Arts & Culture Organization: Martha’s Vineyard Museum

151 Lagoon Pond Road, Vineyard Haven, 508-627-4441, mvmuseum.org

Runner-up: Martha’s Vineyard Film Center

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

With funky exhibits, swanky events, and a steady drumbeat of programming, the Martha’s Vineyard Museum knows how to keep locals and tourists coming back. The Martha’s Vineyard Film Center’s sophisticated array of films has a certain je ne sais quoi. Streaming just can’t compete.

Best Charity Event: Taste of the Vineyard

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

Runner-up: 5K Run for Jabberwocky

14 Aero Avenue, Edgartown, 508-693-2339, campjabberwocky.org/5k

At the annual Taste of the Vineyard fundraiser, patrons sample delicious fare while dressed to the nines. Even better: the fun helps to keep iconic landmarks owned by the Vineyard Preservation Trust in top shape. For those who prefer sneakers to heels, the 5K Run for Jabberwocky will get you moving in support of summer programming for campers
with disabilities.

Best Family Activity: Flying Horses Carousel

15 Lake Avenue, Oak Bluffs, 508-693-9481, vineyardtrust.org

Runner-up: The Barn Bowl & Bistro

13 Uncas Avenue, Oak Bluffs, 508-696-9800, thebarnmv.com

Constructed in 1876 and operating on the Vineyard since 1884, the Flying Horses Carousel is still a blast for the whole family nearly a hundred and fifty years later. At the Barn Bowl & Bistro, good food and ten-pin bowling are the perfect combination. 

Best Live Band or Musician: Johnny Hoy and the Bluefish

508-696-3007, johnnyhoyandthebluefish.com

Runner-up: Vineyard Sound

866-846-7686, vineyardsound.org

They say if you hold a Vineyard conch shell up to your ear, you can hear the raucous rhythms of Johnny Hoy and the Bluefish. Okay, that’s not true, but Johnny Hoy’s blues might as well be woven into the Island’s fabric. Love music but hate instruments? The Vineyard Sound a capella group is the pastel-colored outfit for you.

Best Live Music Venue: The Ritz Cafe

4 Circuit Avenue, Oak Bluffs, 508-693-9851, theritzmv.com

Runner-up: Old Whaling Church

89 Main Street, Edgartown, 508-627-4442, vineyardtrust.com

The Ritz Cafe isn’t the only live music venue on the Island, but it wins points for both quality and consistency. No other venue hosts live music five nights a week, plus DJ sets. The Old Whaling Church pulls double-duty as a concert venue, hosting the likes of Nickel Creek and Jorma Kaukonen.

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: The Martha’s Vineyard Film Festival

Grange Hall, 1067 State Road, Second Floor, West Tisbury, 508-645-9599, tmvff.org

Featuring an eclectic mix of indie, international, and classic films, along with a rotating schedule of special events, the Martha’s Vineyard Film Center is the heart of the Island cinema scene. Each year, the Martha’s Vineyard Film Festival brings a new roster of unique films.

Best Off-Season Event: Christmas in Edgartown

Downtown Edgartown, christmasinedgartown.com

Runner-up: The Martha’s Vineyard Film Festival

Grange Hall, 1067 State Road, Second Floor, West Tisbury, 508-645-9599, tmvff.org

Edgartown looks especially nice when done-up with wreaths, bows, and a dusting of snow. Those who have attended Christmas in Edgartown seem to agree; the yuletide weekend wins Best Off-Season Event year after year. In the doldrums of March, the Martha’s Vineyard Film Festival brings the year’s buzziest movies to West Tisbury.

Best Radio Station: WMVY – 88.7 FM

489 State Road, West Tisbury, 508-693-5000,  mvyradio.org

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

3 Water Street, Woods Hole, 508-548-9600, capeandislands.org

WMVY has been faithfully broadcasting to the Vineyard and beyond since 1983 with its eclectic mix of folk, jazz, and blues. The station focuses on Island favorites and underappreciated artists. WCAI showcases regional and national news. 

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

35 Panhandle Road, West Tisbury, 508-693-9549, marthasvineyardagriculturalsociety.org

Runner-up: Beach Road Weekend

Veterans Memorial Park, Lagoon Pond Road, Vineyard Haven, beachroadweekend.com

Funnel cakes, spinning rides, and ceiling-scraping sunflowers can all be found at the annual Ag Fair in West Tisbury. Beach Road Weekend, the discontinued summer music festival, brought the likes of Patti Smith and Mumford & Sons to the Vineyard. For that we will always be grateful.