In need of a getaway at a destination where Black joy, legacy, and pride are celebrated this summer? Look no further than Oak Bluffs.
For generations, this Martha’s Vineyard enclave has been a treasured summertime retreat for Black families where beach days stretch long, traditions run deep, and joy moves freely. From the early 1900s, when Oak Bluffs stood out as one of the few coastal towns that welcomed Black vacationers and homeowners, to today’s buzzy mix of legacy homeowners, visiting celebrities, and first-timers discovering the magic, the town has held onto its charm while expanding its cultural footprint.
It’s appeared in shows like “Bel-Air” and Netflix’s “Forever,” had its own franchise on Bravo’s “Summer House,” and inspired a Ralph Lauren campaign. Through it all, it remains the kind of place where you might see the Obamas at the beach in the morning and catch a block party by nightfall.
Whether you’re looking for a slow-paced getaway by the beach, a girls’ trip, or planning a family vacation, we break down everything you need to know, from when to visit, where to stay, what to do, and more.
When is the best time to travel to Oak Bluffs?
Peak season is typically during summer, with a real uptick from mid-July through Labor Day, when the island is buzzing with energy. That’s when the Martha’s Vineyard African American Film Festival hits (early to mid-August), and when the beaches are packed with familiar faces and impromptu porch parties. For a quieter vibe, early June and post-Labor Day September can still offer gorgeous weather with fewer crowds.
Where should you stay?
Oak Bluffs is known for its picturesque coastal beach houses and historic gingerbread cottages. Many families book their vacation homes and cottages up to a year in advance, while others have been passed down for generations. There are also several boutique inns, like the historic Oak Bluffs Inn, Summer Camp Hotel, and the Pequot Hotel.
What is there to do?
The island offers plenty of easy-living summer activities. You could kick your day off with a morning at Inkwell Beach or take a walk or bike ride through the Campground, a neighborhood with stunning, vibrant, and colorful preserved Victorian cottages. The African American Heritage Trail, where you can learn about the island’s deep-rooted Black history, is a must. Other activities include browsing the art galleries in Edgartown and shopping at Black-owned businesses around Circuit Avenue.
For families, the Flying Horses Carousel, which has the bragging rights as the nation’s oldest, is another island must. The island also has kayaking, sailing, and miles of hiking trails to discover.
Major events and weekends
The Martha’s Vineyard African American Film Festival, currently underway, is the crown jewel of Black summer on the island. Founded in 2002, the festival brings filmmakers, celebrities, and storytellers alike from across the country to the island for a week of premieres, talks, and celebration. It also involves the legendary White Party.
Other major weekends include Fourth of July and the Oak Bluffs Fireworks in late August.
Food and entertainment
Foodies can rejoice. The island offers many options for coastal cuisine, including Mocha Mott’s for coffee and pastries; Nancy’s, where locals and celebrities alike like to dine for lunch; the Lookout Tavern, with its ocean views; or Back Door Donuts for a midnight snack. Other haunts include Red Cat Kitchen for dinner and the iconic dive bar The Ritz.
