To honour the traditional Bermuda Day fitted dinghy regatta, we have compiled vintage photos that reveal the few changes that have been made to the boat from then to now. This year’s Bermuda Day races which kick off the season will take place on Sunday afternoon, May 28th, in St. Georges. The teams will be vying for the annual Heritage Trophy, the Anniversary Cup and the Leon D. Fox Cup.

Dinghy races in St. George’s harbour in the 1950’s
Three Bermuda fitted dinghies going windward with the spectator fleet in the background. Note the leg-of-mutton mainsails harking back to the 1800s and the origins of the Bermuda Rig.
Bermuda fitted dinghies waiting for the start before hauling themselves up a rope laid along both side of the stake boat at set intervals depending upon their rating.
Opening of the fitted dinghy racing season at St. George’s.
Jubilee Cup Winner: “Elizabeth” (at left), skippered by Nat Butterfield, flows past “Venture” during the first spinnaker run in the Jubilee Cup race. “Elizabeth” also won the Coronation Cup.
Crew members dive off stern to give extra push and lighten dinghy as wind abates near finish line.
The fitted dinghy Contest racing under full sail.
Julia, Oscelola, Electra racing in Hamilton Harbour 1870s