September / October 2022

The “Race of the Century”

Bugeyes on the bay test the Chesapeake’s racing spirit
Illustration of bugeyes racing.

As the gun fires, BROWN SMITH JONES leads BEE and prepares to set her spinnaker, which has been hoisted in stops. The workboats-turned-yachts were racing to win the title of fastest bugeye on the bay.

It started on an October evening in 1936, with a drink in hand, as so many of the best challenges often do. After a sumptuous dinner at the Gibson Island Clubhouse near Annapolis, Maryland, on a broad veranda overlooking Chesapeake Bay, J. Linton Rigg declared, “I’ve got the fastest bugeye on the bay.” The newest owner of the bugeye BROWN SMITH JONES had a point: she had been feared by nearly every oyster poacher on the bay 40 years earlier, when the Oyster Police used her to enforce catch limits. She had a rapid-fire rifle on her foredeck, and she could outrun any poacher she encountered.

Rigg, a yachtsman, real-estate broker, and writer, was a character right out of a Gatsby novel. Larger than life and unapologetic, his epitaph described him as a “yacht broker, designer, bon vivant and person of questionable tastes who went cruising.” Exhaling smoke from his postprandial cigar, Henry du Pont Baldwin, the chairman of the Chesapeake Bay Yacht Racing Association and owner of the bugeye BEE, growled, “Well…I don’t know about that.” Baldwin, a Gibson Island Club member, had raced BEE on the Chesapeake against far more modern racing schooners and sloops, with impressive results for a former working vessel.

Over a few more glasses and cigars it was settled: there was to be a match between BEE and the BROWN SMITH JONES. The competition would start directly in front of the clubhouse off the Mountain Point bar, at 2 p.m. October 26. The boats would sail 100 miles down to Cedar Point and back. There would be no handicaps and no holds barred, and no protest flags were to be carried. Each boat could have unlimited crew and do whatever they wanted to make their bugeye faster. To make it interesting, each crew member had to bring a quart of whiskey that would be presented to the winner.

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