There’s no shame in saying it: Edgartown proper is the preppiest of our towns, arguably the only one in which you might find yourself in the company of gentlemen in jackets and ties. (And no, a slicker and bandana don’t count). Formerly one of the epicenters of the global whaling industry, the center of Edgartown is full of exquisitely maintained captains’ homes, along with some great restaurants with lively bars, lots of shopping, and a harbor full of classic yachts and sport fishing boats.

Edgartown is much more than just the town center, however: the island of Chappaquiddick and the area known as Katama are worlds of their own. There are plenty of fabulous beaches in Edgartown, along with some of the best fishing in the world.

Edgartown Beaches

Norton Point Beach

North Neck Highlands Preserve

East Beach

Edgartown Great Pond Beach

Wasque

Little Beach

Gardner Beach

Chappy Point Beach

Joseph Sylvia State Beach

South Beach

Lighthouse Beach

"I love quiet days, letting the birds wake me up, and going to Edgartown with my wife and boys for coffees and hot chocolates by the docks."

Jesse Hayes

"Dinner in Edgartown at Chesca’s with a pre dinner cocktail on the porch while Mike Benjamin plays music. After dinner cocktail at Alchemy in the upstairs with friends. Perfecto!"

Megan Sokolowski

"Then it’s home to prepare dinner and spend the evening under the stars of the Katama sky with friends. It’s the perfect way to celebrate our good fortune of being on Martha’s Vineyard."

Margo Urbany-Joyce

Primer

A Brief History

Edgartown, Lighthouse, Steve MyrickThe only person ever known to have officially “owned” both the island of Martha’s Vineyard and the island of Nantucket moved to Edgartown in 1646 and sold Nantucket to the first people who made him a reasonable offer for it a decade and half later. Thomas Mayhew had previously built the first bridge over the Charles River, only to have it taken over by the colony before he could recoup his investment through tolls. It appears that he made the decision to sell out of Watertown and purchase the rights to develop the islands partly out of frustration with the Massachusetts Bay Colony. As importantly; particularly to Mayhew’s son, Thomas Jr., who arrived two years before his father, the Island was fertile ground for religious missionary work.

The Mayhews likely were not the first English to take up residence on the Island — various Atherns, Peases, and Nortons had been here already — but the arrival of the Mayhews at Great Harbor marks the beginning of officially sanctioned European settlement. Five generations of Mayhews were missionaries to the Wampanoag, and they had much success with a brand of conversion that was notably more relaxed than some of their contemporaries off-Island. Still, though the missionary efforts were sincere and seemingly benign, the outcome for the Indians of the arrival of the English was heavily weighted toward spiritual as opposed to earthly rewards. The Wampanoag did not, however, disappear entirely from the Island and one of their ancient arts — hunting whales — became the primary industry of Edgartown.

Edgartown, like Nantucket and New Bedford, was one of the great capitals of the international whaling business, which grew steadily throughout the 1700s and peaked in the decades before the Civil War. Though the Vineyard and Nantucket are great sports rivals today, the relationship between the two ports was more of sibling affair, with many of the same families dominating the business in all three ports. The hunt for whales eventually spread to every corner of the globe, whalers from the islands could be found in ports all over the Pacific. The first woman of European descent to spend a night in Japan was Abigail Jernegan, wife of the whaling captain Nathaniel Jernegan. She was also the first Western woman to bring home souvenirs from Japan. There was a kangaroo in Edgartown in the 1850s: Jernegan’s neighbor Caroline Mayhew brought it back from a whaling voyage.

The whaling business collapsed after the Civil War due to a combination of factors, chiefly overfishing of the resource and the discovery of “earth-oil” coming out of the ground in Pennsylvania. The rise of trains on the mainland also marked the end of an era for the Island, as it was now no longer enough to have only a great port. Edgartown declined in population and prosperity along with the rest of Martha’s Vineyard. Its population began to decline in 1860 and didn’t begin to grow again until after the Great Depression of the 1930s.

By then, tourism on the Island was well established, thanks in no small part to the religious revivalists who pitched tents every summer in the Northwest corner of town. The whaling captains of Edgartown invested heavily in developing “Cottage City,” and by 1880 the thing had grown so much that it split off and formed the town that would become Oak Bluffs. But that’s another story.

