Capt. Robert Douglas receives Creative Living Award

Black Dog founder is honored during M.V. Community Foundation awards night. 


A large crowd gathered at Gannon & Benjamin Marine Railway in Vineyard Haven to celebrate Capt. Robert Douglas, the winner of the 2020–21 Creative Living Award. The event was hosted by the Martha’s Vineyard Community Foundation and featured food, drinks, and recollections of the vast contributions to the community made by Douglas.

“Robert is joining an illustrious crew,” Emily Bramhall, executive director of the foundation, said of the Black Dog founder. “Holding a Zoom event just did not sit square with the nature of our recipient, so we waited patiently until we could all be together.”

According to Bramhall, the decision to honor Douglas was decided more than a year ago, but they had to wait 16 months before giving it to him because of the ongoing pandemic. 

According to the foundation’s website, the Creative Living Award was established in 1983 when what was then known as the Permanent Endowment received a $60,000 donation from Island resident Ruth J. Bogan. Bogan requested that a portion of the donation be used to “encourage fine craftsmanship, creativity, and ingenuity in many fields through such awards as gifts, prizes, and scholarships,” which led to the formation of the Creative Living Award. The Creative Living Award recognizes people who “contributed significantly to the quality of life on the Island.”

A short video about Douglas was filmed to show attendees, though it was delayed briefly due to technical difficulties. The film showcased Douglas’s deckhands talking about his vision of bringing the Shenandoah, the 108-foot schooner Douglas designed, to life during a time when working 19th century wooden ships were essentially gone from the American seas. The deckhands also spoke of his character — his eccentricities, his drive, and his kindness. 

“It could only come from a mind like his that dreams,” Ian Ridgeway, current captain of the Shenandoah, said in the video. 

Bramhall said the film will be available to view online in a few days. 

Matt Stackpole and Nat Benjamin, former first mate of the Shenandoah and co-founder of the marine railway respectively, stepped up to speak about Douglas during Monday’s event. In a mixture of comedy and sentimentality, the two men spoke about the contributions made by Douglas to the Vineyard Haven waterfront.

“One of the reasons we’re both here is because of Robert Douglas,” Stackpole said, indicating Douglas’ vision of setting up a wooden boat yard where the railway is now. “I had the good luck of him lowering his standards and hiring me as a deckhand in 1966.” 

“No finer person could receive this award, in my opinion,” Benjamin said.

Stackpole said Douglas also received the Lifetime Achievement award from Tall Ships America for “his exceptional impact on traditional sailing.” 

Douglas and the Shenandoah have become synonymous with the return of functional wooden boats. Stackpole said many people interested in boats come to Vineyard Haven to meet Douglas. The Shenandoah arrived in Vineyard Haven from Maine in 1964, and it made the village into a “wooden boat mecca,” according to Bramhall. 

“Her arrival ushered in an era of sailing and wooden boatbuilding and appreciation that continues to this day,” Bramhall said of the Shenandoah.

The Shenandoah has also been used for a children’s program where fifth graders across the Island experience a week aboard the vessel — an experience which brought many happy memories for those who participated. It also provided a guiding vessel for young deckhands still searching for their own life’s path. Bramhall called Douglas a “strong and unique thread” in the fabric of the Island community, which was followed by cheers and applause.

The night concluded with Douglas receiving the award, which was in the form of a rock on a pedestal. Isabelle Lew, the foundation board’s chair, said the rock used to stand for permanence. Now, it represents “the rocks of our community.” He also received a check for $1,000.

Douglas also spoke of his life’s journey after receiving the award. A Chicago native, Douglas spent many summers at his parents’ seasonal home in West Chop. After his service in the Air Force, Douglas went to Maine to build the Shenandoah despite no prior experience with boatbuilding. Douglas thinks the catalyst was a 28-foot boat his father allowed him to buy as a high school graduation present. One thing led to another, like a “link on a chain,” Douglas said of his life’s journey. 

“I’ve been a very lucky guy to do what I want all my life,” Douglas said. “I don’t know many people who could fall in line and say that. Even my three years in the Air Force, I would do it again.” 

Asked how he felt about receiving the honor, Douglas told The Times, “It’s nice, but I don’t deserve it. I just did what I like to do.” 


  1. I am humbled and honored to have been part of this celebration of Captain Douglas, an important player in the Vineyard’s maritime history. I may have grown up at the foot Mt. Olympus in the Rocky Mountains of Utah, but my adult life was forever changed when I set foot on Shenandoah. Thank you to all of the families of fourth and fifth graders at Chilmark School who participated in our yearly journey at sea with Captain Bob!

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