Our History

Robert S. Douglas Builds a Boat

captain-douglasCaptain Robert S. Douglas was a jet fighter pilot for the Air Force from 1956 to 58, retiring with the rank of Captain. He first became involved with boats summering and sailing on Martha’s Vineyard as a youth. In the early 1960s, he found himself working on the 83′ Harvey Gamage Shipyard-built windjammer Mary Day, and there hatched a plan to move to the Vineyard, build windjammer, and take passengers back to the days of tall ships and the life of sailing them. His dream came to fruition in the design and commissioning of the construction of Shenandoah in 1964. Based on an original 1850 design of the fast revenue cutter Joe Lane, with the change of line, balance, and sail he created a fast and efficient schooner. The addition of square topsails to the foremast made Shenandoah a truly unique vessel of power and a beauty to behold at sea or mooring. But now that he had his beautiful schooner, he had to have a place to admire her! Not soon thereafter, another schooner found its way to its way to Vineyard Haven. Upon her retirement from the Pilot service in Mobile, AL, Captain Douglas brought the Alabama home with the dream of one day returning her to the sailing form that her famous designer, Thomas MacManus had envisioned. Although it would take over thirty years for this to come about, the fleet that would become the Black Dog Tall Ships was formed.

The Black Dog Tavern

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. Excited townsfolk helped build and shingle the establishment, and were eager to share their recipes for pies, chowders, and soups. On January first, 1971, when the doors finally opened, there wasn’t an empty seat in the house, and The Black Dog Tavern was born. The distinctive graphic element of the tavern’s ‘Black Dog’ also caught attention and became as popular as the menu, and is now seen worldwide on T-shirts, apparel, and many other useful items. Visit The Black Dog web site for a look.

The Coastwise Packet Company

sailCaptain Douglas started the Coastwise Packet Company offering sailing trips and charters on the Shenandoah. He built the offices and the Coastwise Wharf to support his seagoing ventures, as well as to welcome watercraft visitors on extended stay to the Vineyard, or to grab a famously delicious meal at the adjacent Black Dog Tavern. The Coastwise offices are an amazing collection of boats, models, maritime artifacts, and art gathered by Captain