How to Spend Summer on Martha’s Vineyard, According to Island Insiders

Martha’s Vineyard has long been known as a summer hot spot for East Coasters looking to escape the city. But one town on the island, Oak Bluffs, has served as a beloved hideaway since the 1800s, drawing visitors with its gingerbread cottages, lively waterfront and history as a haven for generations of Black vacationers.

“Oak Bluffs is just one of those towns where you can be anybody,” Jarrett Campbell, a fourth-generation islander on the board of directors of The African American Heritage Trail of Martha’s Vineyard, told Chase Travel. “You can be rich and famous, or you can be a fisherman. It’s just accepting.”

That welcoming spirit, along with a growing food scene and a stacked calendar of seasonal events, has made Oak Bluffs one of the centers of the Vineyard’s summer magic. To help you plan your next trip to the island, we gathered recommendations from Campbell and two other Martha’s Vineyard insiders: Austin Bryant, a photographer behind the exhibition Where They Still Remain, who grew up spending summers in the Bluffs, and Lacey Williams, the chef and founder of Nyamnz Martha’s Vineyard.

The Main Attractions

Plan to spend an afternoon or two lounging at Inkwell Beach.

Inkwell Beach

This heavily frequented beach has “been a community meeting point forever,” Bryant says. Plan to get there early during the summer months, as perennial hot spots like Inkwell and State Beach tend to fill up quickly.

Looking for a more low-key spot? Take chef Williams’ advice and check out the Vineyard Preservation Trust website to find quieter alternative spots for a swim. “It might take a little bit of a hike to get to some of them, but they’re really great beaches,” she explained.

Circuit Avenue

This bustling street serves as “the main drag in Oak Bluffs,” according to Bryant. “It’s where all the stores, shops and restaurants are.” Circuit Avenue also provides access to most, if not all, of the sights the area has to offer, and it’s where you can pick up a classic Martha’s Vineyard crewneck as a souvenir.

The African American Heritage Trail of Martha’s Vineyard

If you’re more of a history buff, you’ll want to spend an afternoon or two following the 41 designated sites that make up The African American Heritage Trail. You can pull up a map and lead your group through the sites yourself, or follow Campbell’s advice and join one of the guided tours that pick up in Oak Bluffs. Expect stops in town to include the former home of Dorothy West, a Harlem Renaissance–era writer; Shearer Cottage, one of the first accommodations to host Black travelers; and The Gospel Tabernacle, a church that hosted the summer Oak Bluffs crowd for more than 20 years in the mid-20th century.

Flying Horses Carousel

Campbell regards the Flying Horses Carousel as a must-visit: It’s the oldest platform carousel in the country, with a past life that included a brief stint at Coney Island before it arrived in Oak Bluffs in 1884. “No matter how old you are, you’ll feel like a kid again,” he said, “especially if you have kids.” In the summer, it operates seven days a week.

Aquinnah Cultural Center

For a quiet escape, consider a day trip to Aquinnah, at the western end of the island. An ancestral homeland of the Wampanoag people, it’s surrounded by ocean and home to the Aquinnah Cultural Center, a museum that celebrates the tribe’s history and culture. “The island is more rural than people think,” says Bryant, whose photos exploring communities that have shaped the island for centuries were exhibited at the Martha’s Vineyard Museum in 2025. “Both Black and Indigenous people hold this island sacred, as a home. The Vineyard is a fun vacation spot, but there’s a history of why people revere the land.”

The Summer Social Calendar

While the Vineyard comes to life from May to early September, if you want to visit during its peak, plan your visit for August, and head to these events. After all, according to Campbell, more events now occur later in the summer, and “August is the new July.”

Grand Illumination

A summer tradition dating back to 1869, Grand Illumination night takes place on the third Wednesday of August each year. The evening starts at the open-air Tabernacle, near Oak Bluffs’ village of brightly painted gingerbread houses, where guests enjoy live music from the Vineyard Haven Band. After the sun sets, the event moves outdoors, where decorated paper lanterns are lit and hung from houses and trees.

