Walking Through Oak Bluffs' Gingerbread Cottages

Walking Martha’s Vineyard Gingerbread Cottages in Oak Bluffs

Here’s everything you need to know about Oak Bluffs’ Gingerbread cottages, its history, and thriving African American community in Martha’s Vineyard.
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Here’s everything you need to know about Oak Bluffs’ Gingerbread cottages in Martha’s Vineyard.

It didn’t take long for my mother and I to pick up the distinct contrast between Oak Bluffs and the surrounding Martha’s Vineyard towns. As we peddled our Nobnocket Boutique Inn bikes from Edgartown to Oak Bluffs, we immediately began to notice a change in pace, architecture, and culture. Oak Bluffs has been home to the African American community for over a century. The first African Americans to settle in Martha’s Vineyard were indentured servants, runaway slaves, and whalers. When slavery was finally abolished in the 18th and 19th century, the African American community settled into Oak Bluffs and made it their home. This settlement was just the start of a thriving and unique community on Martha’s Vineyard—the Oak Bluffs gingerbread cottages were at the heart of it.

By the mid-19th century Methodists had moved into the area. The Methodists were the ones who actually founded what is known today as Oak Bluffs. They used to hold summer camps out there and eventually built what came to be known as the gingerbread cottages you see today. The African American community had settled into Oak Bluffs due to it’s reliable employment in the whaling industry. Simultaneously, while the Methodists settled in, whale oil was no longer being used as a primary source of energy as it was displaced by other sources. That’s when a shift happened in Oak Bluffs and it transformed into a vacation spot and resort for middle and upper class African Americans.

Fun Fact: Former President Barack Obama has been an avid summer time visitor of Oak Bluffs and has been seen almost every summer since 2009 in the area.



When the Methodists settled in Oak Bluffs in the 1860s and 70s, they originally used to sleep in tents. As they settled in they did away with the tents and began to build colorful Victorian-like gingerbread cottages in a style known as Carpenter Gothic. These gingerbread cottages, which I think resemble more beautiful dollhouses, surrounded the town’s tabernacle, an outdoor cathedral where to this day ceremonies are still held. Out of the original 500 gingerbread cottages, 318 still remain. My mother and I spent a good hour walking in and out of the streets, fascinated by the colorful houses, unique architecture, and small stature. Wandering what is known as Cottage City is like walking into a fairy tale.



On the Friday we were visiting, a gathering was happening outside the tabernacle. There was a large communal barbecue and people out on picnic blankets listening to live music under the tabernacle. Apparently events are held here in the summer on a regular basis, the most popular being the community sing open to the public every Wednesday in July and August at 8PM.

One of the most famous annual events in Oak Bluffs happens the third Wednesday in August and is called the Grand Illumination Night. Residents of the gingerbread cottages light up their homes with Chinese lanterns and neighbors entertain one another by singing songs and the national anthem. This traditional event is something you won’t want to miss, so make sure to book your stay during this time of year in Oak Bluffs on Martha’s Vineyard!

>> Next: Menemsha, Martha’s Vineyard: An Unchanged Place

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