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Oak Bluffs: The Victorian Village

Oak Bluffs Harbor is well protected and a favorite of the powerboater.
Oak Bluffs is a charming town that was settled in the later 1800s, has many Victorian "cottages", and the oldest merry-go-round in the country (1876) - grab the brass ring and get a free spin. The 20 hand-carved horses of the Flying Horses Carousel have glass eyes and real horsehair manes and tails. There are few sailboats in the harbor as this destination is a favorite of the power boater; Oak Bluffs Marina, the largest on the island, provides lots of amenities, including harborwide WiFi.

Oak Bluffs is NOT a quiet harbor. Nevertheless, it can be a great stop especially with kids or when you need easy access to shore, civilization, food, etc. It has the feeling of a carnival town, with ice creams shops, bakeries, pizza palaces, saloons, restaurants, pubs, fudge shops, and more. A block to the west is the serenity of Trinity Park, home to more than 300 Victorian gingerbread cottages with brightly painted trim, and bursting gardens.

Islanders refer to Oak Bluffs as "Sin City", having started out ironically as a Methodist revival camground. During the Civil War it evolved into a Victorian resort town for middle income vacationers. The Sin City reference is to the fact that Oak Bluffs is the entertainment center on the Vineyard, with pubs and clubs on Circuit Avenue offering live music every night of the week. Ocean Park provides free concerts every other Sunday night in July and August.

Getting there

Approaching Oak Bluffs
Entrance to the small harbor is through a narrow inlet a half mile east of the East Chop Lighthouse. The harbormaster maintains the marina, with bathhouse, slips, and mooring. Moorings are first-come first serve, but slips can be reserved in advance. Rafting of up to three vessels on a mooring is managed by the harbormaster. Typically boats leave mid morning and moorings are plentiful til 1300. After that you may have to raft with others (ie, you can be tied up to someone you don't know nor want to be with or make new friends!) or the place may be full. This harbor is open to the northeast. In a blow from the NE/E it can be very rocky. Mandatory rafting is required if needed.

The access to town is great. Groceries, general store, liquor shop, bars, ice at Nancy's (at end of dinghy dock), restaurants, movies, arcade, "gingerbread houses", shopping, military surplus, access to bus service for the entire island, bike rentals, etc, all are within easy reach of the harbor. There is a quiet beach at the mouth of the harbor and a popular public beach three block east.

Related Links

  Oak Bluffs
  Oak Bluffs Marina VHF ch 71
  Farm Neck Golf Club 508-693-3057
  Felix Neck Wildlife Sanctuary 508-627-4850

Ferries to Oak Bluffs

  Inns - Dockside and Oak House
  Click here to view a street map of Oak Bluffs (large file).
  For a walking tour of Oak Bluffs, please click here to view the Vineyard Gazette.
  A second walking tour as provided by the Best Read Guide can be found by clicking here.


Click here for a larger view.

East Chop Light on Telegraph Hill near Oak Bluffs

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