Jeffry Thompson, a dairy farmer from Michigan, became first mate of the topsail schooner Shenandoah in the summer of 1991, when he was twenty-nine years old. But his journey  from farm boy to seaman – and, eventually, back again – began years before, when he was fifteen and left his family’s Midwest farm to join his brother Timothy, who was sailing charters around Washington’s San Juan Islands. Jeffry had never sailed a day in his life – had never been in anything bigger than a canoe – but was soon earning his keep swabbing decks and cleaning heads on his brother’s boat. He fell in love with the whole world of sailing. “The first day I could not see any land,” he says. “That’s overwhelming, when you’re out there and all you can see is water and waves and waves and waves.”
 
Eventually the Thompson brothers jumped over to Star Pilot, a 124-foot pilot boat out of Boston, and sailed to Oregon, Hawaii, down the coast of California as far as Mexico, then back up to Santa Barbara. Though this was southern California, Thompson began to hear regularly of Bob Douglas and a square-rigged, two-masted schooner called Shenandoah, which was carrying passengers on weeklong trips up and down a small stretch of the southeastern New England coastline, three thousand miles away on the diagonal.

Shenandoah, 108 feet at the rail, was modeled after the Joe Lane, a swift, lightly armed revenue cutter that hunted down tax cheats sailing the eastern seaboard in the middle of the nineteenth century. When Shenandoah sailed into Vineyard Haven harbor for the first time, forty years ago this month, most of the other schooners in the charter trade were weary old freight vessels and fishing boats converted, with varying degrees of care, to carry passengers. Some of them, one writer said in 1964, were “actually falling apart.” Shenandoah, only the second schooner ever built new for the charter business in the twentieth century, was something altogether different – a realization of ideas that drew from disparate sources and centuries, contradictions so confounding that for a year after her launch the Coast Guard refused to grant the vessel a license to carry paying passengers.

Shenandoah was a modern passenger boat based on the plans of an archaic patrol boat, a twentieth-century cruising vessel rigged like a nineteenth-century clipper ship, a sailboat whose raked masts, sharp bow, and rounded, concave stern made her look faster standing still than most sailing vessels do underway. Her skipper did strange and wonderful things with her – braced up her square topsails, which were designed to catch the breeze like a parachute and drive a vessel downwind, so that they actually helped her go the opposite way, into the wind itself. An observer – cataloguing these conflicting intentions, elements, and accomplishments in her design – might easily overlook two genuinely stupendous things about her: Shenandoah was only the second commercial sailing ship built without an engine in the United States since 1921. And Douglas, her owner and master, had modified her lines and rigging from the Joe Lane himself, without ever having spent a day in a school of boat design.

“Bob is well known to everybody from coast to coast. Everybody knows who Bob Douglas is,” says Thompson, who with his wife Elizabeth now runs Thompson Farm and SBS, the lawn, garden, and feed store, both in Tisbury. “Other than Havilah Hawkins in Maine, who Bob worked for originally, Bob has been the leader of this whole schooner revolution in the entire country, coast to coast.” Back in his Star Pilot days, having heard about Bob Douglas, Thompson had sailed through the Panama Canal to the East Coast and, after turns on a few other boats here and there, wound up in Vineyard Haven, looking for a berth on Shenandoah. “I chased him. For a long time,” says Thompson, smiling. He wasn’t sure Douglas would want a dairy farmer as first mate, the man charged with the operation of the schooner from fitting out in spring to decommissioning in the fall, no matter how much sea time that dairy farmer might have. “I chased him for almost a year before he finally said okay.”

In the spring of 1991, Thompson became one of eighteen men who know what it means to be, in effect, the chief executive officer of the longest-serving schooner under one command in the American coastal-cruising business. Nobody has done this work longer than Robert S. Douglas. And nobody knows this ship and the way Douglas has sailed her for forty years better than the men who have served as his mates. Eleven of the eighteen still live on the Island, and each had good reason to stay when their hitches were done, says Thompson: “If Bob trusts you to be his mate on the schooner, you automatically have the trust of half the people on the Island – at least the people that were here ten or fifteen years ago, the people that knew Bob. If you can get on as Bob’s mate, you’ve got it made. You really do. I think the reason a lot of us have stayed is the reputation that you get just for working for Bob on the boat.”

