Captain Douglas awarded for Creative Living

The Black Dog patriarch is awarded the honor, which recognizes efforts to preserve quality of life on the Vineyard.

Captain Bob Douglas with the Shenandoah in Vineyard Haven Harbor. Douglas is the newest recipient of the Creative Living award. -Gabrielle Mannino

Boat builder, restaurateur, and dog enthusiast Capt. Bob Douglas has been awarded the 2020–21 Creative Living award from the Martha’s Vineyard Community Foundation, formerly the Permanent Endowment. 

The Community Foundation announced the award in a press release Wednesday. Douglas was a natural fit for the award, which focuses on encouraging “fine craftsmanship, creativity, and ingenuity,” and recognizes Islanders’ efforts to “enhance and preserve the quality of life on the Vineyard forever.”

In 1964, at 32 years old, Douglas — with no professional boat building experience — moved from Vineyard Haven to Maine, where he began designing and building the 108-foot topsail schooner Shenandoah.

The boat, which would go on to become a staple of Vineyard Haven Harbor, relied solely on the wind. “I wanted to recreate a vessel true to the standard of the best ships that ever sailed under the American flag. I designed each aspect of her to not only achieve this, but also to make her a joy to sail and to live aboard,” Douglas said in the release.

The iconic ship began as a charter schooner, and then as a rite of passage for several generations of Island fifth graders, who used the ship as a classroom to learn about the Island’s maritime traditions and history.

“This award has long been a celebration of the fabric of our community,” said Emily Bramhall, executive director of the Martha’s Vineyard Community Foundation, “and Bob Douglas is a strong and unique thread in that fabric.” 

Douglas’ story began in 1932 when he was born in Chicago. He would spend summers at his parents’ summer house on West Chop. After serving in the Air Force, Douglas began building Shenandoah. In 1967, Douglas brought a black Lab–boxer mix aboard his ship and named her Black Dog, after the character in “Treasure Island.”

Douglas’ trusty canine eventually inspired the Black Dog Tavern, which was built in 1971 and celebrated its 50th anniversary this year. Today, the Black Dog has expanded into a bakery, clothing line, book series, and merchandise.

Speaking to The Times at one of his buildings in Vineyard Haven, as he searched for a drill to repair a fence, Douglas said he’s been happy to give more than 3,000 Island kids a unique experience aboard his iconic vessel. Reflecting on his life, Douglas smiled. “It’s been a perfect lifestyle,” he said. “I’ve been spoiled rotten, and been able to do just what I want to do.”


  1. Next year I would love to see the creative living award go to someone who does the island shuffle every 6 months or so. Someone working a job that doesn’t pay enough to pay their housing, childcare and living expenses. Now that’s creative living.

  2. Sail on Bob and yours are the best thing that happend to Vineyard Haven in my memory…never forget unloading beams off my trailer with Allen Miller and the Lazy Boys construction company. Mutch BUDWIESER and Tammy wynette helping. Hello Black Dog tavern right where it belongs ..looking at the Shenandoah.50 years ago WOWEEEEEE TIME FLIES

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