Martha’s Vineyard changed forever when Capt. Robert S. Douglas sailed his custom-built, 108-foot topsail schooner Shenandoah into the Vineyard Haven harbor in 1964.

Not only did a small port seven miles off the Massachusetts coast transform into a worldwide mecca for wooden boat builders, but it touched the lives of more than 5,000 Island school children, who have learned — and continue to learn — the art of sailing on weeklong trips aboard the legendary vessel.

Surrounded by dozens of those very boat builders, sailors and school children, in the harbor he has called home for a half-century, Captain Douglas received the 38th annual Creative Living Award from the Martha’s Vineyard Community Foundation in a swashbuckling, joyous ceremony Monday night at the Gannon and Benjamin Marine Railway.

The award is given to an Islander who has contributed significantly to the quality of life on the Vineyard through creativity and spirit, and everyone agreed that Captain Douglas — a devil-be-damned, pony-tailed mariner whose boats and Black Dog business reawakened a once bygone seafaring era — represented the worthiest of winners.

Isabelle Lew, Emily Bramhall and Captain Bob. — Ray Ewing

The only question was why it took so long.

“Bob could have been the first recipient,” laughed wooden boat builder and former Creative Living Award recipient Nat Benjamin on Monday night. “It’s about time.”

Originally scheduled for a Zoom event in 2020, the man who had made his name eschewing fiberglass convinced the Community Foundation to eschew fiber optics as well, postponing the festivities to an in-person date in 2021.

With the Gannon and Benjamin boatyard sawdust speckling the evening sun and a full moon rising over the Vineyard Haven harbor, that wish became a reality on Monday, replete with an oyster hour, storytelling, toasts and a 12-minute movie honoring the life and work of Captain Douglas.

The ceremony began at dark, with emotional remarks from Community Foundation executive director Emily Bramhall, followed by the film screening. Made by Ollie Becker of the Martha’s Vineyard Film Festival when the event was still planned for Zoom, the film, with footage old and new, told Captain Douglas’s story through his various first mates and proteges, describing his own journey from a 15-year-old West Chop kid to his time as an Air Force jet pilot to his work in Harvey Gamage’s Boatyard.

Matthew Stackpole and Nat Benjamin gave tributes. — Ray Ewing

Always a dreamer, Captain Douglas hatched a scheme to design and commission the Shenandoah as a vehicle for his life on the water, adapting the drawings himself from an original, 1850 revenue cutter. After its completion, he brought the boat to the Vineyard Haven harbor. There were no schooners in the harbor when Captain Douglas arrived in 1964. There are now 11.

Former first-mate Matthew Stackpole said that if Jon Wilson were to start Wooden Boat magazine today, he would start it in Vineyard Haven.

“People make pilgrimages to see Bob,” Mr. Stackpole said Monday. “He’s a guru. It’s amazing. It’s like coming to Mt. Olympus.”

In the video and in their toasts, former mates and mariners regaled the approximately 40 people in attendance with stories about Captain Douglas’s international renown. They spoke about the fear he inspired in other boaters when they saw him on their vessel with a tape measure in hand. They spoke about the uncanny attention to detail in Shenandoah, the diamonds on the vessel blocks and the unique starboard side. They spoke about how he rarely let anyone else take the helm, and how a job on the Shenandoah was the ticket to a job on any boat in the world.

“That’s a reflection of the respect that Bob had,” Mr. Stackpole said. “No finer person could receive this award...congratulations, my captain. Well done.”

Three cheers down at the boatyard. — Ray Ewing

Captain Douglas listened with his wife Charlene, children and grandchildren by his side, his salt-crusted Coastwise Packet Co. hat jaunty atop his head.

Mr. Benjamin and Mr. Stackpole said that it was Captain Douglas and the Shenandoah who brought them to Vineyard Haven. But both agreed that it was his transition to chartering children, rather than adults, that marked his greatest moment.

Over the past three decades, almost every Island fifth-grader has gotten a chance to spend a week on the Shenandoah. Although Captain Douglas has since passed the boat on to a nonprofit organization called FUEL to continue the trips and education programming, he still spent two weeks on the water this summer, at the age of 88.

“There is nobody who has lived as creative a life as Bob,” Mr. Benjamin said. “You’ll never get old if you keep sailing. You’ll get old if you stop.”

Captain Douglas, ever the raconteur, then provided his own narrative, describing his journey as a “continuum” that began with summers on the Island and proceeded from the purchase of his first Peapod wooden boat to the day in 1964 when the keel went in the Shenandoah. By the time he got to the 1970’s, the entire audience felt like fifth graders once again, listening to Captain Douglas  tell tales on the Shenandoah under the stars, long into the night.

Event took place, fittingly, at the Gannon and Benjamin Marine Railway. — Ray Ewing

“The bottom line, the most important part of this gathering, is that I’m just passing through," Captain Douglas said. "I’m just lucky that I’ve gotten to do exactly what I’ve wanted to do in my life. But the best part is what’s happened in Vineyard Haven. It’s turned into a remarkable place.”

As Captain Douglas’s other schooner, the Alabama, sat in the harbor, its Black Dog flag flying high, he credited his work with children and young people for keeping the continuum alive.

“We live in a time warp,” he said. And in characteristic fashion, he spoke at length about the magic of the Vineyard waters — a place that he believed had the best sailing conditions of anywhere in the world.

Mr. Douglas spent his life ensuring it had the best boats, too.

“If you had Paul Bunyan and the world’s biggest bulldozer to make this coastline, you couldn’t have done any better,” Captain Douglas said. “This is God’s world, right here, on the Vineyard. I’ve seen Bangkok, and I’ve seen Paris, and I’ve seen a few places in between. But you can’t do better than here.”