Nestled on the enchanting island of Martha’s Vineyard, Oak Bluffs stands out as a cherished New England beach destination renowned for its vibrant gingerbread cottages and historic charm. Once established as a 19th-century Methodist retreat, this Massachusetts town has evolved into a cultural hub celebrated by generations of Black Americans and notable figures such as Adam Clayton Powell Jr., Henry Louis Gates Jr., and Barack Obama. The community's picturesque architecture, combined with its beaches, lighthouses, and lively downtown, draws visitors from all walks of life. Accessible via ferry or flight, Oak Bluffs offers a unique blend of history, natural beauty, and modern amenities.
In 1866, landscape architect Robert Morris Copeland designed what would become Cottage City—later renamed Oak Bluffs in 1907. This planned residential area emphasized pedestrian-friendly pathways and communal green spaces, but it is most famous for its Carpenter Gothic cottages, often referred to as "gingerbread houses." These ornate structures feature intricate woodwork, bold colors, and elaborate trims, earning them recognition as a National Historic Landmark. Under the stewardship of the Martha’s Vineyard Camp Meeting Association (MVCMA), over 300 of these iconic cottages remain intact alongside the Tabernacle, an open-air pavilion that once hosted gatherings of up to 20,000 people. Visitors can explore these treasures independently or join guided MVCMA tours during peak summer months.
Beyond its architectural marvels, Oak Bluffs boasts several inviting beaches. Joseph Sylvia State Beach stretches two miles along the coastline, while Eastville Beach provides access near Vineyard Haven. For convenience, Oak Bluffs Town Beach sits close to the ferry terminal, harbor, and downtown attractions. Among its notable sections is Inkwell Beach, historically favored by African American families and recognized as part of the Martha’s Vineyard African American Heritage Trail. This trail features 41 sites highlighting the island’s deep connections to Black history and culture.
Activities abound in Oak Bluffs, catering to diverse interests. Boating enthusiasts may enjoy sailing or fishing excursions, while those seeking land-based entertainment can stroll through Circuit Avenue, where boutiques, eateries, and bars await. Golfers might tee off at Farm Neck Golf Course, frequented by celebrities like President Obama and filmmaker Spike Lee. Art lovers will appreciate Featherstone Center for the Arts, offering engaging classes and exhibitions. Families visiting with children shouldn’t miss America’s oldest platform carousel, the Flying Horses Carousel, relocated to Oak Bluffs after originating in Coney Island, New York.
Accommodations in Oak Bluffs range from historic hotels to contemporary inns. Among TripAdvisor’s top-rated options is the Pequot Hotel, a charming property adorned with gingerbread trim and boasting 32 rooms starting at approximately $246 per night, including breakfast and parking. Nearby, Summercamp offers expansive views of the harbor across its 95 rooms, complete with recreational games like Twister and Ping-Pong, charging around $342 nightly. Rounding out the list, the Morgan Hotel delivers water vistas within its 14 cozy rooms featuring dormers and vaulted ceilings, priced similarly in the $300 range.
Oak Bluffs exemplifies the perfect balance between tradition and innovation, making it an ideal getaway for travelers eager to immerse themselves in stunning scenery, rich heritage, and welcoming hospitality. Whether exploring its storied past or enjoying its vibrant present, this quaint yet dynamic locale promises unforgettable experiences for every visitor.