Gary Maynard came aboard Shenandoah in 1979 as galley boy, having completed a round-the-world voyage with his family the year before in a home-built replica of Spray, the sloop in which Joshua Slocum became the first man to sail alone around the world in 1898. Maynard, who served as mate in 1986 and now runs Holmes Hole Builders in Vineyard Haven, recalls a fundamental legacy of Shenandoah and her master – the setting and keeping of a certain set of standards, passed down from mate to mate, and thus crew to crew.

“We had to serve forty people five-and-a-half days a week from Monday morning through Saturday lunch,” Maynard says. “The galley’s about six feet square, seven feet square.” The stove on Shenandoah is coal-fed, and except when the watch tended it, Maynard had to keep it fired morning, noon, and night. He was sixteen at the time. “I had to set the tables and clear the tables and serve the meals and wash the dishes by hand and do all the prep-cooking and clean the galley, five-and-a-half days a week. Everybody took their responsibilities so seriously on the boat that I did too. I was a pretty serious kid, anyway. The tables are really long, and I’d get down at the end of the table, and I’d line up the glasses and I’d line up the silverware so that everything was set perfectly. I had all these systems for doing the dishes.” Billy Mabie of West Tisbury – who has a license to serve as master on any steam, motor, or sailing vessel of any gross tonnage on any ocean, and who now works as chief mate on ExxonMobil tankers – was serving as mate for the third consecutive summer that year. “Billy used to come in sometimes and run his finger around the lip of the skylight and see if it was clean. I knew that he was half-kidding, but on the other hand he was serious, and this was how the boat was run. I mean, we had a basic philosophy: there were no mops and no brooms on the boat; there was only foxtails and sponges, because you had to be close to the dirt. And it wasn’t a joke. It was an amazing group of people to be around, a group that was totally dedicated to this boat.”

Captain Douglas was then a more remote figure on deck than he is reported to be these days, now that he is older – seventy-two – and has shifted from taking adults on weeklong charters to taking children. Often these are Island fifth graders, chaperoned, whose imaginations are more receptive and whose lives are more joyfully influenced by the experience than adults allow themselves to be. The standards came down from the captain, Maynard says, but enforcement fell to the mates who, in the 1960s and 1970s, could be tough. Once, after rounding-to and anchoring in Nantucket, Mabie gathered the crew on the foredeck and read them the riot act because one of the buntlines – a line that helps to furl a topsail – hadn’t been hauled home. “Bob had noticed it and mentioned it to Billy,” Maynard says, and the lapse had touched the first mate deeply. “It just wasn’t perfect,” says Maynard who, as mate, could also feel it when standards weren’t met. One day a deckhand failed to thoroughly trim and clean the oil lamps in the main saloon. “And Bob during dinner took all the lamps up on deck and was trimming them, just muttering to himself. And I was so mad I threw the guy overboard in his clothes.”

This may be an odd moment to bring up “the camaraderie of the crew,” but the subject has been central to the theory of the ship from her first days at sea. “There is certainly some vicarious satisfaction in providing a training ship for my crew of eight,” the captain wrote in Sea History magazine in 1986. “There was no such vessel operating in Massachusetts when I was sixteen years old. One of my greatest satisfactions lies in seeing young men come aboard in the most humble crew positions and climb through the ranks, the vessel training the crew; and seeing them perform as mate, my most  important position; and seeing them go on and wring more water out of their socks than I have sailed on.… The obligation and responsibilities of the crew to one another and to the vessel produce a lifestyle that one has to experience to understand. Slocum and Villiers both speak eloquently of the magic done aboard a real sailing vessel to those involved with its welfare and operation. Those who have experienced it know it is there.”

