Known for its Victorian-era architectural treasures, Oak Bluffs on Martha's Vineyard blossomed in the 1800’s as a summer religious retreat. A stay would not be complete without a walking tour of the Methodist Camp Meeting Grounds (also known as Cottage City), an enclave of multi-colored gingerbread cottages with a grand open-air Tabernacle centrally built within Trinity Park.
The nation’s oldest continually-operating carousel is located in downtown Oak Bluffs, the Flying Horses, where you can have a try at catching the brass ring while riding to the tunes of calliope music. A lively downtown experience offers gift shopping, hand-dipped ice cream cones, and summer evenings along the boat harbor brimming with cultural cuisine and one of the best arts and music scenes on the island.
One of two ferry ports is located in Oak Bluffs, where you will be greeted by the Ocean Park Gazebo, surrounded by grand Victorian summer manor homes and sweeping views of the ocean. Beach-goers young and old will enjoy the quiet surf and calm, shallow waters of its expansive town beaches, while golfers will enjoy 18 holes of championship-caliber golf at semi-private Farm Neck Golf Club, overlooking Nantucket Sound. Summer rental offerings include Gingerbread cottages, harbor front homes, modern and traditional estates, and luxury waterfront homes.
Where to Stay in Oak Bluffs: 
Downtown/Parks District – walk to everything, the beach and harbor right at your doorstep.
Cottage City – a tightly-knit community of gingerbread cottages walking distance to town.
East Chop – shingle and Queen Anne style homes of historical significance, close to town.
Harthaven – a neighborhood of eclectic yet exclusive beach homes with a rich history.
Central/Lagoon Heights – residential enclaves of wonderful homes on the outskirts of town along the Lagoon Pond.
Sengekontacket – an enclave of modern and shingled homes with access to biking, kayaking, fishing and conservation areas
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Oak Bluffs Beaches:
Joseph Sylvia State Beach
Oak Bluffs Town Beach
Eastville Beach
