Sending off Capt. Robert Douglas

On Friday, the dock outside the Black Dog Tavern teemed with wooden sailboats, and the tall ships Shenandoah and the Alabama, as friends, family, and Islanders gathered at the wharf to celebrate Capt. Robert Douglas, who died in April at the age of 93. 

On the docks, relatives and fellow crewmembers told of Douglas’ entrepreneurial and adventurous spirit; there were bagpipes and cannons fired, a ceremonial biplane flyover, music, toasts, and heartfelt nods to the Island icon and the lasting impact that he has had on the Vineyard.

Douglas is the founder of the Black Dog Tavern, built and maintained the Shenandoah, and left an indelible mark on the Island.

Douglas’ son, Rob Douglas Jr., was the first to speak on Friday, welcoming attendees who had gathered on the dock, and sharing the love and respect he had for his father.

“Growing up with Dad was a pretty wonderful experience,” Douglas Jr. said. He recounted how as a young boy, instead of traditional bedtime stories, his father told him about local shipwrecks, the stories accompanied with paintings and prints of vessels around their home on Arrowhead Farm in West Tisbury. 

“That was pretty heavy stuff for a 7-year–old, let me tell you,” Rob joked, who said that he would often ask his father to promise that they would never have a shipwreck. “I often looked at Dad at the wheel, and I never saw fear, I only saw a calm presence, mostly quiet, but always in control.” 

He said that that courage was on display in the last days of his life. “As Dad was passing this spring, I never saw a hint of fear, I never saw a tear. What I saw was pure courage, another great lesson from a dad to a son that I am hoping that I’ll be able to replicate when my time comes,” said Rob.

Capt. Gary Maynard — who worked on the Shenandoah at 16 and made his way up from galley boy to deckhand, mate, and to captain, and was even married on the tall ship — gave an emotional speech on the impact Douglas had on him and other Islanders.

“Martha’s Vineyard lost an irreplaceable elder,” Maynard said. “Bob was first my captain, then a mentor, then a collaborator, and then, for decades, my friend. We always had something to talk about right up until his last days.” 

Maynard credits Douglas for Vineyard Haven’s vibrant waterfront. He showed how the harbor possesses the largest fleet of wooden boats in the country, beautiful schooners, an active wooden boatyard, riggers, shipwrights, yachtsmen, merchant captains, mates, and pilots. They all started their careers aboard Capt. Douglas’ boats, he said. He also spoke to the importance of the Shenandoah, which he noted was the last square-rigged vessel built at a commercial shipyard in the country, built in the final moments before the historic resources that made her possible were gone forever. 

“Shenandoah was not a replica; she is the last American sailing vessel; she is an irreplaceable artifact of tremendous value,” said Maynard. “Through force of will and strength of character, Bob Douglas maintained those threads of knowledge passed down from generation to generation since men first took to sea.” 

Not only did Douglas influence aspiring sailors, boatbuilders, and historians, he also gave thousands of schoolchildren a glimpse into the 19th century, one week at a time, aboard the Shenandoah, which Maynard believes is his most enduring legacy. “Bob Douglas was a masterful sailor and an unequaled keeper of the flame in the final moments of the sunset in the great age of sailing,” Maynard said. “Robert S. Douglas was a truly remarkable man, a great man, a man who by being true to himself and living his own unique way touched the lives of literally thousands of young people, and he profoundly influenced our community in ways we see all around us today.” 

After the eulogies, guests were invited to share memories; many recalled their experience as young children aboard the Shenandoah, and the profound and lasting impact that experience had on their lives. Shenandoah’s shantyman, Billy Schustik, delivered a rendition of “Oh, Shenandoah,” a shanty. As he began singing, a low hum spread throughout the crowd as people slowly joined in. “Oh, Shenandoah, I long to see you. Away, I’m bound away, ’cross the wide Missouri,” the audience sang as cups were passed around for a toast. 

As dusk rolled over the harbor, bagpipes were played aboard the Alabama, and cannons were shot off from the Shenandoah. Charlene Douglas, Capt. Bob’s wife, was presented a flag for  Douglas’ service in the Air Force, and a small bonfire began on the beach in front of the Black Dog Tavern. Guests filed off the tall ships and down the dock toward land, each with a piece of Capt. Bob’s legacy.