Owen Sound was originally known as Sydenham when it was first settled in 1841 by Charles Rankin. It gained its current name in 1851 and was incorporated in 1857.
Originally a port city, its status has declined with the opening of the St. Lawrence Seaway. Farming in the local area and tourism are now integral parts of the local economy.
Owen Sound is the hometown of the World War I flying ace Billy Bishop and the local airport (Billy Bishop Regional Airport) is named after him. His boyhood home is now a museum dedicated to his life and to Canada's aviation history.
The town was also the home of the artist Tom Thomson a member of the Group of Seven.
According to the 2001 Statistics Canada Census:
| North: Owen Sound | ||
| West: Georgian Bluffs |
Owen Sound | East: Meaford |
| South: Georgian Bluffs |