Inside Martha's Vineyard's exclusive Oak Bluffs community — which boasts hundreds of adorable gingerbread cottages and is frequented by guests like Barack Obama

Darren McCollester / Stringer / Getty ImagesBarack Obama and his family are known to frequent Oak Bluffs.
  • Oak Bluffs, Massachusetts is one of the six towns located on Martha’s Vineyard.
  • The community boasts a cluster of cheerful and iconic gingerbread cottages.
  • It’s also one of Barack Obama‘s favourite vacations spots.

Oak Bluffs, Massachusetts is a town as vivid as it is historic.

One of the six towns on Martha’s Vineyard, Oak Bluffs is home to a string of colourful cottages, a bustling marina, and a picturesque downtown.

No wonder it’s one of former president Barack Obama‘s favourite vacation spots.

Here’s a look inside the community:


The town of Oak Bluffs, Massachusetts is situated on the northeastern shore of Martha’s Vineyard. It was first incorporated in 1880, and received its current name in 1907.

John Phelan/Wikimedia CommonsOak Bluffs, Massachusetts.

Source: Annals of Oak Bluffs, Oak Bluffs


Before Europeans settled on the island in 1642, the Wampanoag tribe occupied the area that would become known as Oak Bluffs.They called the swampy site “Ogkeshkuppe” — or “the wet or damp thicket.”

Source: Annals of Oak Bluffs


Today, the town is known for its distinctive and colourful gingerbread houses, its large marina, and its decades-old African American community.

Source: Oak Bluffs


According to Country Living, there are 318 gingerbread cottages in Oak Bluffs, out of an original group of 500.

Michele Schaffer/Wikimedia CommonsGingerbread cottages in Oak Bluffs, Massachusetts.

Source: Country Living


Before they were considered highly desirable real estate in an exclusive resort time, the cluster of cottages made up a Methodist summer camp.

Source: Country Living


Congregants had summered in tents, which were replaced with colourful abodes in the 1860s and 1870s.

Win McNamee / Getty ImagesGingerbread cottages in Oak Bluffs, Massachusetts.

Source: Country Living


The architectural style — which looks a bit like something out of a Victorian storybook — is known as “Carpenter Gothic.”

Source: Annals of Oak Bluffs, “Sightseeking: Clues to the Landscape History of New England


The gingerbread houses are now the site of a luminous Martha’s Vineyard tradition that dates back to 1869: Grand Illumination Night.

Source: Martha’s Vineyard, Vineyard Gazette


On the third Wednesday of August, residents of the cottages decorate their homes with Chinese lanterns and neighbours regale one another with songs like “In the Gold Old Summer Time” and the national anthem, according to the Vineyard Gazette.

Source: Martha’s Vineyard, Vineyard Gazette


The gingerbread cottages make up some of Martha’s Vineyard’s most iconic structures. Coldwell Banker listed one such cottage for $US525,000.

Elkman / Wikimedia CommonsGingerbread cottages in Oak Bluffs, Massachusetts.

Source: Country Living, Coldwell Banker


Oak Bluffs boasts Martha’s Vineyard’s largest marina, which sidles up against the gingerbread cottages. The town’s small harbour also features ferries from Nantucket, Rhode Island, and Falmouth.

Andrewrabbott/Wikimedia CommonsThe harbour of Oak Bluffs, Massachusetts.

Source: Martha’s Vineyard, Oak Bluffs Marina


Visitors without boats can make a splash at one of the town’s four public beaches.

Win McNamee/Getty Images

Source: Frommer’s


Oak Bluffs is also home to the historic East Chop Light, one of five lighthouses in Martha’s Vineyard. The lighthouse was first built in 1878.

Source: Martha’s Vineyard Museum


The Flying Horses Carousel, which was originally based in Coney Island before it was moved in the late 19th century, is one of the main attractions in Oak Bluffs. Catching the brass ring will win you a free ride on what the Vineyard Gazette described as “the oldest operating platform carousel in the country.”

Source: Vineyard Gazette


Oak Bluffs also features a cavalcade of galleries, boutiques, bars, and restaurants.

Source: Vineyard Gazette


Oak Bluffs also features Ocean Park and its historic bandstand, which was built in the 1880s. Today, the park is the site of the town’s annual fireworks show.

Source: Vineyard Gazette


The history of Oak Bluffs contrasts sharply with other towns on Martha’s Vineyard in that it has also been home to a thriving African American community since the 1800s.

Win McNamee/Getty Images

Source: CBS, The New York Times


Freed slaves settled in the area in the 1700s. In the latter part of the following century, African American vacationers were welcomed in Oak Bluffs, even as other communities on the island barred them from visiting.

Matthew Healey-Pool/Getty ImagesPhotographers document Barack Obama’s trip to Oak Bluffs, Massachusetts.

Source: CBS, The New York Times


As a result, many luminaries in the African American community have visited or lived in Oak Bluffs, from singer Ethel Waters to entrepreneur Madam C. J. Walker to explorer Matthew Henson.

Darren McCollester / Stringer / Getty ImagesCrowds gather in Oak Bluffs, Massachusetts to greet former US president Barack Obama.

Source: CBS, The New York Times


Not to mention former US president Barack Obama, who has frequently vacationed in Oak Bluffs with his family. To this day, the ex-president causes a stir when he visits various Oak Bluffs eateries.

Matthew Healey-Pool/Getty ImagesBarack Obama golfs in Oak Bluffs, Massachusetts.

Source: CBS


Out of all the towns on Martha’s Vineyard, Oak Bluffs has the biggest year-round population on the island. According to the Martha’s Vineyard Commission, Oak Bluffs boasts 16,814 year-long residents.

Source: Martha’s Vineyard Commission


The commission estimated that the median household income of people between between 25 and 44 was $US96,543.

Source: Martha’s Vineyard Commission


As of 2016, the average cost of a single family home was $US644,500, which the commission said was still the “lowest median sales price for single-family homes” on Martha’s Vineyard.

Source: Martha’s Vineyard Commission


The commission summed up bluntly: “If you don’t already own a home here, you probably can’t afford one now.”

Source: Martha’s Vineyard Commission

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