Here in Oak Bluffs (known to many simply as “OB”) crowds flock to Circuit Avenue and the town’s bustling harbor, day and night. The busy marina, legendary carousel, quirky gift shops, and sweet-smelling ice cream parlors are much loved by day-trippers and seasonal visitors alike. After dark, a buzzing strip of bars and live music venues make Oak Bluffs the beating heart of the Island’s nightlife scene. 

The second smallest of the six Island towns geographically, Oak Bluffs is the largest in population year round and second during the summer season. Many of the homes in “Cottage City” – where the town began as a Methodist revival retreat in 1835 - are historically significant as Carpenter Gothic revival structures, America’s only original architecture. These Victorian-style, “gingerbread cottages” are listed by the Massachusetts Historic Commission, and the Campground itself is listed on the National Register of Historical Places. 

A diverse town, particularly during the summer, Oak Bluffs is a bastion of Native American, Portuguese, and Black history. Oak Bluffs will be nationally recognized by the Smithsonian Institute with an exhibit in the National Museum of African American History and Culture when it opens in 2015.

DON’T MISS:

1. Circuit Avenue
Always the business center of town, Circuit Avenue was named for the circular street designed by Robert Morris Copeland. One of the first buildings, the Arcade, was built in 1872 and still stands today (shared by The Locker Room and Sharky’s Cantina) at 32 Circuit Avenue. Bars, restaurants, gift shops, and ice cream parlors keep the town’s main thoroughfare lively from morning to night. 

2. Campground
The first Methodists camped in tents surrounding Wesleyan Park where services were held. As the years went by the tents became more permanent wood plank homes. Today, there are 300 of these colorful, delightful, and hand built private homes. Take a walking tour of the area or visit The Cottage Museum.

3. Tabernacle – Trinity Park
Surrounded by the lovely cottages and originally the site of a preacher’s stand, the Tabernacle, 100 feet high, 130 feet across, and seating more than 3,000, was built from wrought iron in 1879. On Illumination Night each August, hundreds of Japanese lanterns decorate the Tabernacle and the eaves of surrounding cottages in a celebration that traditionally marks the end of summer. The Tabernacle is listed in the National Register of Historic Places, and offers a number of cultural and musical events (and a Family Movie Night) throughout the summer season. Visit mvcma.org. 

4. Wesley Hotel

Built by A.G. Wesley in 1879 for the sum of $18,000, the hotel prospered until a November 1894 fire. Three days later, Wesley confessed to arson. He wanted to build “an even larger, more creditable hotel for the community.” The hotel rehired Wesley as a cook after he served three years in jail. This sole survivor of the large hotels once so prominent in Cottage City was remodeled in 1986.

5. Oak Bluffs Harbor

Once a swampy, landlocked pond called Lake Anthony, the harbor was opened to the ocean at the turn of the century and now holds as many as 500 boats at a time.  Home to fishing charters and boat tours, the harbor is the Island’s largest marina, and the boardwalk bustles with shops, restaurants, and live music. 

6. Flying Horses

The Flying Horses Carousel has been delighting generations of Island residents and visitors for over 130 years. Built in 1876 and moved from Coney Island in 1884, it is the oldest operating platform carousel in the country and is registered as a National Historical Landmark. There are 22 wooden horses with real horsehair tails — and of course, a brass ring. Catch it and win a free ride! Open Easter – Columbus Day. 

7. Ocean Park & The Bandstand
The beautiful 7-acre park at the entrance to town hosts the annual Oak Bluffs fireworks held each August and Sunday evening concerts from the 1880s bandstand. The houses surrounding the park – most built in the late 1800’s - reflect the more affluent families who came to Oak Bluffs. Perfect for picnics, kite-flying, or a post-ice cream stroll.  

8. Union Chapel
55 Narragansett Avenue. This octagonal chapel was designed by architect Samuel F. Pratt of Newport and built in 1871 as an inter- denominational summer church. Concerts and cultural events are held here throughout the summer. Union Chapel is owned and operated by the Martha's Vineyard Preservation Trust and is on the National Historic register.

9. Arts District
Located along Dukes County Avenue at the edge of the Campground, the Arts District is a concentration of galleries featuring fine art and photography as well as jewelry and clothing boutiques.