The Fleetwing was built in 1863 in Wilson Harbor by Alexander McNutt for John V. Pease, Benjamin Dearborn, and Orrin Quick, and was registered in Brighton, Ontario, at 89 feet by 19 feet and roughly 20 tons. In 1864, with Quick as captain, she capsized off Wilson Harbor on an early voyage, killing Quick's wife, daughter, and the ship's cook. The vessel was righted, enlarged to 110 feet by 24 feet, and registered at roughly 200 tons. Under a new captain, Malcolm Shaw, she continued carrying coal, lumber, and grains to ports along the Great Lakes, and in 1891 she also hauled crib stone for the new Eastern Gap in Toronto Harbor. After many years of service and additional accidents, Fleetwing finally ended her career in 1906, when, with much water in her hold and a very frightened green crew, she sunk near Port Milford, Ontario.