Martha’s Vineyard, All Year Long: A Love Letter to Every Season

When the Martha’s Vineyard African American Film Festival began in 2002, it showed 10 films in a hotel conference room; today it is a festival that is eligible for consideration for an Oscar and which, each August, occupies the Martha’s Vineyard Performing Arts Centre in Edgartown for nine days, showing premieres, holding panels and having after-parties, and attracting filmmakers and other industry figures from all over the country.

Illumination Night in August at Oak Bluffs Campground has a 155-year-old tradition: once a year, thousands of paper lanterns are lit after dark, illuminating the gingerbread cottages and transforming the entire neighborhood into a bright, hand-painted display. The event takes place in mid-August, so it’s advisable to find a spot on the campground green well before dusk.

At Farm Neck Golf & Tennis Club, from spring to fall, the tee times get booked up as soon as the weather changes, so you should phone as soon as your dates have been decided. It has accommodated a sitting U.S. president for more than one of his summer visits, and the fairways extend towards Nantucket Sound, offering views so good as to make your swing slow down.

The Aquinnah Cliffs Overlook is open all year. The westernmost point of Martha’s Vineyard rises in bands of red, white, and gray clay above the Atlantic and is on land owned by the Aquinnah Wampanoag; enjoying the sunset here, whatever the month, is one of the best reasons to drive up the island.

The hike at the Menemsha Hills Reservation is available year-round. The Brickyard Trail in Chilmark is a moderate 3.1-mile out-and-back trail with a gain of 321 feet, leading past the ruins of a 19th-century brickyard and then down to a broad, rocky shoreline. Allow up to an hour and a half for the hike, and visit during the off-season if you want the trail entirely to yourself.

Morning yoga is held at Inkwell Beach during the summer. In July, it is on Thursdays and Sundays at 8 a.m., but in August it is every day. Those who rise early can also take part in the 7:30 a.m. polar bear plunge, a beautiful experience centered on the community, and a great way to begin the day.

You can bike around the island all year round, with the best time being from spring through fall. Sun 'n Fun, All Star Vineyard Bike Rentals, and Pedego’s electric bikes make it easy to travel around without having to use a car. Paved bike paths on the island link together Oak Bluffs, Vineyard Haven, and Edgartown, so a single bike rental will take you through all three towns during the afternoon.

Jubilee MV operates seasonally from May through October. The boutique, located on Circuit Avenue, is owned by Kahina Van Dyke, the Black woman entrepreneur who is also the proprietor of Oak Bluffs’ Inkwell Beach House, the Narragansett House, and Dunmere by the Sea. Jubilee features handcrafted items, jewelry, and vintage goods from independent designers throughout the diaspora and serves as the home base for the Jubilee MV podcast. If you time your visit well, you may see a live recording in the shop.

On Circuit Avenue, you can shop at Black-owned businesses both year-round and during seasonal hours. The Circuit Avenue area in Oak Bluffs is home to some of the island’s most significant Black-run businesses. C’est La Vie has been selling Vineyard souvenirs and items associated with the Divine Nine at 51 Circuit Ave for many years. Bee Blunt, a brand rooted in heritage and lifestyle, established its reputation through pop-up events before opening a permanent studio store on Juneteenth.

Nancy’s, which has been in family hands since 1960 and is situated directly on the harbor in Oak Bluffs, offers a simple seafood menu, a full sushi bar, and a deck from which you can see the boats coming in at eye level.

The Lookout Tavern is a simple bar on Seaview Avenue that serves some of the best fried clams on the island and has a deck perfectly positioned to watch the ferries come in.

Chef Ting opened Black Joy Kitchen, a restaurant in Oak Bluffs with 79 seats, in 2025, with the aim of featuring food from across the Black diaspora, including West African stews, Gullah rice traditions, and dishes from the Caribbean and South America, all of which are designed to be shared around the table.

Biscuits are a breakfast staple at Oak Bluffs, based precisely on what the name suggests: warm biscuits made from scratch, either topped with a lot of gravy or arranged on a proper Southern-style plate. Prepare to wait in line during high season.

Vineyard Caribbean Cuisine is a takeout restaurant owned by Black people in Oak Bluffs that offers some of the most authentic Jamaican food on the island, including jerk chicken and oxtail.

Fat Ronnie’s owner, Ronnie Faust, is from a family of five generations of butchers, a fact evident in each of the thick, never-frozen Angus patties at this burger bar in Oak Bluffs. Although the concept has now been introduced in New York City, the original restaurant is still the one worth the journey.

The Inkwell Beach Club is a coastal gathering place located right by Inkwell Beach, designed for staying over a drink with a view rather than for rushing through a meal.

Atria is located in a 19th-century sea captain’s house in Edgartown and offers refined New American food in an elegant dining room as well as a tented patio, which has hosted island celebrations since 2000.

The Pelican Club, the open-air restaurant at the Faraway Hotel in Edgartown, was designed for warm nights, offering fresh sashimi, vibrant ceviches, and a mezcal menu so extensive it would warrant a second and third round.

19 Raw is a stunning raw bar situated just off Main Street in Edgartown, opened by Chef Joe Monteiro in 2017, and remains one of the best spots on the island if you want to sample a dozen oysters with a cold drink.