Oak Bluffs is the liveliest of the three down-island towns and the most colourful — both literally, in its pastel gingerbread cottages, and atmospherically. It is the place to go for the harbour-side bars and ice-cream parlours, the Flying Horses Carousel, the Wesleyan Grove cottages, and the nineteenth-century Union Chapel at the head of Circuit Avenue.
Oak Bluffs has historically been the African-American summer community on the Vineyard, with deep roots in the Inkwell Beach neighbourhood and a Black Methodist tradition that goes back to the camp meetings of the 1830s. It is also the only town on the island where you can buy a drink — the other two are dry — which is part of why everyone ends up here at some point in the evening.