Maynard looks back and agrees. “I remember feeling passionate about how important it was to carry this torch. Now I see that it’s not as important. But at one time I thought it was the most important thing I could do. I think that your own legacy – if you’re a family man, your real legacy is your kids, and that’s what’s important: to leave the world with good people if you can. I think what was important about Shenandoah was that reaching for excellence, that desire to just do it right. And in a way it poisoned me a little bit for working on other boats, because I was always this difficult, demanding person on these other crews that were more relaxed. And so I didn’t always do well in that environment, because I wanted it to be right. I just wanted it to be good. On Shenandoah, you’ve got to do it right. You’ve just got to do it right.”

The story of Shenandoah begins with a peapod – a double-ended tender that Bob Douglas saw nodding behind a Friendship sloop as it sailed into Vineyard Haven back around 1952. Douglas was twenty years old, a West Chop summer resident of five years’ standing, but this sharp, old-time little dory – “all painted up like the proverbial little red wagon: dark green hull, black waist, white guards” – caught his eye. He jumped into a plywood skiff and rowed over to the sloop. “Where did you get that boat?” he asked. The answer came back, “Just write Havilah Hawkins, Sedgwick, Maine.” From Hawkins, Douglas commissioned not only a peapod of his own but also, in a way, the rest of his life at sea. In the summer of 1960 Buds Hawkins would hire Douglas as mate aboard the schooners Stephen Taber and Alice S. Wentworth and prove to him that a substantial sailing vessel could support herself carrying passengers on weeklong cruises out of established ports. In the winter of 1961, Hawkins also showed that you could do it with a boat built new. From the Harvey Gamage yard in South Bristol, Maine, Hawkins commissioned Mary Day, an eighty-eight foot, shoal-draft windjammer, widely believed to be the first American sailing vessel built to carry passengers in the twentieth century. Douglas ran errands for Hawkins, planed a few planks for Mary Day, and watched the Gamage yard at work for the year it took to build her. He decided Gamage was the yard to build the schooner he had dreamed of for himself. “Before Mary Day was launched,” says Douglas, “I had to give Harvey a thousand-dollar check to keep my place in his production line.” He signed the
contract and drove around with the check tucked in the visor of his car for a week. “At least a week,” says Douglas. “It was a big step, literally conditioning everything I did after that.”

The first time Douglas caught sight of the Joe Lane, the revenue cutter on which Shenandoah was based, was while he was thumbing through a copy of The History of American Sailing Ships, by Howard I. Chapelle, in Buds Hawkins’s living room. He cut down the sail area of the Lane to seven thousand square feet, so that a mate, bosun, and three deckhands could handle the spread of canvas along the lower fore-and-aft-rigged sails, and the square sails aloft. He raised the freeboard, or sides, from eighteen inches to three feet. And he filled out the stern so that it would ride a following sea better and make the shape of the hull more symmetrical.

“I remember visiting him in the house down here before Shenandoah was actually in the works, when he was drawing her, and he was wildly enthusiastic,” says Tony Higgins, a builder and carpenter from Christiantown, who would  become Shenandoah’s first first mate in 1964 and 1965. Douglas has always played down what it took for a self-taught boat designer to reconceive a nineteenth-century armed ship as a twentieth-century passenger boat, but several mates note that a significant error anywhere could have left him with a $169,000 topsail mistake – or a vessel that, at the very least, would take many seasons and many thousands of dollars more to put right. “A lot of it was trial and error,” Higgins says of the process Douglas went through. “This wasn’t anything that someone had just gone and done. This is why he’s an impressive guy, because he did this.”

