Black August in Martha’s Vineyard is always a vibe. Each year, thousands of beautiful melanated people make their way to the upscale Massachusetts island town of Oak Bluffs to live their best lives in one of the country’s most exclusive zip codes. 

From industry parties and soaking up sun on Inkwell Beach to the annual Martha’s Vineyard African American Film Fest, the entire month of August is literally one massive homecoming for all who visit.

As you map out your future Oak Bluffs and Martha’s Vineyard plans, here are 20+ Black-owned businesses for you to support during your trip.


For some of the best chicken and waffles in the area, make your way to Biscuits. Located in the heart of Oak Bluffs, this breakfast and brunch spot is the go-to place for your morning meals. 

Open for breakfast and lunch, Edgartown Diner serves up everything from breakfast platters to juicy burgers and fries. Oh, and you can’t forget a milkshake, too. The eatery is located in the same building as Edgartown Cinemas. Also owned by the same owner—Chef Ralston Francis—Flavors MV is a sit-down Caribbean restaurant that pays homage to Francis’ Jamaican roots. On the dinner menu you’ll find: jerk chicken, stuffed snapper, as well as raw shrimp and oysters sold by the half or full dozen. 

Chef Deon aka ‘The Three Island Chef’ splits his time and talents between Martha’s Vineyard, Anguilla, and Jamaica. Currently located within the VFW Kitchen, you can order Chef Deon’s famous island-style cooking for lunch and dinner. Or you can book him for any catering needs, too. Open Monday through Saturday, Vineyard Caribbean cooks up some of the island’s most authentic Caribbean dishes including: ackee and saltfish, oxtail, as well as stew peas. Like many others in the area, they also offer catering options, too.

Owned by Winston and Lisa Christie, Winston’s Kitchen is open for breakfast, lunch, and dinner on the Oak Bluffs harbor. The waterside eatery features specials that change each day as well as regular staples such as breakfast sandwiches on local Cape Cod bagels as well as fresh soups and subs. 


If you’ve seen photos of the iconic Victorian home known as the Narragansett House in Martha’s Vineyard, then you know it’s part of a trio of homes now owned by Inkwell Haven. All properties are Victorian style homes located in Oak Bluffs and are all within walking distance to the area’s most popular restaurants and attractions. 

Another iconic home, the historic Oak Bluffs Inn is situated in downtown Oak Bluffs. Only five-minutes away from the beach, you can spend your day on the sand before heading back for an evening of relaxation. 

The historic Inn at Shearer Cottage was opened over a century ago by Charles Shearer, the son of an enslaved woman. It became the go-to summer haven for upper and middle class families during times when Black travelers didn’t have many options for safe accommodation. It underwent renovations during the 2022 season and will reopen in 2023. 

If you’re looking for a little more space for your group, consider booking one of the Black-owned rental homes in the area. The Larrier House and Sea U on the Vineyard are all available for full rental. Just be sure to reserve as soon as possible because these homes book fast, especially during Black August. 


Legendary MV apparel company. Image: courtesy of Legendary MV.

Get in a little retail therapy between activities while on-island. For unique clothing items, check out SidelineSuperar StrikeLegendary MV and Island Life Studio. They all have you covered with last-minute needs or even comfortable athleisure for your trip back home. Lennox & Harvey is your go-to for beach, body, and home goods. 


For the men, if you need a fresh line-up before your Black August events, stop by Blair’s Barber Shop in Vineyard Haven across from Woodland Center. A regular cut is $25 and a lineup is only $15. Ladies, if you need to fit in a bit of self-care during your MV visit, head to Caleen’s Day Spa. The full-service spa specializes in facials, make-up, nail services and more. 

Art Galleries 

Art lovers, you’re in luck as well. There are several galleries in the area including: long time Cousen Rose GalleryKnowhere Art Gallery and Harry Seymore Gallery—which is only open by private appointment.