The story of how one man's dream of a simpler time became a reality.
At an early age, Robert Douglas escaped the hustle and bustle of his hometown Chicago by summering on the Vineyard. From the cockpit of his fifteen-foot sailboat, he would watch the MV Islander and MV Nobska ferry visitors back to Woods Hole and New Bedford. In 1958, Douglas flew his last mission as an Air Force Captain, then walked away from the noise and trappings of the twentieth century and moved towards the life that would become his legacy.
Douglas constructed a vessel for himself, modeled after the schooner Joe Lane, an 1850 revenue “cutter”. Wherever possible, Captain Douglas would incorporate materials and techniques used in the 19th century. When it was finished, the Captain was at the helm of his very own boat, a one hundred and fifty one foot topsail schooner christened the Shenandoah, en route to its new home in the Vineyard.
In 1967, he brought a black lab/boxer mix aboard and named her "Black Dog” after the character in Robert Lewis Stevenson’s “Treasure Island”. For sixteen years, the man, the boat, and the dog were nearly inseparable.
Life was good for Captain Douglas. He purchased an old seaside inn that sat on the beach in Vineyard Haven. From the downstairs library window he could see Shenandoah, swinging on her mooring in the harbor. Sailors from all parts of the world would walk along the beach, their sea bags tossed over their shoulders, headed for the Captain’s house. Black Dog would greet them at the door. The Captain and the sailors would sit around the fire and drink coffee, sometimes rum. They compared ships and captains, and talked of cargo and foreign ports.
Summers were busy as people flocked to enjoy the island, but winters were lonely. In fact, the island didn’t even have a single year-round restaurant. One cold day in 1969, the Captain mulled over his bitter coffee and dry, store-bought donut and decided that enough was enough. He began to sketch out an idea on a napkin, dreaming of a place where Vineyarders and visitors could enjoy a good cup of chowder and great conversation year-round.
On New Years’ Day in 1971, the Black Dog Tavern opened its doors for the first time. The chowder was just right, and there wasn’t an empty seat to be found. In a corner by the fireplace, the Captain and his dog watched with satisfaction. The food was perfect, and the fire was warm.
And so a legacy began.