Husband and wife team, Winston and Lisa Christie, have over 30 years of experience serving home-style food at Winston’s Kitchen in the Oak Bluffs area. This Black-owned restaurant uses the freshest ingredients to create breakfast sandwiches, Winston's Jamaican Jerk chicken, curry chicken, and even vegan dishes.

For over 20 years, Black family-owned and operated Biscuits restaurant has served delicious Southern-style breakfast and lunch menus with the finest seasonal ingredients. Dishes include classic favorites like the Western Omelet and Fried Chicken and Waffle, Pigs in a Biscuit, Lulu's Twisted Stuffed French Toast, and so much more.

The beloved year-round market and café Waterside Market in Vineyard Haven offers all-day breakfast, salads, and sandwiches. There’s also convenient online ordering and curbside pickup, outdoor seating, and delicious grab-and-go options. 

Black-women-owned food and wine hotspot Soul of Sonoma offers curated wine pairings, chef-inspired menus, and picturesque views for wine enthusiasts. Sample award-winning black- and women-owned wine, dine al fresco in the lush English Garden, or attend their annual Wine Festival.

Vineyard Caribbean Cuisine prides itself on serving the most authentic Jamaican dishes in Martha’s Vineyard prepared by Jamaica native Executive Chef Newton Waite. This Black-owned takeout restaurant serves delicious classics from Jerk chicken, curry goat and roti, oxtail, and Island Vanilla Rum Cake.

Bobby B’s Restaurant and Bakery serves classic American dishes, including Philly cheesesteaks, burgers, seafood, pizza, subs, and salads. With outdoor seating and participation in community events, it's a great spot to enjoy delicious food and engage with the locals.

Visitors learn profound stories about the African American Heritage Trail of Martha's Vineyard at over 30 dedicated sites. They highlight the unrecognized historical contributions of African descendants with a tour showcasing the island’s Black entrepreneurs and restaurateurs. 

Guided by a live and interactive remote host, this Venture Scavenger Hunt starts at a beloved local spot and ends with fun memories. Guests can walk or drive around the town to solve clues, take on bonus challenges, and have fun on themed excursions. 

This day trip with round-trip ferry and island tour goes from a scenic bus ride from Cape Cod to the beaches near Gay Head Cliffs in Aquinnah. Visitors get convenient hotel pick-up and drop-off from six local towns, complimentary bottled water, snacks, and island guide books.

Black-women-owned Caleen’s Day Spa offers a wide range of services including manicures and pedicures, waxing, massage, facial treatments, and body treatments. This local salon takes pride in its selection of locally made products, including natural and organic soaks, scrubs, oils, and butters, and nail polishes. 

For the traveler who loves theater, the Martha’s Vineyard Playhouse in Downtown Vineyard Haven is worth a visit. With year-round operations, visitors can enjoy contemporary and classic plays, including staged readings, workshops, and even world premieres.

The Island Alpaca Company of Martha's Vineyard offers unique self-guided walking tours and informative video presentations for all ages everyday. Visitors can take Alpaca yoga sessions with friendly alpacas or learn about alpaca care and living through educational workshops.

The Edgartown Lighthouse, managed by the Martha’s Vineyard Museum, has breathtaking views of Edgartown Harbor, Chappaquiddick, and Cape Cod. This historic landmark can also be rented for special occasions like proposals, weddings, or other family-friendly activities.

The community-inspired First Friday Artist Market in Vineyard Haven is a free event celebrating local art and culture every first Friday from June to October. There’s live art experiences, music performances, silent disco parties with DJs, and local food pop-ups.