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  His final mission complete, he put the F86 in the chocks, carefully polished the windshield for the last time, gave the fighter jet a thankful pat and the young Air Force Captain turned and walked away from the 20th century. The year was 1958.
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The man had a dream to step backwards in time. A native of Chicago, he had summered at West Chop on the Vineyard since 1947. From the cockpit of his Vineyard 15 sailboat, he would watch the MV Islander and MV Nobska taking summer visitors back to Woods Hole and New Bedford. He pledged to himself that for him, things would be different. One day he would build a ship. One day he would get a dog to sail by his side and to warm his feet in the winter. And one day he would call the Vineyard home.
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Cotton canvas, manila rope, and marlin along with oak frames and hanging knees, white pine decks, double sawn frames, and masts of Douglas fir, all had to be carefully woven together to satisfy his yearning to live in a different era. Complete with coal stove, kerosene lamps, and hand pumps for water, the new extreme topsail schooner slipped into the icy waters of South Bristol, Maine. It was the 15th of February, 1964, but the vessel modeled after an 1849 revenue cutter looked for like the real thing. A legend was in the making and the Captain was at the helm. The ship would soon be sailing south for Vineyard waters where she would become part of the fabric and lore of this remarkable island.
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The man was Robert Douglas. The ship was Shenandoah, and the pup he would call Black Dog. These three characters are inextricably twined; the schooner has never sailed without her master, not once in over forty years. And for 16 of those years, Black Dog was always on board.
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There was an old seaside inn, part boarding house; part ship’s chandlery sitting on the beach in Vineyard Haven. As fortune would have it, it became available and Captain Douglas walked through the front door and had a look around. From the downstairs library window he could see Shenandoah, swinging on her mooring in the harbor, patiently waiting the new sailing season. The Captain smiled, bought the old house and settled in.
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Life was good. He had acquired a new scamp of a pup, and sailors from all parts of the globe would walk down the beach with their sea bags tossed over their shoulders, headed for the Captain’s house, where Black Dog would greet them at the back door. They eagerly anticipated a gam with the Captain and a dry bunk, if need be. They would sit around the fire and drink coffee, and sometimes rum. They compared ships and captains and talked of cargo and foreign ports.
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By and by, they got hungry. Peanut butter, bacon and honey sandwiches would have to do, or maybe they would make fried eggs, basted in pig fat. These were the house specialties. They were very popular, for there were no year-round restaurants anywhere in town - a terrible situation for hungry sailors. One desperately cold day in 1969, over a bitter cup of coffee and a dry packaged, store bought donut, the Captain had finally had enough. He started sketching on a paper napkin. A small gambrel roofed building started to take shape. He changed the angles and played with the placement of the windows, added dormers, and held it all down with a large red brick chimney. It would look just right on the beach at the head of Vineyard Haven harbor. It would give Vineyarders and visitors a place to meet and eat. The Captain was pleased.
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Excited townfolk helped build and shingle the establishment. Locals were eager to share their recipes for pies, chowders and soups. On January first, 1971, when the doors finally opened, the pies were steaming and redolent of last summer’s berries. Everyone said the chowder was just right, and there wasn’t an empty seat in the house.
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In the corner by the fireplace, the Captain and his dog watched with satisfaction. The food was great, and the fire warmed the room with a glow that only a fireplace can impart. Everyone had helped. The town finally had a heart, and another legend was being made. Captain Douglas named the restaurant after Black Dog. The legacy had begun.
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