Shenandoah went flying down the Gamage rails into the Damariscotta River on February 15, 1964, Higgins hoisting a staff and American flag the moment she cleared her shed. She made Vineyard Haven safely on the afternoon of July 15, 1964 – and then things got challenging. The Coast Guard refused to grant her a license to carry passengers. On August 12, 1955, the Levin J. Marvel, a 128-foot schooner carrying twenty-three passengers and a crew of four, had turned broadside to a northeast gale, capsized, and sank in Chesapeake Bay, killing fourteen people. “Historically,” says Douglas, “the Coast Guard’s involvement with licensing sailing passenger vessels was this: any sailing vessel up to 700 tons didn’t have any inspection or licensing. Zero.” Mary Day, the Hawkins schooner, had gone into business without a stability assessment in 1962, but with Shenandoah the Coast Guard balked, insisting Douglas prove that she could be knocked over onto her beam-ends – nearly 90 degrees – and right herself again. No vessel of Shenandoah’s design and size could ever do such a thing, and a skilled captain would guard against the risk by shortening sail before she ever faced the danger. The real problem, wrote Joseph Chase Allen of the Vineyard Gazette, “appears to be that the executives, at least, of the U.S. Coast Guard no longer know sail, and there are no regulations covering a sailing vessel designed for carrying passengers.”

For a season, Douglas carried passengers for free. At last the vessel found a Coast Guard executive who knew sail – W. J. Lewis Parker, the officer in charge of marine inspections in Boston, who had sailed schooners as a kid. Parker signed a stability certificate and on June 25, 1965, Shenandoah was allowed to set sail with paying passengers for the first time ­– but not before a Coast Guardsman, making a final inspection, insisted that a frame be purchased for her hard-won but unframed
license. “It entailed a mad dash up to Main Street,” said the Gazette, “before the Shenandoah could spread her wings and head for the unpetty world of the open sea.”

Around vineyard haven harbor, there’s a rumor that Bob Douglas, after forty seasons on the
water, has never actually seen his vessel sail, so wedded is he to the helm of the boat. “He’s actually kind of a wheel hog,” says Billy Mabie, the first mate from 1977 to 1980. “To say the least!” says Tony Higgins, the first first mate. “The first or second year, supposedly, he hopped off onto a speedboat with somebody he knew and drove off for a few minutes [to look at her under sail] and then came back,” says Bill Austin, a land surveyor from West Tisbury who sailed as mate in 1981. Gary Maynard, the mate from 1986, was once given the chance to command Shenandoah alone over to Fairhaven for spring haulout – but this was under tow, behind a tug. “It was the first time he’d ever not steered the boat out of the harbor,” says Maynard, who had just skippered Star Pilot – Jeffry Thompson’s old schooner – up the coast from Mexico. “So he said to me, ‘I suppose if you can get up from Mexico, you can follow a towline over to Fairhaven,’ and that was all he said. But that was as big of a compliment as you can get.”

What the Vineyard mates all say about Douglas is that he has an unrivaled set of shiphandling skills that made sailing with him a matter of pride and a hell of a lot of fun. The matter of ability comes up early in any conversation with them, and always before they are asked. “Boy, what he could do,” says Matthew Stackpole, executive director of the Martha’s Vineyard Historical Society, who served as mate from the second half of 1967 through 1969. “We used to go to the America’s Cup races at the end of the year, and it was when Dame Pattie, the Australian, was competing with Intrepid. And Newport harbor was alive with vessels, of course, and we would sail in and out, and without an engine – you know, you don’t have an engine; you have to sail. So we came back one time and a lot of other vessels had gotten in before we had, so there wasn’t much room left in the harbor. We had everything up, sailing along, probably doing seven or eight knots, easily. And with all that sail up, seven thousand square feet of sail – there was an enormous amount of power.

“We came screaming in between Fort Adams and Goat Island into Newport harbor, and Bob sails in amongst big vessels and little vessels, and came into the middle of the only place in the entire harbor where there was enough room for us to round-to and stop. We used to stop her with the topsails. We’d head into the wind and back the topsails, which then become a big brake. They stop you cold – and then, of course, they start pushing you back. Bob would use them to set the anchor. So, anyway, we came screaming in, got the anchor over, stopped her, got the sails off, and as we were standing on deck, getting ready to get the foresail and the mainsail down, they towed Dame Pattie by us, and the whole crew of Dame Pattie stood on the rail and applauded. It was great.”

