No man is an Island

But Capt. Bob Douglas comes pretty close.

Capt. Bob Douglas has made a lasting contribution to the Vineyard Haven waterfront. — Gabrielle Mannino

Updated: 1/21

Capt. Bob Douglas has navigated a life with little precedent. His tall ships, the Shenandoah and the Alabama, have become the signature pieces of Vineyard Haven Harbor. His “week at sea” sailing programs have touched the lives of thousands of kids on the Island. The Black Dog restaurant, which he conceived of and created, is recognized around the world. 

And yet, to see Douglas, with his weathered face, rumpled khakis, and ball cap pulled snugly down over his head, or to see him driving around town in his beat-up Ford pickup truck, you know that there isn’t a pretentious bone in his body.

Recently, Capt. Douglas was presented with the 38th annual Creative Living Award by the Martha’s Vineyard Community Foundation, and it gave us a chance to reflect upon Douglas’ life, and what an enormous impact he’s had on Martha’s Vineyard. 

In her opening remarks at the presentation, Emily Bramhall, executive director of the foundation, said, “There is no doubt that Capt. Robert Douglas has enhanced and preserved the quality of life on the Vineyard. Over many decades of dedication, passion, and hard work, Bob has embodied the very best of what this Island represents, sharing so generously his vision and life’s work with the Island community, which in turn, has embraced it as its own.

 “The Vineyard Haven Harbor that we know today, known worldwide as a wooden boat mecca, had its roots with the arrival in 1964 of Capt. Douglas’ Shenandoah. Her arrival ushered in an era of sailing and wooden boatbuilding and appreciation that continues to this day.”

This would be a remarkable achievement for anyone, let alone someone who grew up thousands of miles from the smell of salt air. “Bob was a Midwestern guy,” said Doug Cabral, whom I spoke with at his home in West Chop. Cabral is the former editor of The MV Times, longtime friend of Douglas, and author of a biography on Douglas which will be released in the spring.

Douglas was born in 1932, grew up in Illinois, and went to Northwestern University. And neither his father nor his brothers expressed any real interest in boating. “What he did was unusual, maybe unique,” Cabral said, “if you look at his background and the nature of his family, and the fact that all his schooling took place in the Midwest or West.”

But in 1947, when Douglas was 15, the trajectory of his life would change when his father leased a house on the Vineyard for the summer and rented a sailboat. Douglas had found his passion. And yet, ironically, while attending Northwestern, he enrolled in ROTC, and after graduation he enlisted in the Air Force, which may sound like light years from sailing ships. But he gives credit to the Air Force for somehow bringing him closer to the water. 

Douglas was stationed at Hanscom Air Force Base in Bedford, which allowed him to spend off time on the Vineyard. Douglas attained the rank of captain as a fighter pilot, and he moved to the Island in 1958 after walking away from his downed F-86 Sabre jet.

Douglas would have several small sailboats over the next few years, but he was interested in learning about and sailing something larger, so in 1960 he went to Maine and signed on as a deckhand on the 115-foot, two-masted schooner Stephen Taber.

“Bob never had any sailing training,” Cabral said. “But he associated with people who knew sailing well, and he sucked up that knowledge.” Douglas began working at the Harvey Gamage shipyard in South Bristol, Maine, and as he immersed himself in the art of the shipwright, he began drawing up plans for the Shenandoah.

In a film produced for the Creative Living Award by Ollie Becker of the Martha’s Vineyard Film Festival, various former Shenandoah crew members spoke of Douglas and his vision and approach to work. “With Bob, it was traditional or nothing, there was no halfway,” Nat Benjamin, principal at the Gannon & Benjamin Marine Railway, said. 

“Bob had a vision, something he wanted to do, and he made it happen,” Bill Mabee, a former mate on the Shenandoah, said. “There was nothing modern about the Shenandoah, there was no engine — kerosene lamps, coal stove — the rigging was all primitive, it was all historically accurate.”

“When Bob moved to Maine to work with Harvey Gamage on the Shenandoah,” Cabral said, “he and Gamage had their share of disagreements. When Bob wanted the wood to be better than what Harvey was offering, Gamage said, ‘I just can’t suit you,’ in the sense that he couldn’t make things like Bob wanted them, so to stop pestering him.”

There isn’t an ounce of compromise in Robert Douglas.

While in Maine, Douglas not only learned the craft of designing, building, and sailing schooners, he also learned the basics of the chartering business, and dreamed that he could eventually bring the Shenandoah to the Vineyard and charter her.

There was no shortage of schooners off the coast of Maine in the first part of the 20th century. They were used for shipping cargo, but Cabral explained to me that with the advent of trucks and railroads, many schooners were reduced to languishing in the harbor, and later they were used for taking out passengers for day cruises. “Bob could have had his choice of many schooners for around five grand,” Cabral said, “but Bob wanted to have things just the way he wanted them. And he had resources — his father was descended from the family that started Quaker Oats.”

Ever the traditionalist, Douglas designed the Shenandoah without an engine, like the bulk of the classic Maine schooners. When not under sail, the Shenandoah was propelled by a yawl boat. The Shenandoah was only the second boat in the Maine schooner fleet that was built purposely for taking passengers.

