Oak Bluffs, Martha's Vineyard

A Short History of Oak Bluffs

Oak Bluffs started as a prayer meeting. In 1835 a group from the Methodist church in Edgartown pitched a ring of canvas tents in an oak grove near the water and called it Wesleyan Grove. The summer revival grew every year, and by 1860 tens of thousands of people were coming out for Big Sunday. Around then the families began swapping their tents for little wooden cottages, built to the same tall narrow footprint, and the local carpenters went to town on them with jigsaws. That is where the gingerbread comes from.

The turn that makes this a real town, and not just a religious camp, came in 1866. A group of investors formed the Oak Bluffs Land and Wharf Company, bought the farmland next to the campground, and hired a landscape architect named Robert Morris Copeland to lay out a whole planned resort around it, with curving streets, parks kept open to the sea, and lots for sale. It was one of the first vacation communities in the country built on purpose from nothing. For a while the place was actually called Cottage City. It took the name Oak Bluffs in 1907.

The other thing Oak Bluffs is known for is being, for well over a century, the most established African American summer resort in the country. African American families started buying property here in the 1890s, at a time when this was the only town on the island that would rent to them and one of very few resorts anywhere in America that would..

The first time I came to the Cape and Islands, this is where the boat let me off, and I walked up from the wharf into the middle of all that scrollwork and colored paint and did not really recover. I have been back most summers since. Edgartown is grander and Vineyard Haven is where the working boats are, but Oak Bluffs is the one that feels like a party the whole town is invited to.

The Campground and the Gingerbread Cottages

The campground is still there, and still its own thing. More than 300 of the cottages survive, packed tight on about 34 acres of narrow lanes and shared lawns, all of it owned and run by the Martha's Vineyard Camp Meeting Association. At the center is the Tabernacle, a huge open-sided iron and wood pavilion put up in 1879 that still holds Sunday services and summer concerts. There is a small Cottage Museum if you want the full history.

The cottages are private homes, so you look and do not knock, but the lanes are public and wandering them is the best free hour in town. The one night it truly comes alive is Illumination Night in August, when the residents hang the porches with Japanese paper lanterns and thousands of people file through in the dark. The date is not announced far in advance, on purpose, to keep the crowd down.

Ocean Park, the Flying Horses, and the Jaws Bridge

Copeland's plan left a wedge of green called Ocean Park, seven acres of it, open between the houses and the water, and it is the town's front lawn. There is a Victorian bandstand in the middle for the weekly summer concerts, and it is the spot everyone spreads out a blanket for the big fireworks show in August. On a clear evening the light on the ring of houses around it is worth the trip on its own.

Two more things. The Flying Horses Carousel, just up from the harbor, was built in 1876 and is the oldest operating platform carousel in the United States, a National Historic Landmark that still lets you reach for a brass ring as you go around. And out on Beach Road toward Edgartown is the little drawbridge everyone calls the Jaws Bridge, where the movie's first swimmer meets the shark. Kids jump off it into the channel all summer, and plenty of adults too.

Best Time to Visit Oak Bluffs

The town is built for summer and does not really hide it. July and August are when everything runs at once, the carousel and the arcades, the fireworks, the band concerts, Illumination Night, every restaurant open and every one of them with a wait. It is loud and crowded and completely itself, and worth seeing that way at least once.

My own favorite trips are the shoulders. In the middle of June, the water is coming up to temperature, the lines are short, and the cottages have their flower boxes going. September is even better, warm well into the month, with the day visitors gone. Winter is quiet to the point of shuttered, and the ferries pull back to Vineyard Haven, so time a trip out of season around what you actually want to be open.

Where to Eat and Drink in Oak Bluffs

The one I always start with is Coop de Ville, right on the harbor on Dockside. It has been there more than 35 years and it is the plainest kind of good, a full raw bar, a plate of fried clams, a basket of wings that has won things, and a beer, eaten at a picnic table while the boats come in. On a warm afternoon there is nowhere I would rather be.

For a proper dinner, Offshore Ale Company on Kennebec Avenue has been the island's only brewpub since 1997. The floor is covered in peanut shells, there is live music several nights a week, and the kitchen does wood-fired pizza and a good burger alongside the beer they brew in back. It is the most reliable dinner in town.

Giordano's, which everyone calls Gio's, has been run by the same family since 1930 and sits at the end of Circuit Avenue across from the carousel, under a neon PIZZA sign that is basically a town landmark. It was the Vineyard's first clam bar and it still does that and Neapolitan pizza and the old Italian American plates, no reservations, with a line down the block in August. For pizza to actually take to the beach, it is the move.

Late at night in summer, the back door of the Martha's Vineyard Gourmet Cafe and Bakery on Post Office Square opens for Back Door Donuts. The bakery has been tossing warm donuts out the back since the 1940s, and now there is a formal window and a formal line for the apple fritters, which come out huge and hot and slightly too greasy in the best way. Get one after dinner.

And when the weather turns, which it does, the Barn, Bowl and Bistro on Uncas Avenue is the answer. It is a real bowling alley with a real kitchen bolted on, so you can spend a grey afternoon rolling a few strings with a plate of good food and a drink at the table. It has saved more than one washed out afternoon for me.

If you want a drink and some noise, the Ritz Cafe at the top of Circuit Avenue is the oldest bar in town, a proper dive with live music most nights that a recent renovation did not manage to ruin.

One shopping note, since people ask. The Black Dog, with the black Labrador on every shirt, is a Vineyard institution, but the original tavern is over in Vineyard Haven on the harbor. There is a Black Dog General Store right on Circuit Avenue in Oak Bluffs if you need the sweatshirt without leaving town.

The Bottom Line

The bottom line: Oak Bluffs is a resort town more than 160 years old that was designed from the start to be looked at, and it holds up. Walk the gingerbread lanes, ride the carousel, sit on the Inkwell for a while, eat fried clams on the harbor, and stay for the fireworks. Come in June or September if you can pick.

Quick Facts

The essentials, at a glance.

Why This Fits an Austen Themed Guide

Oak Bluffs is Martha's Vineyard at its most performative, and it is laid out almost perfectly for a comedy of manners. The gingerbread cottages sit so close, porch facing porch across a shared lawn, that privacy is not really on offer. Every walk to the ice cream stand happens in front of an audience. Jane Austen built her sharpest novel, Emma, out of exactly this, a small dense village where everyone can see what everyone else is doing and the main sport is deciding who should marry whom. Coming off the quiet, dignified streets of Edgartown, where the whaling captains built their houses, into the pastel crush of Oak Bluffs is a lot like stepping out of an estate garden and onto a seaside promenade, which is a move Austen makes over and over, and always for the same reason, because the promenade is where the plot happens.

Continue Exploring the Islands

Nantucket is the sister island, 30 miles out, and the opposite of Oak Bluffs in almost every way, one grey shingled piece instead of a box of colored paint. A summer ferry connects the two right at Oak Bluffs Harbor. Up at the tip of Cape Cod, Provincetown is the other town at the end of the road in this part of the world, another place a fishing village turned itself into a stage.

Other Resort Towns Built for Society

If the invented resort angle is what pulls you, Newport, Rhode Island is the Gilded Age version of the same idea, a whole town given over to being seen. So is Lenox in the Berkshires, where the same families spent the other half of the summer. Down at the bottom of New Jersey, Cape May is the one that most literally matches the plot of Sanditon, a Victorian resort a land boom willed into being and a fire froze in place. Oak Bluffs earns its place on my running list of Austen settings and their Northeast doubles.

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