Nowhere else in the world looks quite like the seaside village of Oak Bluffs, which grew from a Methodist revival camp into an African American summer enclave. In the 19th century, minister Thomas Mayhew founded a summer camp for Methodists. As pilgrims flocked here to hear religious speakers, many of them turned their tents into more permanent structures.
Now the town common overlooking the beach is surrounded by literally hundreds of gingerbread cottages—miniature Victorians hung with decorative woodwork icing and capped with towers and turrets. Every night during the summer months, romantics bring their beach blankets and white wine to sit around the gazebo and watch the sun douse itself in the harbor.
Oak Bluffs has always had a more festive attitude than the rest of the island, dating back from the amusements and theaters founded to entertain revivalists. The Flying Horses Carousel (Oak Bluffs Ave., Oak Bluffs, 508/693-9481, 10 a.m.–10 p.m. Sat.–Sun. Easter–early May, 10 a.m.–10 p.m. daily early May–mid-Oct., $1.50) is still the oldest operating carousel in the United States. During summer months, throngs of children wait to ride one of 20 carved wooden horses and take turns grabbing for the brass ring.
The town is also refreshingly multicultural compared to the rest of Martha’s Vineyard  and is home to a large African American community, particularly during the summer months when wealthy vacationers descend on the island. Many well-known African American celebrities have made their summer homes here, including Vernon Jordan and Spike Lee.