Martha’s Vineyard African American Film Festival

For celebrity-spotting and first looks at films getting released over the next year, head to this annual nine-day showcase of both indie and big-budget projects, which takes place at the beginning of August in the Martha’s Vineyard Performing Arts Center.

Where to Stay

Explore playful design, jumbo-sized games and ocean-facing hammocks at Summercamp.

The Oak Bluffs hotel scene is steeped in history, with many properties in the neighborhood open and operating for two centuries. When it comes to choosing where to stay, location is essential, especially since parking space on the island is limited. These two hotels combine central locations with waterfront views, ensuring peak summer-on-the-Vineyard vibes.

Summercamp

Located across from the Oak Bluffs Harbor in central downtown, Summercamp is the largest oceanfront hotel in Martha’s Vineyard. Take a quick stroll through the property’s playfully designed lobby, and the inspiration behind its namesake is immediately clear from the large porch, game room and hanging rattan hammock chairs. The hotel’s 95 rooms are just as lively, with pops of teal and yellow; some even include bunk beds or a hanging king-size bed. If you’re traveling with pets, the hotel offers two dog-friendly rooms with private entrances. Most enticing of all, the hotel has 17 parking spots—a luxury hard to come by on the Vineyard.

The Morgan Hotel

Sandwiched between Circuit Avenue on one side and seven-acre Ocean Park on the other, The Morgan Hotel is an Oak Bluffs mainstay. The boutique property has just 14 rooms, and no two are alike, though all have Victorian-era details like vaulted ceilings, large French doors and a personal vanity. When it comes to getting outdoors, guests can enjoy lounging on the hotel’s enclosed porch after a day at the beach.

Where to Eat and Drink

Stop by BackDoor Donuts after hours for a late-night sweet treat.

From coastal classics like lobster rolls and pizza to Peruvian and Jamaican cuisine, you’ll find yourself spoiled for options, especially during the summer, when all restaurants are open for the season. To help you narrow down your must-eat list, we’ve compiled a list of top options from our local experts and friends at The Infatuation.

TigerHawk Sandwich Co.

This family-owned sandwich shop should be your first stop before heading to the beach or the park for a picnic. As for your go-to order, chef Williams suggests a chicken sandwich. (The Infatuation recommends ordering yours “tiger style,” meaning topped with sweet chili and miso mayo). The restaurant has just a few seats, so plan to take your order to go.

Biscuits

You’ll likely encounter a wait for your table at local favorite Biscuits, but the food and quick service will absolutely make up for it. Of course, you’ll enjoy dishes like chicken and biscuits with gravy here, but don’t discount the variety of pancakes and waffles or the cod cake Benedict.

Mad Martha’s

As Bryant puts it, ice cream on the Vineyard is “a big deal.” You’ll find plenty of shops across Oak Bluffs, but make room for a stop at Mad Martha’s, which serves inventive flavors like mud pie, maple walnut and a massive ice cream sandwich also known as the cookiewich. If you need more than a cone’s worth at a time, you can also snag pints from the freezer.

Nomans

According to The Infatuation, at Nomans, “the scene vastly outweighs the food,” meaning you can enjoy hot dogs and lobster rolls, but you’re really there for the ambience. When weather permits, arrive early to grab a seat outside for lawn games and live music alongside sips of Painkillers and mai tais.

The Pawnee House

This former hotel has evolved into a classic Vineyard restaurant known for its casual atmosphere and delicious food—the chicken pot pie and Korean short-rib tacos are crowd favorites during dinner service. “You have to make a reservation, but it’s really, really nice, and their food is amazing,” Williams recommends.

BackDoor Donuts

Originally opened in 1948, this Oak Bluffs staple serves fan-favorite flavors like Boston cream and glazed buttermilk. “At night, you can line up in the back and get really good doughnuts,” said Bryant, making it a must-stop for late-night sweets cravings. If you’re looking to try something besides a doughnut, Bryant insists you can’t go wrong with an apple fritter.