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When Sailing Came to the Bay

It wasn’t so long ago that boating shifted from a way to earn a ­living to a sport and pastime

With sailing the rage all over the Chesapeake, waterfront communities organized sailing clubs, fleets and regattas for sport and competition.
    The Annapolis Yacht Club — in our times embarking on a $10 million expansion — reorganized in the late 1930s, after World War I and the Great Depression nearly put the venerable club out of business. The club was founded in 1886 and thrived in the first decade of the new century with races and regattas for small sailboats, canoes and shells.
    (The much newer Eastport Yacht Club was founded in 1980.)

A lot has changed at the Annapolis Yacht Club since the days before World War II, when, boats like the home-made Miss Fortune (second from bottom, above and shown below during construction) were common sights. Below, Les Trott, smoking a pipe, and Murray Davis work on Miss Fortune, a Hampton No. 65.

    At 95, Annapolitan Lester Trott, an Admiral of the Chesapeake and lately named a city Living Landmark, is the oldest and longest-standing member of the Annapolis Yacht Club, where he raced with enthusiasm if, he says, not much success before and after World War II.
    Small boats were, he says, “the thing back then, not the big cruising boats that race today.” Hamptons and Starboats were his boats of choice, and he had one of each.
    The Hampton he and a high school friend built from a kit from the Virginia manufacturer. No. 65, an 18-footer, “was very comfortable and good looking,” Trott recalls.
    “But,” he says, “we called her Miss Fortune because we made mistakes in building so we were not competitive like boats built by pros.
    “I lost my edge and became a social sailor,” Trott says. “But it was still a lot of fun.”
    Farther south, at West River Sailing Club in Galesville, sailors competed fiercely with, among others, sailors from the Fairhaven Club that hoped to rescue the Alice E. (See next page.)
    In the 1930s and ’40s, Ernest ‘Captain Dick’ Hartge — of the legendary boat-building family of Galesville — designed many of the boats sailed and raced by that generation: the Albatross, Sea Witch and Chesapeake 20;
    The Hartge family and Chesapeake 20s “bridged the traditions” of Chesapeake Bay boating, according to Jeff Holland, former director of the Annapolis Maritime Museum in Eastport and current director of Captain Avery Museum in Shady Side. You can see a restored Chesapeake 20, the Vanity, on display at Captain Avery Museum.
    The Hartges, Holland said, “took the same tradition of craftsmanship they applied to building working boats for the seafood industry and applied it to building pleasure boats for playing on the Bay.”
    The Chesapeake 20, “will go like a scared cat in a breeze,” Hartge claimed in a 1940s advertisement. That was the point, for he designed the boat to win races against other sailing clubs.
    World War II took the sailors out of the sport.
    By the summer of 1947, veterans were back on the water. They were more fearless than ever, judging by a Coast Guard complaint and the response of Fair Haven Sailing Club commodore Robert Ray.
    The race gun used in a June 28, 1947 regatta was a double-barrel 12-guage Winchester shotgun loaded with live ammunition. Thirty-two shells were fired, at least some accidentally when the safety and trigger were tripped.
    “Unquestionably, it would have been far better to use some other means of starting the races,” a “startled and shocked” Coast Guard captain wrote.
    In reply the commodore typed, “your hasty letter of the 30th of June in which I was so severely reprimanded for being careless and senseless … was considered by the undersigned as a bit strong.”
    They had seen a lot, that generation of sailors, and knew how to make do with the materials that came to hand.