Robert (“Bob”) Douglas, a beloved Island icon who sailed Vineyard seas aboard his tall ship Shenandoah, founded the Black Dog Tavern, and left an indelible mark on the Island, passed away just after midnight Wednesday surrounded by his family and dogs, at his home at Arrowhead Farm in West Tisbury. Douglas, 93, was dealing with an illness prior to his passing, said Andrea Douglas, his daughter-in-law. “We’re at a loss at the moment,” she said on Wednesday morning, adding that Capt. Douglas’ death was a “momentous loss” for the Vineyard.
Douglas is survived by his wife Charlene and their four sons, Rob, Jamie, Morgan, and Brooke.
Nat Benjamin, co-founder of Gannon & Benjamin Marine Railway in Vineyard Haven, told The Times that Douglas had an incredible presence, and was driven by his sensibilities of history and traditional sailing to establish the “gold standard” for everything he did, particularly on the waterfront.
“He was devoted to the history of this waterfront and to create his own history by building a 19th century vessel and then using it to educate anyone who stepped aboard,” Benjamin said of the Shenandoah. “Look what he did for the kids.”
Douglas, born in Chicago in 1932, grew up in Illinois, attended Northwestern University, and served in the U.S. Air Force from 1956 to 1958, stationed at Hanscom Air Force Base in Lincoln, becoming a captain and a fighter pilot before leaving military service. He would also summer on the Island with his family, where he developed his already existing fascination with sailing, unlike his father or brothers.
After serving in the U.S. Air Force, Douglas worked as a deckhand in Maine, where he later constructed the topsail schooner Shenandoah and sailed her to Martha’s Vineyard in 1964.
Douglas launched the Black Dog Tavern in 1971, named after his dog Black Dog, a reference to a character in the adventure novel “Treasure Island” by Robert Louis Stevenson. He established the restaurant to give Islanders a year-round eatery. It has grown into an international brand, but remains a local tavern where many Islanders have cherished memories.
Douglas is widely credited for making the Vineyard Haven working waterfront into a wooden boat mecca of the world, with the Shenandoah standing tall on its mooring and there to greet all who come and go through the harbor.
“I just think it’s a huge loss for our harbor side community,” Ross Gannon, also a co-founder of Gannon & Benjamin, said after pausing for a moment Wednesday in his work restoring a wooden vessel dry-docked in the boatyard.
Douglas’ mentorship is still remembered by the generations of Island children and crewmates who boarded the Shenandoah and the schooner Alabama, which the captain bought and restored in 1967. The program allowed students from fifth-grade classes to sail on a weeklong summer voyage aboard the vessels from another era. For those lucky enough to have had that experience, it has produced memories that will last a lifetime, and will become the living legend of Capt. Douglas.
Doug Cabral, former MV Times editor and author of the book “My Shenandoah: The Story of Captain Robert S. Douglas and His Schooner,” had a front-row view of the impact that Douglas had on his crew and Islanders. Cabral worked on the Shenandoah under Douglas, after first seeing the vessel in 1968 while working in a Fairhaven shipyard.
“It may be that only a few of us kids ultimately led their adult lives going to sea for a living, but for sure it was a rare few who left the schooner unaffected,” Cabral posted on Facebook in a tribute to his longtime friend. “The hallmark of Bob’s natural, quiet leadership was his unmistakable commitment to the value of the complicated, engineless sailing experience because of its obvious exigency and demanding discipline. He infiltrated a bit of his focused, undiluted vision in each of us. Now, his watch on deck [has] ended, I am reminded of the hours I spent talking with Bob, who then was approaching 90, about himself and Shenandoah, his life’s obsession, as I wrote my story of his life.”
One of those kids was Ian Ridgeway, the current captain of the Shenandoah, and former first mate under Douglas. He first boarded the Shenandoah as a Tisbury School fifth grader. “He’s been a mentor and a father to me, and a good friend. One of my best friends,” Ridgeway said.
Ridgeway and Casey Blum are continuing Douglas’ educational legacy with their programming at the Martha’s Vineyard Ocean Academy, to which Douglas donated the Shenandoah.
Ridgeway said beyond vessel skills, one of the most important lessons imparted by Douglas was being an upstanding citizen: taking care of other people, yourself, and paying attention to your surroundings.
“He’s had a really tremendous and profound impact on so many people,” Ridgeway said.
Christian Cabral, a team member at Gannon & Benjamin and a family friend of the Douglases, attested to Capt. Douglas’ mentorship as well.
“I worked for Robert starting at a pretty young age,” Cabral said. “It was a formative experience. He is a remarkable person who kind of constructed the world he wanted to live in and then, for those of us who shared similar interests, he allowed us to share in that world. It was sort of a once-in-a-lifetime experience for me.”
Douglas left an enormous footprint on the Island, and, as former MV Times writer Geoff Currier put it in a 2022 profile, “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.”
Douglas’ humility toward his impact on the Vineyard showed when he was the recipient of the 2021 Creative Living Award, which is awarded by the Martha’s Vineyard Community Foundation to people who made significant contributions to the Island’s quality of life.
“It’s nice, but I don’t deserve it. I just did what I like to do,” Douglas said at the time.
Douglas was a light that attracted people to the Vineyard Haven, said Nat Benjamin, who ducked into the newsroom just behind his Marine Railway on Beach Road. Benjamin said he felt the best way to honor Douglas’ legacy was continuing his work to keep the harbor a working waterfront.
“He was sort of the beacon on the hill that got the rest of us really together,” Benjamin said. “We saw the standards he had set and the goals he had set, and we kind of jumped on the train and tried to keep it moving. Bob was very committed to setting this harbor up so there’s a real infrastructure to maintain it, so the work can be done right here.”
Benjamin told The Times that Douglas’ success was “unequivocally” supported by his wife and children, and that all of his work would not have been possible without them.
You would be hard-pressed to find anyone more devoted to the history and tradition of Martha’s Vineyard Island, than Captain Robert Douglas. He rarely left the island, other than at the helm of one of his many boats, and had an encyclopedic knowledge of MVI and the Elisabeth Islands nearby. As a devoted World traveller, I find it fascinating that he found his place in the World early on, and was content to live within a few miles of his Tavern, Wharf, and Grey Shed for most of his life. He had a full life, and died in his own home – exactly as he would have wanted it. Vale, Robert – your legacy will be remembered forever.
Sailing on Shenandoah with Capt. Douglas was an unforgettable experience for hundreds of mariner scouts from Wilmette, Illinois over many decades. I’m so grateful for those weeks spent on Shenandoah. He left quite a legacy. Sincere condolences to his family.
When Bob saw our attempt to replicate an 18th C. Cape across from Nip ‘N Tuck in 1970, a knock came at the door one evening. It was Bob, who handed me a big beautifully hand wrought 18th C. iron door handle and latch. He simply said: “I thought you might like this for your door.” Thanks Bob. You INSPIRED us, by land and by sea, with your kindness.
Rest in peace Captain….. the island will never quite be the same.
Our Doah crew are still close friends… will never forget Capt. Bob!
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