The story of how one man's dream of a simpler time became a reality.



Robert Douglas is born in Chicago, and spends his childhood summers escaping the hustle and bustle of the city at his parents' summer home in West Chop. He spends his summer days watching the Vineyard ferries traversing the waters between the island and the mainland from his perch aboard his 15-foot sailboat.

Captain Robert Douglas joins the Air Force, and flies his last mission as a jet fighter pilot two years later in 1958. After ejecting from a malfunctioning jet, the Captain walks away from the noise and trappings of the 20th century and moved towards the life that would become his legacy.


Captain Douglas makes a vessel for himself, using early construction techniques and materials wherever possible. The Captain christens his new topsail schooner "The Shenandoah", and brings her to her new home on the Vineyard.


The Captain brings a black lab/boxer mix aboard and names her "Black Dog" after the character in Robert Lewis Stevenson's "Treasure Island". The man, the boat, and the dog are nearly inseparable.


The Captain purchases an old seaside inn in Vineyard Haven, where he and the dog play host to sailors from all over the world. They sit by the fire, sharing drinks and stories. Summers are busy, winters are lonely.


After dreaming of a place that Vineyarders could enjoy year-round, the Captain builds the Black Dog Tavern. The Tavern opens its doors on New Year's Day, and ever since, folks have flocked to its tables to enjoy the perfect chowder and a cozy seat by the fireplace.

Learn more about the history of The Black Dog by watching our Legacy video, featuring footage of The Black Dog Tavern and Tall Ships, historic photos, and stories told by Captain Douglas's sons.