Sport and recreation has been a fixture on the Charlottetown waterfront since the early part of the 19th century. The Charlottetown Regatta, held from the 1820s up to the 20th century featured rowing, sailing and swimming events, often with teams from visiting British and foreign naval vessels. Before the First World War motorboating was added to the roster of events drawing on the popularity of gasoline engines, may of which were manufactured by Bruce Stewart in his factory at the foot of Great George Street.
The Hillsborough Boating Club, which was the home to many rowers and scullers in the Harbour was also a popular swimming and diving location. It was founded before 1890 and its clubhouse on the Prince Street Ferry Wharf was a landmark until the 1920s. The HBC Cup was one of the many trophies for which sailboats competed. There was also an organization called the Charlottetown Aquatic Club prior to WW I which seems to have organized motor boat competitions.
The Charlottetown Yacht Club was first organized in 1922 and the next year saw the creation of a fleet of eleven small boats which competed avidly for many years. The club was re-organized in 1936 and incorporated the following year. This led to the building of a clubhouse and other facilities at the foot of Pownal Street where the club continues to be the home of an active sailing community.
While winter halted most harbour activities iceboating was a popular pursuit and continues to this day when ice conditions allow.