A poem published by John H. Hardie in 1671 described Bermuda's boats in the following way: "With tripple corner'd Sayls they always float, About the Islands, in the world there are, None in all points that may with them compare".
With the buildup of the Royal Naval Dockyard on Ireland Island, at the West End, and of the Army garrison, at first in the East End, at St. George's Garrison,[2] though the military headquarters eventually moved to Prospect Camp at the centre of the colony, the idle navy and army officers, most ex-Public School boys, introduced a number of team sports to the colony.
The rough, wind-driven Atlantic Ocean proved unsuitable, however, and the officers soon took to employing the local work boats for sail racing.
By 1880 there was great concern that the need for professional crews in sloop racing was making the sport too expensive, and that its development was stagnating, as a direct result.
In 1883, Princess Louise, daughter of Queen Victoria, visited Bermuda, and she donated a trophy which was awarded to the winner of a dinghy race held on 8 March, which was restricted to boats both owned and steered by club members.
Original Bermuda Dinghies were roundbottomed and fitted with long, shallow keels so they would be easy to beach or could run over reefs without damage.
During the first recorded race, held in St. George's Harbour in 1853, the existing boats were fitted with deep keel extensions fastened in place temporarily to give them the bite to sail better to windward.
Although it is true that mounting a dinghy campaign requires significant financial and personnel resource, new entries are welcomed regardless of race, and many of Bermuda's best-known fitted sailors are black, including Stevie Dickinson and Glenn Astwood.
The racing is carried out on set dates in a variety of locations including Hamilton or St. George's Harbours, Granaway Deep, and Mangrove Bay.
The dinghies sail windward leeward courses and the number of legs is decided based on the conditions at race time.
The boats, despite their small sizes, are each normally crewed by six people, necessary to handle the large areas of sail, and also to continually bail the dinghies, which have very little freeboard, and which are often capsized by powerful gusts.