Oak Bluffs
First established in 1642, is a peaceful artistic town during the off season that blossoms into a bustling and vibrant community in the summer.
Probably the liveliest of towns, Oak Bluffs is known for the Gingerbread Cottages, the fantastic fishing pier and let us not forget the oldest carousel in the country, The Flying Horses.
Home to some of the best fishing charters on the island Oak Bluffs harbor is surrounded by restaurants and ice cream parlors that you can sit back and watch the day go by, all while enjoying fabulous food.
If you just have to get to the beach enjoy the idyllic Inkwell and State beach. If you want to get away from town center, head over to Island Alpaca and enjoy time cuddling these cute creatures.