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The area known as Charleswood is located in southwestern Winnipeg with the Assiniboine River forming its northern border. Its early history includes its seasonal use by First Nations bands taking advantage of the abundant fuel (wood) and food (fish, fowl and other animals) living in and along the Assiniboine River.

One of its early prominent features was geographic, the narrowing and shallowing of the river at present-day Berkley Street became an important fording location and was commonly known as "The Passage". Herds of bison and later hunters, explorers, fur traders and settlers all availed themselves of this natural ford.

Permanent settlement of the area began in the mid-19th century as retired fur traders of the Hudson's Bay Company took land and began farming. They settled on long, thin strips of land known as River Lots that ran 2 miles back from the river bank. Names of the early settlers of the region include Beauchemin, Hogue, Morrissette, and Branconnier. [1]

A ferry, an important area service, was established at The Passage in 1870 and then moved upstream in 1908 near the present-day Perimeter Bridge. It was in use until the late 1950s.

In 1880, the Rural Municipality of Assiniboia was incorporated, combining the former Parishes of Headingley, St. Charles, St. James and part of St. Boniface on both sides of the Assiniboine River. Present-day Roblin Boulevard, one of the area's main thoroughfares, was surveyed in 1899 and became an important east-west link. It was upgraded in 1908 and streetcar service was begun. In 1912, the area incorporated as the Rural Municipality of Charleswood, maintaining this political structure until it became part of the City of Winnipeg in 1972 with the creation of Unicity. Much of its eastern area left the Municipality in 1913 to form the Town of Tuxedo.

Two possible explanations exist for the origin of the name "Charleswood." It may have been named for resident Charles Kelly who served on the first municipal council or it may be a combination of the Parish name "St. Charles" and a description of the dense woods in the area.

The 1920s were a period of growth for the area, as schools, churches, stores and other services all began appearing. The Independent Order of Odd Fellows Home on Roblin Boulevard, opened in 1922 as an important area institution. But much of the area remained rural, with mud and gravel roads, limited residential development and a local economy based on agriculture- dairy and poultry farms, market gardens and mink ranches. In fact, it wasn't until the 1960s and 1970s that sustained residential construction occurred, creating new neighbourhoods such as Elmhurst, Eric Coy, Marlton and Varsity View. In spite of this growth, there are still many areas in Charleswood that have not been significantly upgraded, where the ditches and gravel roads remain.

In 1995, the twin-spanned Charleswood Bridge was opened, creating an important north-south connection over the Assiniboine River to Portage Avenue.

[1] Charleswood Historical Society.