“VH,” as we say, is the official year-round town of the Island. There are plenty of people who live in the other towns off-season, but because this is where the ferry service runs twelve months of the year, Vineyard Haven is the economic center of the Island. It’s a handsome, unpretentious town with a working waterfront, a couple of decent restaurants and hotels, good shopping, legendary boat building, and a few exclusive neighborhoods where you may or may not be able to find a rental. It’s the most beach-deprived town on the Island, however, so if sun and sand are all you crave it may not be the place for you. Also, while the town recently approved liquor sales at restaurants, there are no bars or liquor stores.

Vineyard Haven Beaches

Tashmoo Beach

Tisbury Great Pond Beach

Owen Park Beach

"We wander down to town – pick up take out from the Art Cliff truck or the Net Result, head to Owen Park for another glorious picnic and sunset on the beach."

Nevette Previd

"Spend the afternoon poking around the shops of Vineyard Haven’s main street, especially Nochi, the Beach House, and Bunch of Grapes for a great summer read."

Megan Sokolowski

"We collect them in a bucket, then gather up all the other kids on the pier and have crab races back to the water."

Sally Taylor

Primer

A Brief History

Schooners, Alabama, Shenandoah, Sailing, Vineyard Haven Harbor, Alison ShawLet’s see if we can make this confusing: Tisbury is the official name of Vineyard Haven, and Vineyard Haven is the main year-round town on the Island, but Vineyard Haven was not originally the town center of Tisbury, which was actually what is now called West Tisbury. And it wasn’t called Tisbury or West Tisbury, but Middletown, while Vineyard Haven was really called Holmes Hole, which was a corruption of Homes’ Hole…and on and on, back to the Wampanoag name Nobnocket and beyond.

All that being said, there’s little doubt that the sheltered waters of Vineyard Haven Harbor were visited by sailing vessels for decades before the 1660s and 70s, when various English families began to build houses around the harbor and the lagoon. By the end of the 1700s, the route up and down the coast through Vineyard and Nantucket Sounds made those bodies of water second only to the English Channel in terms of shipping traffic, and Vineyard Haven had grown into a bustling port town with about 350 residents. There were salt-works, ship’s chandleries, ropewalks, sail lofts, blacksmith shops, a harness factory, and an assortment of inns and taverns. There were whaling captains in Vineyard Haven, as in Edgartown, but the main orientation of the harbor throughout the Age of Sail was toward the coastal trade that passed through the Vineyard Sound.

As the village grew, some of the residents began to chaff at having to tell off-Islanders they lived in a hole and agitated for calling the place Tisbury Harbor, but in 1871 the voters opted for the more scenic name of Vineyard Haven. Unfortunately, most of the scenic part of town burned to the ground in the Great Fire of 1883, which started in a harness shop and in six hours destroyed thirty-two homes, twenty-six stores, twelve barns, two stables and a church. All the other towns of the Island came to the aid of Tisbury, and the waterfront was rebuilt with remarkable speed.  But by that time the interests of the maritime residents of the harbor area had diverged from those of the more agricultural population Tisbury, to the point that the rural residents up Island, in particular, wanted a divorce.  When the split came in 1892, the community around the harbor kept the original name and the up Island town became West Tisbury.

Vineyard Haven is still the hardest working harbor on the Island, the port of entry for virtually everything imported from off-Island. It’s also a famous center of wooden boat building and maintenance, with the tall ships of the Black Dog empire usually at anchor in the harbor and the legendary boat yard of Gannon and Benjamin turning out the worlds most beautiful handmade sailing yachts.

The summer scene is historically the most eclectic on the Island, ranging from the surprisingly stuffy “tennis whites only” crowd at West Chop, to the incoming hoards of day-trippers, to the old guard literary lions of Main Street, to the regular year-rounders who, believe it or not, also love summer on the Vineyard.

“Settled”: 1660

Incorporated: 1671

Land Area: 6.6 sq mi (17.0 km2)

Water Area: 12.6 sq mi (32.6 km2)

Population: 3,805

Getting Around

Vineyard Haven is the year-round entrance to Martha’s Vineyard, and for this reason, the transportation situation is relatively easy. Immediately after arriving in Vineyard Haven, folks departing the ferry can find the VTA bus terminal (with routes all over the Island), a taxi stand, car/moped rentals, and a couple of bike places.

We’d say getting around VH is a cinch, but do beware the dreaded Five Corners. This five way intersection, just past the boat terminal, only has two stop signs and a lot of heavy traffic. Go slowly, mind your traffic rules and your manners, and if you’re lucky, a friendly driver or police officer might be there to wave you through.

Where to Stay

Hotels in Vineyard Haven are defined by their history. The Mansion House Inn on Main Street, established in 1791, caught fire in the early 2000’s; the blaze was fought by volunteer firefighters who rushed from a formal event still in their tuxedos. It has since been restored. The 1720 house, a bed and breakfast, has been there since — you guessed it — 1720. Vineyard Haven doesn’t have the most lodging on the Island, but it’s few hospitable havens are all worth the stay.

Milk, Cash, Etc.

Stop & ShopVineyard Haven not only has all the supplies you could possibly need, but it has them year-round (a Vineyard miracle). VH has not one, but two grocery stores: Stop & Shop, near the ferry terminal, and down-Island Cronigs, off State Road. Vineyard Grocer, also off State Road, offers essential groceries plus some interesting specialty foods.

There are two gas stations off Beach Road, one with a convenience store. A hardware store is nearby, as well as a Cumberland Farms. Next to that is the post office.

Need something else? Just take a stroll along Main Street (for ATMs, beach supplies etc.), or a drive up State Road (for car parts and more), and you’ll likely find it.

See & Do

Outdoors

Sail BoatsOutdoor opportunities in Vineyard Haven are aplenty, you just need to know where to look. For instance, look over the Tashmoo overlook on State Road, for an exceptional view of moored sailboats framed by fields. How about mini golf, or a try at the Island Adventure rock wall? A nighttime ghost tour? Rent a paddleboard at Winds Up and tour Lagoon Pond. Or, enjoy a sunset drink aboard one of the Black Dog Tall Ships.

Arts & Culture

Seaworthy GalleryThe arts scene in Vineyard Haven has always been strong, but lately it’s been making a comeback. In fact, the town was recently designated a “cultural district” by the Massachusetts Cultural Council. There are enough art galleries on Main Street to appease art lovers of all tastes. Not to mention two movie theaters, a performing arts venue, some dance studios…Vineyard Haven even has it’s own town band.

Shopping

Rainy DayYou won’t find many of the average tourist trinket shops in Vineyard Haven. In fact, you’re more likely to find a sofa that you can neither live with out nor take back on the boat. The shopping opportunities are varied: everything from high end furniture and clothing boutiques, to kitchen and home goods stores that will inspire you to be America’s next Top Chef. You can even buy a surfboard here, but the real heart of the Vineyard Haven shopping scene is the art (see Arts and Culture).

Eat & Drink

La CaveWhether you’re in the mood for Asian fusion, Brazilian, Mexican, pizza, or quite possibly the biggest and best sandwich you’ve ever eaten, there is a spot in VH. Plenty of take out, plenty of sit down, and all things in between. Vineyard Haven is also a great snack spot for coffee, baked goods, ice cream, froyo, and smoothies.

Good to know: Vineyard Haven is a partially dry town, so the few establishments that can serve alcohol can only serve wine, beer, and saki. It’s a good idea to call ahead for this information.