Yacht racing in Canada grew significantly in the later half of the 19th century. Chester Race Week in Nova Scotia was an annual event since 1856. The Royal Canadian Yacht Club, founded in 1852, has 4 trophies that date between 1872 and 1887. The massive silver Canada’s Cup trophy, named after the first yacht to win it, RCYC’s Canada, was first awarded in 1896 and has become the most prestigious sailing trophy on the Great Lakes.
In 1888, the Georgian Bay Yacht Club of Collingwood organized a sailing race. The Georgian Bay Cup was awarded to James Playfair as the winner of this race contested by rival sailors from Midland and Collingwood. The ”yachts” used for this race were Watts Skiffs. These were working boats of the day whose regular service was to harvest food from the bay to feed the local population.
The Georgian Bay Yacht Club ceased to exist with changes in the economy and the Georgian Bay Cup was lost. Fortunately the original Cup was found in the possession of a collector in the United States. A number of members of the Collingwood Yacht Club recovered and refurbished this relic. The Cup is being offered as the annual prize for the winner of the Georgian Bay Cup Race.