Oak Bluffs , commonly known as OB, was the Vineyard’s first summer resort known for its high energy, day and night, with shopping, eating and entertainment for the whole family. Oak Bluffs is the island’s late night town. Ice cream, t-shirts, gift shops and unique boutiques abound on Circuit Ave and the Oak Bluffs Harbor. There are several choices for eating and shopping on the harbor - Nancy’s or Coop de Ville are some of the Island’s well known and favorites. Mad Martha’s homemade ice cream is a popular choice in all 3 towns. The infamous Back Door Donuts is not to be missed for the ultimate donut experience late into the night.
Oak Bluffs is home to Featherstone Center for the Arts , located down Barnes Rd. 3 miles from town center, where the arts are celebrated with classes, events, art openings, a weekly flea market, and evening picnics with live music on the grounds. As the historical Methodist Revival Campground (est. 1835) gave way to colorful gingerbread cottages from the original tents on wooden platforms so did the whaling industry give way to a vacation economy in Oak Bluffs. Originally known as Cottage City, many of the buildings are elaborately detailed Victorian Homes representing the unique style called Carpenter Gothic Revival. Oak Bluffs has always been a popular summer destination for affluent African Americans since the turn of the century, visit mvafricanamericanheritagetrail.org.
Unique to OB is the island’s only bowling alley, The Barn Bowling & Bistro. Tony’s Market offers one stop shopping with a complete grocery store as well as wine & beer. A visit to Oak Bluffs is not complete without a ride on the Flying Horses, moved from Coney Island in 1884, the oldest platform carousel in the country with wooden horses and real hair. If you catch the brass ring you’ve won a free ride!