Captain Robert “Bob” Douglas, a beloved Martha’s Vineyard icon, has passed away. Known for sailing his legendary tall ship, Shenandoah, Douglas was also the visionary founder of the Black Dog Tavern, eventually inspiring the popular brand Black Dog Apparel.
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The famous sailor died on April 23, surrounded by his loved ones and cherished dogs, at his home on Arrowhead Farm in West Tisbury, Massachusetts, per The Vineyard Gazette.
Douglas, 93, had been battling an illness before his passing, his daughter-in-law, Andrea Douglas, told The Martha Vineyards Times.
So saddened to hear of Captain Robert Douglas Sr.’s passing. He was the heart and soul behind The Black Dog—an iconic piece of New England life. I’m grateful for the memories, from proudly wearing the brand to collaborating with his wonderful team over the years. My thoughts are… pic.twitter.com/p2Wp7tHybi
— ▼ Kiel James Patrick (@KJP) April 25, 2025
Douglas, born in Chicago in 1932, grew up in Illinois, attended Northwestern University, and served as a captain and fighter pilot in the U.S. Air Force from 1956 to 1958. He spent summers on the Island with his family, where he cultivated a passion for sailing.
After his service in the U.S. Air Force, Douglas took up work as a deckhand in Maine. There, he built the topsail schooner Shenandoah and, in 1964, sailed her to Martha’s Vineyard.
In 1970, Douglas married Charlene Lapointe, a fellow sailor and former leader of the Mariner Scouts, a waterborne Girl Scout program. Today, Charlene runs Arrowhead Farm, where she boards horses and teaches riding lessons to students of all ages. Together, they have four sons—Rob, Jamie, Morgan, and Brooke—and are proud grandparents to six grandchildren.
Robert S. Douglas Founds Black Dog Tavern
In 1971, Douglas opened the Black Dog Tavern, inspired by his beloved dog, Black Dog, and the character of the same name from Robert Louis Stevenson’s Treasure Island. His vision was to create a year-round gathering spot for Islanders, offering both comfort and community. Over the years, the tavern has grown into an international brand but remains a beloved local landmark, cherished by many Islanders.
The mail-order business started in the late 1980s when the company introduced a catalog featuring T-shirts, mugs, cookie tins, and posters, all listed on a single sheet of paper. The simplicity of the Black Dog logo quickly gained attention.
The logo gained widespread recognition, adorning clothing and accessories popular among both locals and tourists nationwide. Even high-profile individuals, including President Bill Clinton, were spotted wearing Black Dog merchandise, further cementing its iconic status.
The business soared in 1991 when Rolling Stone deemed its emblem stylish, featuring a photo of three young ladies wearing sunglasses and long-billed Black Dog caps.
Douglas is also widely celebrated for transforming the Vineyard Haven working waterfront into a global hub for wooden boats. With the majestic Shenandoah anchored proudly at its mooring, it stands as a timeless symbol, welcoming all who pass through the harbor.
Douglas leaves behind his wife, four sons, and their families.