So it was with a great deal of excitement and some trepidation that Douglas set sail for Martha’s Vineyard in 1964, determined to make chartering the Shenandoah his livelihood. As he rounded East Chop entering Vineyard Haven Harbor, onlookers were dazzled by a 154-foot topsail schooner under full sail, but they could hardly imagine the impact that Douglas and the Shenandoah would have on the harbor in the years to come.

Right from the beginning, one can imagine the reaction of people sailing into Vineyard Haven Harbor on the ferry and seeing this magnificent square-rigged creature either at anchor or underway.

“It spoke to a lot of people,” Cabral said. “It made a big impact on people who ordinarily lead normal lives.” And the impact grew even greater when, in 1967, Douglas purchased and restored the Alabama, a 90-foot gaff-rigged schooner which he also moored in the harbor. The Alabama was built in 1926, and served as the pilot boat for Mobile, Ala. The two ships laying tall and proud in one place was something to behold.

Douglas also had a hand in convincing the shipbuilders Ross Gannon and Nat Benjamin of Gannon & Benjamin to set up shop on Vineyard Haven Harbor, which would lead to the proliferation of even more beautiful wooden boats over the years. 

I spoke with Nat Benjamin outside the G&B yard, and he told me how he happened to settle in Vineyard Haven. “When we sailed into Vineyard Harbor in 1972,” he said, “we were looking for a place to start a boatyard, and we saw the Shenandoah and the Alabama, and it just seemed natural for us to stay here. It was the perfect match. 

“But when we told people we wanted to build wooden boats and have a marine railway, they said, ‘You’re nuts, it’s not going to happen.’ But then we talked to Bob, and he said, ‘Of course it will happen, do it.’”

“There are other pockets of wooden boats around today,” said Emily Bramhall in a phone conversation. “But Vineyard Haven Harbor is really the jewel in the crown. When the Shenandoah first arrived in 1964, there were only two schooners in the harbor — today there are around 14.” 

In fact, when you look around the harbor today, virtually every boat is a sailboat. That’s how much the seascape of Vineyard Haven Harbor has come to reflect Capt. Douglas’ passion.

But it’s not just an aesthetic change that Douglas has brought to the Island.

In the mid-’80s, Douglas made the decision to reach out to the Island’s youth, and invite every fifth grader to spend a week at sea on the Shenandoah or the Alabama. “It may have been his greatest moment when he transitioned to taking kids out,” Benjamin said. 

In the video, Lynne Whiting, a former schoolteacher at the Chilmark School, describes what it was like when she accompanied kids on the Shenandoah the first time. “Stepping on the Shenandoah, I had a sense of history that struck me immediately — no auxiliary power, no gadgets, video games, no TV, no radios. It was a refreshing switch to immediately become part of a team. You’re responsible for raising sails, lowering sails, taking care of the food, the cleanup … It was an incredible experience for me as an adult. I just had a sense of optimism for the kids coming onboard with me, thinking they would have something for the rest of their lives.”

Casey Blum (LCSW), one of the kids who sailed on the Alabama and is now the program director at FUEL, said, “Most people on the Island probably don’t realize that Bob Douglas and his family have taken over 5,000 Island kids sailing for a week. So much of what he’s created with the ship is like a culture, and he’s invited people to be part of that culture, and helped a lot of young people to find their identities.”

Not all of Douglas’ accomplishments are related to the sea. The Black Dog Tavern, which he started in 1971, had a positive effect on Island life as well. The restaurant was inspired by Douglas having breakfast with builder Allen Miller and lamenting the fact that there wasn’t a good place to have breakfast or a good cup of chowder in Vineyard Haven. Douglas drew up plans for the restaurant on the spot on a napkin, and commissioned Miller to build the Black Dog Tavern, which he named after his own dog, Black Dog, a character in Robert Louis Stevenson’s “Treasure Island.”

“There were very few good restaurants around at the time,” Bramhall said, “and the Black Dog not only offered good food, it served as a community gathering spot. Tradespeople would come together in the morning for breakfast; they had guest chefs, and different cuisines. The rustic interior, with its great fireplace, might as well have been in a museum. In a sense it was all part and parcel of the Shenandoah; it reinforced the Island’s maritime tradition.”

Bob Douglas is approaching 90 years old. He’s stepping away from the Shenandoah, and while he took a few cruises with kids in the summer of 2019, the boat is now in the hands of FUEL, an acronym for Foundation for Underway Experiential Learning, which is run by two Douglas protégés, executive director Ian Ridgeway and Casey Blum. The organization is aimed at helping young people overcome their difficulties while at sea. Douglas serves as chief advisor for FUEL. 

Looking back over the past 50-plus years, Bob Douglas has had a pronounced impact on the Vineyard harborscape, promoted Vineyard Haven’s rich maritime culture, influenced thousands of young people’s lives, and created a restaurant that became a focal point for the community. And you could say it all began with the Shenandoah.

“Bob Douglas doesn’t get enough credit for the fact that he saved the town,” said Trip Barnes, an Island community leader. “He’s a class act. And if the town of Tisbury had to come up with a new masthead, the Shenandoah should be on it.” 

And from Douglas’ perspective, at the Creative Living award ceremony he told the assembled crowd, “I’m the luckiest person ever. I’ve done exactly what I wanted to do.”


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