The schooner Alabama and the Island Home ferry share the busy harbor of Vineyard Haven. Photos/New England Boating, Tom Richardson

From schooners to SUPs, boutiques to boatbuilding, Vineyard Haven offers the visiting mariner a mellow mix of maritime history and modern amenities.

Boaters entering Vineyard Haven Harbor for the first time might be forgiven for feeling as if they’d traveled back in time, given the presence of two schooners and the abundance of smaller wooden craft bobbing on their moorings. Ashore, the working marine railway at Gannon & Benjamin only adds to the illusion. But then the Vineyard ferry blasts its horn or a stand-up paddleboarder glides past. The reverie is broken. Vineyard Haven, you see, is modern after all.

Mixing the best of old and new is what this harbor is all about. As the island’s longtime commercial hub, dating back to when it was a schooner stopover known as Holmes Hole, Vineyard Haven has somehow managed to walk the line between cheesy tourism and New England seacoast authenticity. Steel barges laden with heating oil dock alongside 19th-century wooden yachts. Utilitarian grocery and hardware stores share the streets with trendy boutiques and ice cream shops. Restaurants cater to the gourmand and pizza lover alike.

Getting Ashore

Classic wooden boats of all types grace the waters of Vineyard Haven.

While Vineyard Haven may not boast the cachet of Edgartown, the rock-and-roll of Oak Bluffs or the “out-there” atmosphere of Menemsha, it is the most welcoming of Vineyard ports, thanks to its abundance of marinas, most of which offer transient slips and moorings, as well as hourly dockage. You may also be able to tie up for a few hours at the Owen Park town dock, just west of the ferry terminal. Check with the harbormaster.

Yet another option is to drop anchor and dinghy ashore (you can leave dinghies and kayaks at the ferry terminal dock or Owen Park). Anchoring is permitted outside the west breakwater and along the eastern side of the harbor by the oil tanks. Both spots have good depth and holding ground; just be sure to stay outside the main channel.

Anchoring inside Lagoon Pond is also possible; call or hail the bridge tender (VHF 69 for access through the inlet. Mean low water inside the pond channel is eight feet, with at least eight feet inside the pond. However, watch out for the shallow ledge, marked by a “rock” buoy, as you follow the channel south.

Downtown Delights

Kayaks and sailboats are available to rent at Wind’s Up Watersports.

Once your boat is secured, the island is your oyster, and it’s easy to roam thanks to the inexpensive public bus system and numerous car, bike and moped rental agencies in Vineyard Haven. But you don’t need to go far to find sustenance. Within walking distance of the harbor are a host of restaurants ranging from the Net Result, which offers fresh seafood in the rough, to The Black Dog Tavern, which serves hearty fare ranging from breakfast omelets to grilled swordfish, along with a great view of the harbor.

The Black Dog Tavern serves food and drink with a view of the harbor.

A visit to Vineyard Haven usually involves a stop at one of the various enterprises known collectively as The Black Dog. These include The Black Dog Bakery (sells coffee, bread, cakes and pastries), The Black Dog Tavern, and The Black Dog General Store.

If you appreciate classic boats or just want to watch some true craftsmen at work, stop by Gannon & Benjamin, masters in the art of building and restoring fine wooden vessels. The bright, sawdusty shop, brimming with hand tools and redolent with fresh-cut wood, is considered hallowed ground among wooden-boat aficionados.

Farther along Beach Road, just before the Lagoon Pond Bridge, you’ll find Wind’s Up Watersports, where you can rent a kayak, canoe, sailboat, or SUP and explore the protected waters of the harbor or Lagoon Pond. The latter is a wonderfully protected playground for small-boaters.

For an interesting side trip, visit East Chop Light, which dates to the harbor’s glory days as a schooner stopover. The beautiful cast-iron tower, built in 1871, is maintained by the Martha’s Vineyard Historical Society, which also conducts tours. You can easily reach the light, which lies some two miles east of the harbor in the town of Oak Bluffs, by bicycle.

From this superior vantage point you can gaze over the harbor and Nantucket Sound and see why Vineyard Haven was—and still is—an ideal stopping point for boats and boaters of every type.

To check our our Video QuickTour of Vineyard Haven, Part 1, CLICK HERE.

To check our our Video QuickTour of Vineyard Haven, Part 2, CLICK HERE.