Facts:

The first inhabitants of Oak Bluffs were the Wampanoag people, who have lived on Martha’s Vineyard (Wampanoag name: Noepe) for approximately 10,000 years. The area was later settled by Europeans in 1642 and was part of Edgartown until 1880, when it was officially incorporated as Cottage City. The town re-incorporated in 1907 as Oak Bluffs.

Population: Approximately 4,527 people

Zip code: 02557

East Chop Lighthouse

OB is the abbreviated town initials and how it is often referred to by locals.

2025 Tax Rate: $7.37

Oak Bluffs has a total area of 26.0 square miles, of which, 7.4 square miles of it is land and 18.6 square miles of it (71.61%) is water.

One of the three down-Island towns (along with Edgarown and Vineyard Haven). Oak Bluffs is quite possible the busiest town for summer tourists, and is noted for its “gingerbread cottages” and other mid- to late-nineteenth-century historic buildings of “Carpenter-Gothic” style architecture.

Since since the eighteenth century, Oak Bluffs has been, and continues to be an historically important center of African American culture. West African slaves first arrived in the 1600s to work on farms belong to European settlers. In the late 19th century affluent African Americans bought summer homes in Oak Bluffs, and by the 1930s the town became the most exclusive destination for African American tourists. Well known residents include Dorothy West, Adam Clayton Powell Jr., Charles Shearer who built Shearer Cottage – the first inn for African American vacationers.

The Oak Bluffs Campgrounds was home to Methodist meetings held under tents and often on wood platforms, which eventually became the small gingerbread houses. The Tabernacle was built in the center of the meeting space, and in 2005 was recognized as a National Historic Landmark.

Downtown Oak Bluffs

Oak Bluffs has a lot to offer, Circuit Ave is the main shopping street framed at the entry by Giordano’s family owned restaurant since 1930 and the Island Theater, originally built in 1915. On this Main Street, you’ll find many restaurants from casual and fine dining to tacos and take-out eateries, coffee shops, stores, and bars including The Ritz, The Lampost and the Island House. Running parallel to Circuit Ave. is Kennebec Ave. with the Offshore Ale Company and Brew Pub, an Island Treasure.

in the center of town is the Flying Horse Carousel, America’s oldest platform carousel, now managed by the Vineyard Trust. Across from this is the Chowder Company and Loft game room for adults, with pool, darts, shuffle board and more.

Circuit Ave. Extension leads you to Oak Bluffs Harbor, and lots of great casual restaurants along the water, it’s a great spot to watch the boats in the harbor.

The Arts District is a short distance from the harbor up Dukes County Ave. along the outskirts of the Campground.

Out of Town

Beach Road leads you past Ocean Park and the Oak Bluffs bandstand – the location for the annual Oak Bluffs Fireworks. Continue on, and Beach Road will lead you to Edgartown.

East Chop is a peninsula that just out in to Vineyard Sound (There’s a West Chop too which is in Vineyard Haven). East Chop Lighthouse maintained by the MV Museum is on Telegraph Hill at the north of the chop. A residential area, with the private East Chop Beach Club.

Essentials: Farm Neck Golf Course, Police Department, Fire Station, Oak Bluffs Elementary School, Oak Bluffs Library, Viera Park, Niantic Park, Ocean Park

Events:

• Oak Bluffs Harbor Fest
  
  
• Oak Bluffs Open Flea Market
  
  
• Art District Art Strolls
  
  
• African American Film Festival
  
  
• Built on Stilts
  
  
• Grand Illumination Night
  
  
• Oak Bluffs Fireworks
  
  
• Martha’s Vineyard Wind Festival
  
  
• Tivoli Day

Beaches:

• Eastville Beach
  
  
• Oak Bluffs Town Beach

Trails:

• Trade Winds Preserve, a popular trail for dog walkers.
  
  
• Farm Pond Preserve
  
  
• Litte Duarte Pond Preserve
  
  Southern Woodlands Reservation