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Charleswood School, 1914. Source: Len Van Roon


By Verna Van Roon


The earliest occupants of this area were First Nations.  The area showed occupation for 5000 years.  Some used the Kuyper site (approximately 1 mile west of the Perimeter) as a camping area as they waited for the Buffalo to come to the shelter of the forested area before winter.

The crossing at Berkley North was the fording place where the hunters from the forks and from St. Frances Xavier (Grant Town) crossed to go south on the buffalo hunt.  They would rendezvous at this site.  A provincial plaque now marks this crossing.  Our 1816 map shows this.


Charleswood became a separate municipality in 1913 with George Chapman as the first reeve.  We remained a separate municipality until 1971 when we became part of the City of Winnipeg. 


Charleswood was a farming district – grain, hay, cattle, mink and poultry.  It had a very small population.


The first 2 churches built in Charleswood were St. Mary’s Anglican built in 1922 and Charleswood United built in 1933.  Both congregations met in schools prior to these dates.  Roman Catholic congregations crossed over to St. Charles or went in to Winnipeg.  Their first local church was built after the Second World War.


There were 3 schools in our area: Charleswood School (behind the current day Legion), built in 1922; Chapman, built in 1913; and Loudon (currently used as the Maintenance Site) built in 1909.  Chapman and Loudon were elementary schools and Charleswood School served as the high school for 3 different school districts. 


After the Second World War, Roblin Park was established as a veterans' settlement and our population grew rapidly.  Later, Westdale and River West Park were added and many new streets.


The roads were gumbo mud, travelled mostly by horses and later a few cars.  The roads make our present day roads look pretty good.  Early in the 19th century, Charleswood was the location of “The Passage” – a natural ford at the foot of Berkley St., where the Assiniboine River was shallow enough to cross.  The Passage was frequently used by buffalo hunters travelling to Pembina, and independent traders wanting to bypass the Forks in defiance of the Hudson Bay Company’s monopoly. Around 1865, a river road was cut through the dense woodland along the south bank of the Assiniboine River, which is today’s Roblin Blvd.  A ferry was established at the Passage in  1870 linking Berkley St. with Rouge Road.  Later, the water became too shallow there and the ferry was moved to St. Charles close to the present Cass St.


The name “Charleswood” has two probable sources of origin.  One is that it was named for Charles Kelly who served on the first municipal council.  The other is that it is a combination of the Parish name “St. Charles” and the dense woodland that filled the area.

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