Vineyard Haven lights up at night. Photo provided by Martha's Vineyard Chamber of Commerce/ David Welch Photography

Lake Tashmoo remains one of my favorite ways to visit Martha’s Vineyard. This quiet salt pond, accessible through a narrow cut from Vineyard Sound just west of West Chop, has a bucolic, almost inland feel, especially at its headwaters. It also offers a unique way to access downtown Vineyard Haven without having to go through the busy main harbor.

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Vineyard Haven Chart

You can bring your dinghy or kayak to the 25-acre Tashmoo Springs Park at the southern end of the pond, the site of the old Tisbury Water Works (and the source of fresh water pouring into the lake). There, you can throw out an anchor or tie off to a tree

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at the water’s edge and head east for a half-hour walk through some residential streets and down a slope into the vibrant center of Vineyard Haven.

This busy harbor town is the island’s commercial capital. Vineyard Haven remains a place where year-round residents go about their daily work, calmly letting waves of seasonal visitors from the ferry landing and marinas wash over their community.

Lake Tashmoo Chart

In the 19th century, Vineyard Haven (then called Holmes Hole) thrived as one of New England’s busiest harbors. The main shipping lane from New York to Boston and Europe passed through Vineyard Sound, and that stretch of water carried a volume of maritime traffic second only to the English Channel. When the wind blew foul or the sound’s strong tides ran in the wrong direction, sailing ships—sometimes as many as 300 at a time—dropped anchor in the harbor nestled between the points of East and West Chop. These short-term visitors made use of the industrious chandlers and shipwrights of Holmes Hole to stock up on last-minute supplies and make final repairs before heading into the Atlantic. Shipyards lined the harbor’s southern shore, building and repairing wooden craft of all sizes, and many a Vineyard lad started a life at sea by signing on with a visiting schooner or square-rigger.

…visitors are welcome on the grounds of
East Chop Light, a beautifully symmetrical cast-iron tower built
in 1871…

East Chop Light sits on Telegraph Hill, so named for the semaphore station once used to communicate with ships and the mainland. Photo provided by Martha's Vineyard Chamber of Commerce/Mark Lovewell

When steam and steel took over from wood and canvas, the shipping lanes shifted away from Martha’s Vineyard. In 1871, as tourism started building into an economic mainstay for the island, Holmes Hole adopted the more genteel-sounding name of Vineyard Haven. The town remained the center of island commerce—the place where Vineyarders unloaded supplies and visitors came ashore via the ferries of the Woods Hole, Martha’s Vineyard and Nantucket Steamship Authority. However, the harbor slipped briefly into a quiet decline as a port of call. Recreational boats gravitated to Edgartown—the elegant former whaling port at the eastern end of the island.

The Black Dog Tavern is now known worldwide. Photo provided by Martha's Vineyard Chamber of Commerce/ Betsy Corsiglia

Upon entering Vineyard Haven, the first things you’re likely to notice after rounding East or West Chop are the towering masts of the topsail schooner Shenandoah or her sister ship Alabama, a sight that harks back to the glory days of Holmes Hole. Even if both windjammers are out on charters, you’ll probably spy a forest of other masts—many of them wooden—poking up from behind the breakwater protecting the inner harbor. Sailboats of all sizes, and countless powerboats, will be moving in and out. It’s good to reserve a spot in advance, but even on crowded summer weekends the harbormaster can usually squeeze you in somewhere.

Along the waterfront, at the north end of the harbor center, the Steamship Authority ferry pier regularly disgorges cars and passengers. Whenever a car-carrying ferry docks, offloading vehicles briefly clog Vineyard Haven’s narrow streets. The town was meant for walking or biking, and you can rent bikes at Martha’s Bike Rentals—one of Vineyard Haven’s many rental shops—south of the Steamship Authority dock, at the busy intersection referred to by locals as “Five Corners.”

Ferries shuttle passengers from Woods Hole to Vineyard Haven and back again multiple times each day. Photo provided by Martha's Vineyard Chamber of Commerce/ Max Bossman

The short walk along Water Street takes you past the various enterprises known collectively as the Black Dog. Founded by Robert Douglas Sr., the owner of the Shenandoah and Alabama, and operated along with his 3 sons, this expanding set of businesses (officially known as the Coastwise Packet Co.) includes the Black Dog Bakery—where we stop for coffee, fresh pastries and some rolls to pack for our biking adventures—the Black Dog Tavern, and the Black Dog General Store, purveyor of hats, coffee mugs, sweatshirts and T-shirts, all bearing the signature image of the Labrador-mix that was Douglas’s faithful sailing companion for 16 years.

Douglas started the Black Dog Tavern—a restaurant at the foot of his very own Black Dog Wharf—in 1971, as a place where sailors could enjoy a hot meal at any time of year. Its reputation quickly grew, and the tavern now serves breakfast, lunch and dinner to boaters, day-trippers, summer folk and islanders alike. Oh, and it also serves alcoholic beverages now that the ban on such libations has been lifted.

West Chop Light is a private residence. Photo provided by Martha's Vineyard Chamber of Commerce/ Betsy Corsiglia

But on to more nautical matters: Vineyard Haven’s deep harbor lies between 2 steep, protective headlands, known as East and West Chops—names that aptly describe the state of the water off each point when the tide in Vineyard Sound runs against the wind (“chop” also happens to be an old-fashioned term for the headland of a harbor). Lighthouses, dating from the harbor’s glory days, stand on each chop; West Chop Light is closed to the public, but visitors are welcome on the grounds of East Chop Light, a beautifully symmetrical cast-iron tower built in 1871 and maintained today by the Martha’s Vineyard Historical Society. You can easily reach this light, which lies just over the town line in the neighboring town of Oak Bluffs, by bicycle. The tower, with a commanding view of Vineyard and Nantucket Sounds, stands on Telegraph Hill, named for a semaphore station that once stood there to relay messages to and from Cape Cod and Nantucket and to signal the passage of ships through the sounds.

Children can play at the beach alongside the ferry terminal. Photo by Tom Richardson

If you like to shop, a visit to Main Street—Vineyard Haven’s principal shopping street—is in order. Wide enough for only one lane of cars and clogged with pedestrians on weekends, Main Street embodies the contradictions of Vineyard Haven. T-shirt shops, soft-serve ice cream and exclusive clothing and kitchen-ware boutiques stand side-by-side with Brickman’s, a generations-old clothing store. Midnight Farm, down the hill on Water Street near the ferry landing, carries top-drawer gifts, home furnishings and children’s clothing—and it’s co-owned by entertainer Carly Simon, a year-round resident of the Vineyard.

Vineyard Haven Harbor is chockfull of gorgeous boats. Photo provided by Martha's Vineyard Chamber of Commerce/Nicole Friedler Photography

A view of Vineyard Haven from just outside the breakwater. Photo provided by Martha's Vineyard Chamber of Commerce/ Max Bossman