First of all, don’t ever call it Oaks Bluff, and only call it “The Bluffs” if you are feeling pretty confident about your status as an Islander of some sort or another.

The center of Oak Bluffs is easily the youngest, liveliest, friendliest town on the Island. Of course all the towns on Martha’s Vineyard are as friendly as towns can possibly be, but Oak Bluffs in the summer feels like a party. The main drag is crammed with bars and T-shirt shops, restaurants and funky old movie theaters.

Oak Bluffs is also a national architectural treasure, chock-a-block with the country’s finest collection of tiny Victorian gingerbread summer cottages painted every color except drab. It’s justifiably proud, too, of its history as one of the very few summer communities to welcome African-Americans almost since its founding as a Methodist revival campground in the 19th century. With a great beach facing Nantucket Sound and relatively easy access to South Beach in Edgartown, the only thing that can go wrong with a vacation in Oak Bluffs (besides finding parking) is…well, we can’t think of it.

Oak Bluffs Beaches

Eastville Beach

Marinelli Beach

Oak Bluffs Town Beach

"We like the big loop around Farm Pond and East Chop/Eastville. We park near the beach club, walk as far as the Nadler’s old house at the end of Eastville, and double back."

Alison Shaw

"I wake up and go to Tony’s Market and get my dark roast coffee and my chocolate chip scone. Then I drive down to the lagoon where I have my kayak. There’s no waves — the water’s like glass."

Geoff Rose

"I’d then go to Oak Bluffs and sit along Lagoon Pond to watch the traffic lazily cross the bridge. Once my toes start to wrinkle from sitting in the water, or I’ve lost interest in skipping rocks I’d head back up-Island to enjoy the comforts of home."

Lauren Petkus

Primer

A Brief History

Gingerbread House, Oak Bluffs, CampgroundFor two centuries after the arrival of the first English on Martha’s Vineyard in the 1640s, Oak Bluffs was a pleasant, but indistinguishable part of Edgartown, best known as a place to collect huckleberries. In the summer of 1835, however, nine canvas tents were pitched in a “grove of enormous oaks” behind East Chop, and members of the Edgartown Methodist congregation moved in and prayed, among other things, that it wouldn’t rain. They chose the site not only for its remote location and lovely trees, but in the hope of attracting fellow believers from Nantucket and the South Shore of Cape Cod.

It worked. By 1842 there were forty tents. By 1851 there were a hundred tents. By 1859 there were 250 tents. On “Big Sunday” in 1860, there were twelve thousand believers in the grove, attending 36 simultaneous prayer meetings. Perhaps most remarkably, from the very beginning, people of all colors and races were welcome in the grove.

By the 1870s some of the tents had transubstantiated into wood. Because of the layout of the campground, however, the new cottages weren’t much bigger than the tents they replaced, though they usually had a second floor, often with a balcony. Local carpenters worked through the winter creating ornate and unique trim that, along with the nearly universal use of Gothic and Romanesque arched windows, gives the tiny buildings their signature fairy-land look. Local businessmen knew a good thing when they saw it and developed the acres surrounding the campground similarly.

According to The New York Times in 1873:

No description can give a correct idea of this city of cottages, for such it is. The idea of the secular company was to furnish a residence at the sea-side, with all its beauties and comforts, at a cheap rate.  The city began with tents. Small cottages, cheap and plain, followed. Within four years, 1,000 cottages have been erected of all styles and costs, Swiss, Italian, Romanesque, and English, plain as a barn and gaudy as a Chinese pagoda. These cottages crowd on each other, and families must keep peace from necessity. They cost from $400 to $12,000.

In addition to the cottages and churches there were more than a dozen large hotels and restaurants, a massive croquet ground, miles of boardwalks, nightly concerts and dances, hundreds of bathhouses along the beach, and the Flying Horses Carousel, which was brought up from Coney Island.

Some things have changed, including the name of the town, which was originally incorporated as Cottage City in 1880 and renamed Oak Bluffs in 1907.  The road that ran from “Cottage City” to Edgartown is gone, as are the croquet grounds and the beach houses. But most of the town is remarkably intact, making it a national architectural treasure, chock-a-block with the country’s finest collection of tiny Victorian gingerbread summer cottages painted every color except drab. With a great beach facing Nantucket Sound and relatively easy access to South Beach in Edgartown, the only thing that can go wrong with a vacation in Oak Bluffs (besides finding parking) is…well, we can’t think of it.

