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‘Summer House: Martha’s Vineyard: 5 ‘Must Hit’ Spots in Oak Bluffs

The 'Summer House: Martha's Vineyard' cast is headed to Oak Bluffs. Here are a few fun things to do in this town.

by Gina Ragusa

Published on April 30, 2023

2 min read

Bravo’s new spinoff, Summer House: Martha’s Vineyard promises the usual drama and hookups, but the series will also spotlight the historic island.

The 12 friends will spend plenty of time in various towns on the island. But the rich history of Oak Bluffs is special. Known as a top spot for Black vacationers, Oak Bluffs is home to the adorable gingerbread cottages, the historic Flying Horses carousel, and an iconic harbor that has one of President Barack Obama’s favorite restaurants.

Here are 5 hot spots in Oak Bluffs:

Inkwell Beach

The Oak Bluffs town beach was given the moniker of “Inkwell Beach” in the late nineteenth century because it was a popular beach frequented by Black vacationers. The original name was pejoratively given by white residents, but it later became an emblem of pride. Several merchants lining the main street, Circuit Avenue sell Inkwell merchandise.

Pink gingerbread cottage in Oak Bluffs — Gingerbread Cottage in Oak Bluffs, MA on Martha’s Vineyard |Jonathan Wiggs/The Boston Globe via Getty Images

Plus, the 1994 film The Inkwell, followed a Black family as they traveled to Martha’s Vineyard in the mid-’70s to visit their affluent family who owned a home on the island.

Oak Bluffs Harbor (and Nancy’s Restaurant)

The Oak Bluffs Harbor definitely has a party vibe as boaters can anchor near the liveliest bars and restaurants on the island. The small seaside port is known for its party scene, especially on the rooftop at Nancy’s, a restaurant that is a personal favorite of President Obama.

The Obama family always stopped at Nancy’s and later daughter Sasha worked at the restaurant. She went by the name Natasha while working at the to-go window, flanked by security. Some employees didn’t realize they were working with the first daughter.

“She’s been working downstairs at takeout,” a server told the Boston Herald. “We were wondering why there were six people helping this girl, but then we found out who it was.”

Gingerbread Cottages and Campground

Oak Bluffs is known for its charming gingerbread cottages and scenic campgrounds. Originally designed as a religious getaway in 1835, a cluster of brightly painted gingerbread homes sprung up in the area between 1859 and 1864.

The campgrounds encircle the Tabernacle, an open-air community gathering spot, built in 1879. Today the spot is used for performances and community sing-a-longs.

Flying Horses Carousel

Hop on a horse and grab the brass ring to win a free ride! The Flying Horses Carousel is the oldest in the nation. Built in 1876 by Charles Dare of New York Carousel Manufacturing, it is only one of two in existence.

The carousel’s brightly painted horses and ornate picturesque designs, are an island favorite for any age group. Now owned by the Vineyard Preservation Trust, the carousel is maintained and preserved by local volunteers who paint and help to retain the carousel’s enduring charm every year.

Oak Bluffs events

In addition to a few must-see landmarks, Oak Bluffs hosts a few traditional summer festivals. Grand Illumination Night in August started in 1869 and the tradition lives on today. The homes and gingerbread cottages display illuminated Chinese lanterns at night. And the community gathers for a sing-a-long in the Tabenacle.

Oak Bluffs also has an annual fireworks display in August. Celebrants can bring a blanket, chairs and snacks to Ocean Park for a night of “oohs” and “ahhs.”

Catch Summer House: Martha’s Vineyard on May 7 at 9 p.m. ET on Bravo.