Oriole was originally launched as Oriole IV in 1921 as the personal yacht of George H. Gooderham, an Ontario distiller and political figure. She was the fourth in a line of vessels named Oriole that served as the flagship to the Royal Canadian Yacht Club of Toronto, Ontario. Work was stopped on her construction due to a strike, but the vessel was taken to Neponset, Massachusetts where she was completed.
She was originally rigged as a schooner but her sail area was reduced to make her easier to handle for sail training and now she is a 102′ x 18.5′ x 9.5′ (31-metre) sailing ketch displacing approximately 100 tons and carrying 14,447 square feet of sail. Her mainmast is 87′ and her mizzen 55′ above deck. A Cummins 165 bhp diesel engine powers her when the wind isn’t strong enough to propel her. She has sleeping accommodation for 21.
During the Second World War Oriole was chartered by the Royal Canadian Navy as a training vessel. Following the war the ship was returned to the Navy League. in 1950 she was again chartered by the Navy as a new recruit-training vessel. Oriole IV subsequently moved to Halifax, Nova Scotia, in 1951 and officially commissioned HMCS Oriole 19 June 1952. Two years later the navy moved her to CFB Esquimalt to serve as a training vessel to the Naval Officer Training Centre. In 1956 she was purchased outright and attached to HMCS Venture at Esquimalt.
She is currently the oldest commissioned vessel in the Royal Canadian Navy, and also the longest-serving commissioned ship in the RCN.
The Oriole provides sail training to junior officers and non–commissioned officers. She participates in many events, races and public relation day sails. HMCS Oriole has frequently acted as the Salute Vessel for the Victoria Classic Boat Festival.