“Settled” (as Edgartown): 1642

Incorporated as Cottage City: 1880

Incorporated as Oak Bluffs: 1907

Land Area: 7.4 square miles (19 km2)

Water Area: 18.6 square miles (48 km2)

Population: 4,527

Getting Around

Oak Bluffs is one of the easiest towns to get around on the Island. It’s one of two towns where ferries arrive in the summertime, and there is a wider variety of ferries to choose from. Once you do arrive, it’s a short stroll across the street to car, bike, moped rentals, and the town taxi stand. The Martha’s Vineyard Sightseeing Tours leave right from the dock as well, if you’re hungry to see the rest of the Island (you won’t miss these brightly painted buses). If you’re hungry for actual food, or shopping, or to stretch your legs, the commercial district of Circuit Ave, Ocean Park, and the Oak Bluffs Campgrounds are all just minutes away by foot.

Where to Stay

Oak Bluffs InnGingerbread cottages in the Campground are the holy grail of places to stay in Oak Bluffs. But if you don’t get your hands on one this year, there’s plenty of other beautiful rental homes, harbor side hotels, and friendly B&Bs in town. And when we say friendly, we mean the owner invites you to join his sunrise beach walk every day friendly.

Wherever you stay, you won’t be far from the beach, restaurants, and other things to do.

Milk, Cash, Etc.

Martha's Vineyard Savings Bank Oak BluffsUtility items in Oak Bluffs are all available in the downtown/Circuit Ave area. Reliable Market, a fully stocked grocery store, is right on the main strip. (So is Phillips Hardware). For drinks, snacks, and small grocery items, Jim’s Package Store and Our Market (both on the harbor) are good stops, with ATMS. There are plenty of other ATMs at the banks downtown, including the visitor information center, near the Flying Horses Carousel.

On Duke’s County Ave, just beyond the South end of Circuit, Tony’s Market has beer, wine, a few groceries, and a deli.

Gas is available at Jim’s, or at the Mobile station on Beach Road, heading towards Vineyard Haven.

If you have a medical emergency, you’re still in the right town. The Martha’s Vineyard Hospital is on Beach Road in Oak Bluffs, just before the draw bridge.

See & Do

Outdoors

Sengekontacket Pond, Fishing, SunsetMany people associate Oak Bluffs with nightlife and the hustle-bustle of Circuit Ave, but it’s actually a great outdoor town too. A huge portion of the State Forest, complete with hiking and (paved and unpaved) biking trails, spills into the southeast corner of Oak Bluffs. You’ll also find the Riverhead Disc Golf Course there (yes, golf with frisbees!) For fun on the water, a paddle (or windsurf, or kiteboard, around Sengekontacket Pond, fish from the new town pier, or simply hurl yourself off Big Bridge into the water. It’s sort of a rite of passage here.

Arts & Culture

Alison Shaw, Gallery, Arts DistrictOak Bluffs is home to the Arts District, a cool collection of galleries on and around Dukes County Ave that hosts lively art strolls in the summertime, often complete with wine, cheese, live music, and other treats. The arts scene is Oak Bluffs doesn’t stop there, though. Downtown, there is almost always live music, whether it’s at nightclubs like the Lampost and the Dive Bar, or one of the Island’s major music venues: Dreamland. Occasionally, you can catch an act playing outdoors in the Ocean Park gazebo or along the harbor. Whatever you’re looking for, you won’t have to look long in Oak Bluffs.

Shopping

Oak Bluffs ShoppingAlong Circuit Ave, and in the nearby Dukes County Ave Arts District, there’s plenty of shopping to be done, especially if you’re looking for a new work of art to take home. Even if you just want a cozy sweatshirt for a breezy evening, your options are endless. Handmade clothing and purses, delectable fudge, and a touch of the honky-tonk at Vineyard themed souvenir and t-shirt shops, you won’t leave Oak Bluffs empty handed.

Eat & Drink

Clams, Corn, FoodWe Islanders anxiously await that month in spring when the harbor side restaurants open their patios, the Circuit Ave staples reemerge, and we can finally get a slice to go of heavenly Gio’s pizza. We’re not complaining, though. We never get sick of Oak Bluffs’ year round restaurants, like a tour and a brew at Offshore Ale Co., award winning clam chowder at M.V. Chowder Company, or fried food perfection at the Ocean View. By the way, not only do most Oak Bluffs restaurants have their full liquor licenses, they have the drinks and nightlife to make it all worthwhile.