Dense, diverse, a town prone to fits, and home to Flying Horses Carousel (the oldest one operating in America), OB can swing from Pebble Beach (Farm Neck) to Bourbon Street (Circuit Avenue).
OB first established Martha’s Vineyard as a resort. Originally part of Edgartown, then incorporated as Cottage City, Oak Bluffs attracted Methodists by the thousands in the early 19th century. Later, tens of thousands came. They held open air religious meetings in a central “Camp Ground.” They gave in to Island fun too. After pitching tents for some years, they conceived a micro village of hundreds of eccentrically colorful gingerbread cottages. The gothic cottages surrounded a new open-air wrought iron Tabernacle that seated 3,000. Mandating racial tolerance, this community opened the Island to African Americans. Oak Bluffs became America’s first black resort.
The Campground cottages remain delightfully colorful, some stranger-than-fiction. The Tabernacle is a superb venue to see national acts, including Vineyarder Livingston Taylor. (Church on Sunday is still there, too.) The Oak Bluffs harbor hosts the Island’s largest marina. The course at Farm Neck runs along Sengekontacket pond and Vineyard Sound—ultra scenic. In town, check out top-tier wood-fire brick oven pizza and hand-drawn cask micro brews at Offshore Ale Co. on Kennebec Avenue. There’s something fun for everyone in OB.