Oak Bluffs, Massachusetts (MA) Real Estate Sales and Vacation Rentals on Martha's Vineyard

Real Estate Agent with Sandpiper Realty, Inc.

Oak Bluffs on Martha's Vineyard, Massachusetts

<!-- End ImageReady Slices -->Oak Bluffs likes to celebrate the summer season – it's a classic beach town, filled with fun, music, and arcades. It has bars and shops and instant access to water and beaches. It has a spacious park, up on the bluff, overlooking the water. It has the Flying Horses, an old-fashioned carousel, and pizza carryout spots, tiny walk-in clam bars and a harbor that attracts hundreds of power boats.

And – in a Jekyll and Hyde moment that dates back a century and a half – it is home to the unique Martha's Vineyard Campmeeting Association, a collection of colorful "gingerbread" homes built as part of a Methodist summer retreat and now designated a National Historic Landmark.

It was with the Campmeeting Association that what locals call "OB" got its start. In 1835, when the land was all trees and forest and was a part of Edgartown, it was host to a two-or-three day Methodist religious revival meeting during the summer. The revival at Wesleyan Grove became an annual event, growing in popularity. At first, nine tents were pitched for the attendees. As the revivals got bigger – in 1858, 12,000 people attended the Sunday services – families started bringing their own tents and building often rough wooden platforms for them (there are examples of floors still supported by trees simply shorn of their limbs.) Finally houses – simple affairs, with inside walls that are also the outside walls, with no heat and tiny rooms but with elaborately decorated exteriors in a fantastic Carpenter Gothic style, were constructed on top of the platforms.

By 1879, an all-steel open-air Tabernacle, complete with stained glass and a stage, replaced the central tent. And though the revival meetings ceased long ago, the Tabernacle and houses remain today – doll-like summer homes colorfully painted, bringing back families who have enjoyed them for generations to spend a month or two with their summer friends. One curious note: although the families can buy or sell the homes, the land remains under ownership of the Campmeeting Association.

Meanwhile, just outside the secular Campgrounds, "Cottage City" (now called Oak Bluffs) grew up along Circuit Avenue. It was a celebration of summer's pleasures, sometimes referred to by the scandalized Methodists as "Sin City." There was a big seaside hotel (since burned down), and the Tivoli, a dance and recreation hall, also gone.

Among notable early summer visitors to Oak Bluffs were members of the African American community, who created one of the first black-oriented resort areas in the country. Historians have found that much of the land for these homes was bought during the depression by the housemaids who came with the white families for the summer. Later, as their children and grandchildren became some of the most prominent African American leaders in the country, they became host to famous black writers, politicians, judges and artists. In contrast to the tiny cheek-by-jowl homes of the Campgrounds, many of these houses, which occasionally come on the market but often stay in the same families, are big, sprawling homes with large yards and gorgeous architecture.

Another distinctive housing area in Oak Bluffs is East Chop, which begins at the private East Chop Beach Club and ascends in a triangle to Telegraph Hill, site of one of the Island's five lighthouses, and then back down to the public beach at Eastville Beach. The houses along the water are huge old mansions, many long held in the same families, with turrets and spires marking their mid 1800s architecture. More modest homes are on the interior of the Chop, away from the water, but many still with a hint of waterviews.

Today's Oak Bluffs has long stretches of beach – a town beach near the center of things, and Joseph A. Sylvia State Beach stretching eastward toward Edgartown. It's proximity to the beach (you can literally walk down to the end of Circuit Avenue and leap into the water) adds to its casualness. Bathing suits, some still dripping, often clothe those waiting to hop onto the Flying Horses Carousel, the nation's oldest operating platform carousel and a National Historical Landmark owned by the Martha's Vineyard Preservation Trust.

Circuit Avenue is the commercial heart of OB. It has ice cream and sunscreen, coffee stands and souvenir shops. It has Reliable Self-Serve Market, family owned and operated, and Giordano's Restaurant and Clam Bar, offering up family style meals since 1930. It has Back Door Doughnuts (on a summer's night, between 9 p.m. and 12:30 a.m., buy them fresh from the oven in the parking lot behind Reliable Market.) It has one of the four hardware stores on the Island – complete with lots of useful things like note cards and tiny beverage refrigerators.

Just at Circuit Avenue's end, before you leave the sidewalks that are flooded with people on summer nights, you'll see Union Chapel, a non-sectarian place of worship built in 1870. The chapel, owned by the Preservation Trust, features a unique octagonal design that rises into a soaring cupola and elaborate stained glass windows. The chapel, known for its excellent acoustics, is a favorite performance space, along with the much-larger Tabernacle in the campgrounds.

Public Beaches

  • Eastville Point Beach on the outer harbor side of Vineyard Haven, calm waves, clear water and sunset views.
  • Oak Bluffs Town Beach. Enormously popular, very narrow beach. Some parts have lifeguards.
  • Joseph A. Sylvia State Beach. Along Beach Road between Oak Bluffs and Edgartown, a great family beach.

Events in Oak Bluffs include band concerts biweekly in the summer at Ocean Park. In July, the aptly-named Monster Shark Festival brings hundreds of fishermen competing to haul in the biggest shark from the waters about the Vineyard – the 200 or three hundred pound sharks brought in hanging upside down from hoists jutting high into the air.

Each August, on Illumination Night, always a Wednesday, residents of the Campgrounds light their houses with hundreds of Japanese-style lanterns, and there is a final season-end celebration at the Tabernacle. Days later, the Island's end-of-summer fireworks celebration is held in Ocean Park, marking the end of the Vineyard's season. A final September fling called Tivoli Day has been a regular event for almost three decades, with the town blocking off Circuit Avenue and the merchants staging a shelf-clearing sidewalk sale.

Although Oak Bluffs throbs in the summer, it has become a very viable town in winter. There are a large number of restaurants that stay open, including the Island's only brewery, the Off-Shore Ale Company, housed in an old wooden building with high ceilings and many fishing and boating artifacts. Away from the shore, there are a number of more modest homes in the 8.7 mile square mile area of the town, where many of the 2,800 people who are residents of Oak Bluffs live. It has its own elementary school, with just over 400 children in grades pre-kindergarten through eighth grade. Its new library is a soaring, light-filled building completed a few years ago.

It is also home to three of the Island's most significant public institutions, the Martha's Vineyard Hospital, the Martha's Vineyard Regional High School, and Martha's Vineyard Community Services. With two dozen beds and an affiliation with Massachusetts General Hospital, the local health center offers acute care. The high school serves the entire Island, with about 800 students in grades 9 through 12. Community Services provides health and human services, including Head Start programs, home nursing care and support groups. A new YMCA, which will have a pool to be used by the high school and the public, is being built adjacent to the high school and Community Services.

The high school and hospital are two of the only regional facilities on the Island – all six towns have their own libraries, town governments, and fire and police departments, and all but Aquinnah have their own elementary schools.

Martha's Vineyard Transit Authority buses serve Oak Bluffs, stopping in Ocean Park just across from the Steamship Authority pier. There are also plenty of taxis available in the summer months when the ferries run. In those months, passenger ferries from Oak Bluffs serve New Bedford, Hyannis, Nantucket and Falmouth; and a Steamship Authority car ferry serves Woods Hole.


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Sharon Purdy

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