Oh yeah, that Chappaquiddick thing was in Edgartown. What was that again?

“Settled”: 1642

Incorporated: 1671

Land Area: 27 square miles

Water Area: 95 square miles

Population: 3,779

Getting Around

Chappy FerryEdgartown can be one of the trickier towns to navigate on Martha’s Vineyard. First off, be aware that the island of Chappaquiddick, although it is part of Edgartown, is only accessible by the Chappy Ferry: a little boat that carries about three cars and a handful of people at a time across the 527 foot span of harbor. Round trip tickets are $4 per person, $12 for a car and driver, $6 for a bike and rider, or $8 for a moped/motorcycle and operator. Chappaquiddick is very sandy though, so the best way to see it is via a four wheel drive vehicle, or bicycle. For more information, visit chappyferry.com.

The downtown section of Edgartown has a lot of one way streets, parking is hard to come by, and the roads are narrow, so if you’re biking or driving unfamiliar roads, exercise caution. The good news is many of the shops and restaurants are clustered close together, so once you arrive in Edgartown, you can easily walk from point A to point B.

Where to Stay

Harbor View HotelAn expansive hotel overlooking the harbor and lighthouse, a quaint B&B, an allegedly haunted old mansion…for history, culture, and just plain luxury, Edgartown is a great home base for your Vineyard vacation.

Milk, Cash, Etc.

Your MarketYou won’t have much of a problem finding the essentials in Edgartown. Just know these three areas:

The Triangle

Located at the intersection of Beach Road and Edgartown-Vineyard Haven Road, the Edgartown “triangle” is almost downtown, but not quite. Here, among pizza and sandwich shops and general stores, you’ll find a couple of banks, the Stop & Shop Pharmacy, and just beyond the intersection, the Stop & Shop grocery store. Alcohol and drinks are available at Al’s Package Store and Your Market.

Downtown

You’ll find ATMs at Martha’s Vineyard Savings Bank, Edgartown National Bank, and Santander on Main Street. There’s another ATM off Church Street, at the bus stop and visitor information center. The post office is just beyond here. There are plenty of beach supply shops in the downtown area too, if you forget a hat or sunglasses.

The Airport

Almost in West Tisbury, the Airport business park does not feel like a part of Edgartown, but it is, technically. Aside from the Airport, you’ll find a Mobile station/convenience store/ATM, and couple of restaurants, and a liquor store here.

And don’t forget the Katama General Store if you’re headed towards South Beach!

See & Do

Outdoors

The largest of the down-Island towns, Edgartown has a lot of open spaces to wander outside of its commercial and residential areas. It is home to one of two “great ponds,” large brackish ponds along the South Shore that are great for paddling, wind surfing, and other on the water activities. The bike trails of the State Forest also spill well into Edgartown, along with a number of scenic conservation areas: whether its a stroll along Sengekontacket at Felix Neck or Caroline Tuthill Preserve, or a walk about beautiful Morning Glory Farm.

Arts & Culture

North-Water-GalleryEdgartown arts range from classic to contemporary. Edgartown harbor is home to the Martha’s Vineyard Art Association, an artist/art education group housed in the 240 year old Old Sculpin Gallery, and a handful of other great art shops, jewelers, and funky clothing galleries. You’ll find openings and shows at many of these galleries during the summer, especially during arts strolls, when the parties spill out onto Main Street.

Shopping

Island-Pursuit-ShoppingEdgartown is home to Vineyard Vines, the apparel shop that brought pastels, plaids, and pink shorts to the harbor town. But the shopping options are not limited to preppy styles. You’ll find the funkiest of funky styles at spots like PIKNIK, and along Main Street, art, jewelry, clothing, souvenirs, Jaws memorabilia, you name it. Edgartown center is undoubtedly one of the best shopping centers on the Island.

Eat & Drink

Flatbread PizzaEdgartown is a center of fine dining, chock-full of the kind of places where reservations are a must, drinks are consumed on outdoor patios, and you’d be loathe to wear those beat up old blue jeans inside. You’ll find those kind of restaurants all around Edgartown center. But fear not, if you really had your heart set on wearing those blue jeans, there’s plenty of pizza places, seafood takeout, ice cream and sandwich shops, even a couple of old-timey diners for the bacon and eggs types.