The mates also agree that the man himself has changed. In 1970 he married Charlene LaPointe, then a mariner scout leader, who now runs Arrowhead Farm, the family home in West Tisbury, where she gives riding lessons and boards horses. They have four sons: Rob, Jamie, Morgan, and Brooke. Jamie and Morgan both sailed as mate for their father, and Jamie is now serving his second stint as master of Alabama, a 1926 pilot boat from Mobile, Alabama, converted to the charter business, whose rigging Douglas designed and whose restoration was completed by Gary Maynard in 1997. Maynard says the days when mates threw sloppy deckhands overboard are long gone. “Bob was a different man,” Maynard says of the period when he was aboard. “He had these flaming red muttonchops, and he was very remote. We hardly spoke to him. We always called him ‘Captain Douglas.’ And he would stay back in the stern by the wheel and look at the rigging with his binoculars and say, ‘Okay, well, the fourteenth batten needs a new seizing; it’s down an inch.’ You’d have to go up there and fix it. It’s different now. He’s a completely different man. Much more relaxed. And the boat is different for that reason.”

The boat is also different because of a change in philosophy and in clients that began almost fifteen years ago. Jeffry Thompson’s first year as mate was also the first in which Shenandoah began to shift away from carrying adults as passengers.

“And it seemed like every time we went anywhere,” says Thompson, “we’d leave the harbor: ‘Where’s the bar?’ They wanted to go to a town with a bar. And Bob and I talked a lot about it. What a pain these people were! We’re out on this big, beautiful ship, and a beautiful harbor, with islands and sounds, great sailing – and they wanted to go to Newport and go to the bar. We took the first load of kids that year. It was one of the first loads of local kids that Bob had taken, other than sea scouts. They were great. They had all kinds of questions. They jumped in the rigging. They wanted to learn everything. We set up classes and taught ’em a lot of stuff, what all the lines and rigging were. All they wanted were hot dogs. They wanted hot dogs and the beach. And the second year we carried all kids. And he’s carried kids ever since.”

Douglas wants to reach these children – particularly Vineyard children – before adolescence, before they finish walling up their ability to be startled and amazed. Shenandoah and Alabama carry some six hundred kids a summer on schedules that run from a day to a week. He hopes that his young passengers will go ashore newly impressed by ideas that the modern world teaches less emphatically than perhaps it should: That the way you do things matters. That mastering something big and complicated can be fun. That great goals can be achieved if everyone learns together and pulls together.

And that what Vineyard Haven harbor is matters a great deal to the heritage and character of the Vineyard.

A few years ago, Ginny Jones – who was then the office manager of the Gannon and Benjamin Marine Railway, which builds and repairs wooden boats one wharf down from Douglas’s office at The Black Dog Tall Ships Company on the Vineyard Haven waterfront – counted between 110 and 120 wooden sailboats and power boats over 20 feet in Vineyard Haven harbor. That’s surely more than any other harbor in the United States, several of the mates agree, except perhaps Camden, Maine. These boats are here because, starting forty summers ago this month, eleven mates came to Vineyard Haven harbor to sail an extreme clipper ship and decided to stay. Other crewmen joined them. And others who never served aboard Shenandoah – but surely knew of her – joined them. They bought wooden boats of their own, and they kept them in Vineyard Haven.

“You end up with a group sticking together,” says Bill Austin. “You end up with wooden boat people sticking with wooden boat people. You end up with various harbors up and down the coast with certain reputations. Padanaram’s got the Concordia yard. By the same token you’ve got Vineyard Haven which, over a lot of years, kept its wooden boat style and heritage. Having Shenandoah sitting there has encouraged that a great deal. Once the harbor has the reputation, if you want a wooden boat, you end up coming to where the wooden boat people are. You end up with Gannon and Benjamin. They don’t work for Bob, but they certainly all work together.”  

One of the mates asserts that, at the start of her fifth decade of service, there’s no longer any reliable way to measure the breadth or depth of Shenandoah’s influence on Vineyard Haven. “I’ve run into I don’t know how many people – hundreds of people – that don’t know anything about boats at all,” says Billy Mabie. “Haven’t been on them other than the ferryboats. But they know Shenandoah’s there and they know which way it’s pointing every morning.”