Massachusetts' Coastal Community On Martha's Vineyard Boasts Artsy Vibes And Boutique Shopping

For generations, travelers have escaped to Martha's Vineyard for the quintessential summertime getaway. With shingled cottages, bobbing boats in historic harbors, and rolling emerald-green farmland, the iconic island perfectly captures the charm of an English village. Measuring about 87 square miles, the island resembles a roughly triangular shape, ringed by beach and carved out by narrow spits of sand, free-flowing ponds, and rugged bluffs. Near the top of the triangle is the quaint harbor front community of Vineyard Haven, initially named Holmes Hole, according to Vineyard Visitor. It was first settled in the mid-17th century and later became a bustling port for shipbuilding.

Today, petite Vineyard Haven measures less than 1.5 square miles, but is one of the island's main hubs alongside neighboring Oak Bluffs, a resort beach town full of colorful cottages, and the posh, but leisurely Edgartown. Vineyard Haven is especially known for its focus on art and culture, and the Vineyard Haven Harbor Cultural District encompasses the island's theater, history museum, and cinema. Shopping enthusiasts can't miss a stroll down Main Street, dotted with many darling stores, from chic boutiques and a bookshop to homeware centers and the famous Black Dog Tavern and General Store.

Vineyard Haven is accessible by ferry and flights. Direct ferries depart for Vineyard Haven from Woods Hole on Cape Cod, a 45-minute journey that runs year-round, as well as from New Bedford, a 50-minute ride. Vineyard Haven is a 15-minute drive from Martha's Vineyard Airport (MVY), which receives nonstop flights from Boston, New York, Washington, D.C., and Philadelphia, among others. The best time to visit Vineyard Haven is between June and September, when daytime temperatures hover in the 70s, and the season is in full swing. The spring and fall months are chillier, but draw fewer crowds and lower prices.

In Vineyard Haven, art and history are cultivated and celebrated as part of the Vineyard Haven Harbor Cultural District. Learn more about the island's history at the Martha's Vineyard Museum, which has a prominent, picturesque setting that's a short walk or drive from the harbor. Set inside a late 19th-century hospital, the museum organizes exhibits that provide an insightful look at the island's rich and varied past, from its first inhabitants, the Wampanoag tribe, to its later rise as a whaling center, to its popularity today as a well-preserved summertime retreat. 

To experience the artsy vibes of Vineyard Haven, the next stop should be the Martha's Vineyard Playhouse, housed in a former Methodist Meeting House, circa 1833. The playhouse's stage, amphitheater, and art space host a packed calendar of art exhibits, film premieres, plays, concerts, children's events, and other performances between May and October, with more limited programming continuing during the off-season. 

Also part of the Cultural District is the Martha's Vineyard Film Society, where movies are shown year-round, with a number of film festivals held throughout the summer. On the first Friday of the month (between June and October, as well as December), Vineyard Haven buzzes with First Friday art walks when artists come to sell their wares at the alfresco art market, tasty food is served, and live music rings through the historic streets. Art galleries are found throughout Vineyard Haven. At the Louisa Gould Gallery, you can view scenic landscapes and seascapes of the island, as well as island photography. For a unique souvenir, visit Tuck & Holand Metal Sculptors Studio on State Road, where artist Anthony Holand crafts custom weathervanes, island wall maps, and large-scale metal sculptures.

Vineyard Haven's Main Street is lined with some of the island's best shopping. Peruse The Beach House for chic homewares that will infuse your home with the island's coastal charm. A local institution is the Bunch of Grapes bookshop, a locally owned business that first opened in the 1960s with both bestsellers and lesser-known tomes by local authors. Children will adore the Tisbury Toy Box, well stocked with games, puzzles, and more, while both aspiring and expert musicians can't miss the instruments on display at Island Music. Vineyard Haven channels New York concept-store cool at Lennox & Harvey, and fashionistas can browse stylish silhouettes made from high-quality materials at Seven Sisters.

However, any visitor to Vineyard Haven must stop by the Black Dog General Store, as the ebony-colored Labrador Retriever is now the iconic logo of the island. The Black Dog Tavern, overlooking the harbor, is a cozy spot to savor classic New England fare, like clam chowder and lobster rolls. Afterwards, browse the Black Dog merchandise at the next-door general store.

For a taste of Vineyard nostalgia, dine at ArtCliff Diner, a retro diner that's been in business since 1942. A short walk towards the water will bring you to the buzzy Beach Road restaurant, which features local seafood creatively prepared with globally-inspired flavors. Waterside Market on Main Street is the best spot for delicious provisions — such as hearty sandwiches, fresh coffee, or baked goods — to pack for a beach day. We recommend driving 5 miles west of Vineyard Haven to the Caribbean-like waters and white sand of coveted Lambert's Cove Beach.