A Brief History of Vineyard Haven Harbor

Excerpted with permission from Schooner: Building a Wooden Boat on Martha's Vineyard, by Tom Dunlop.

Until the opening of the Cape Cod Canal in 1914 - and depending on the direction from which the schooners, tugs, and barges sailed - Vineyard Haven was either the first or last harbor they could tuck themselves into on the perilous coastal highway between New York and Boston.

For two hundred years, the traffic between these two towns had been heavy and it picked up sharply during the Industrial Revolution: In 1883, for example, the Cross Rip Lightship, anchored ten miles east of Vineyard Haven as a sentinel in the very heart of Nantucket Sound, counted some twenty thousand passing vessels. Many ships dropped anchor in Vineyard Haven when the tides or weather went against them, or supplies ran low, or something broke on the voyage.

Vineyard Haven grew up on all this transient commerce. In the village of those days, there were lofts to mend sails; a shipbuilding company to repair hulls and rigging; a marine hospital; and a Seaman’s Bethel to minister to sailors, body and soul - and sometimes spirit. Between 1865 and 1915, some two thousand ships were wrecked, and more than seven hundred lives lost, between Gay Head at the gateway to Vineyard Sound and Provincetown on the tip of the Cape. In Vineyard Haven there are two cemeteries where dozens of shipwreck victims, sometimes known but often not, were buried.

Vineyard Haven, called Holmes Hole until 1871, was also a town of shipbuilders. Beginning in the middle 1840s, the Holmes Hole Marine Railway - known today as the Martha’s Vineyard Shipyard - built at least a dozen large schooners and brigs on a sandy isthmus dividing the harbor from an inland lagoon. Between the autumns of 1942 and 1943, thousands of feet of harbor shoreline were commandeered as an open-air construction site where shipwrights and house carpenters worked furiously to build barges and scores of high-speed rearmament and personnel boats for World War ll. And for nearly forty years, between 1931 and 1969, a craftsman named Erford Burt, whose formal education ended after one week of high school, built many of the Vineyard Haven racing sloops that Nat Benjamin was restoring in his workshop in the late 1970s.

But what drew together the working past and wooden-boat building future of Vineyard Haven Harbor was the arrival of a topsail schooner named Shenandoah in July 1964. She was 108 feet on deck, carried 7,000 square feet of cotton canvas, and her two sharply raked masts towered over everything else on the water. Designed by her owner and master, Robert S. Douglas, who in a few years would build The Black Dog Tavern on the Vineyard Haven waterfront, Shenandoah was intended to take thirty passengers on weeklong cruises up and down the southern New England coastline.

A generation had passed since a commercial sailing vessel had called Vineyard Haven her homeport. Shenandoah was modeled on Joe Lane, a square-rigged revenue cutter that chased down pirates and tax cheats along the eastern seaboard in the middle of the nineteenth century.  Like Joe Lane, Shenandoah had no engine. Kerosene lamps lit her saloon and navigation lights. Her stove was fired by coal, her dining room table was gimbaled to counteract the motion of the sea, and she carried a chanteyman who sang on deck when the schooner rode at anchor as the sun went down. Her passengers could experience nothing more authentic by way of old-world sailing ships in the twentieth century than a cruise on Shenandoah.

There were always among her crew each summer one or two traditionally minded young men who decided a harbor that supported a schooner like Shenandoah was a harbor they couldn’t quite bear to leave. So they stayed, bought old wooden boats of their own - the only kind they would ever countenance, and the only kind most could then afford - and began to form an offshore neighborhood on Vineyard Haven Harbor. “In those days,” says Gretchen Snyder, who would soon join Gannon and Benjamin as a sail maker, “there were about six of us living on boats, and you’d call over and say ‘What’s for dinner? It was a small community, and everyone did all their own work on their boats. It was very community-oriented, working together to get what we needed."