Oak Bluffs

An absolute hotspot on the island.

The Flying Horses Carousel is the oldest operating platform carousel in America. It was moved to MV in the 1880s from NYC. Incredible history. Check out the hundreds of whimsical gingerbread houses.

Oak Bluffs boasts the largest marina, which sidles up against the gingerbread cottages. The town's small harbor also features ferries from Nantucket, Rhode Island, and Falmouth.

And say hi to Obama, a frequent visitor.