Partner City
Winnipeg
Chicago of the North
Winnipeg grew up around the gathering place at the Forks between the Red and Assiniboine Rivers. When Manitoba joined Confederation in 1870 it sparked a tremendous population boom that lasted until the early 20th Century and made Winnipeg the first city of the Canadian prairies. Winnipeg is a city with an exciting history of rebellion, reform, commerce, and culture. The city is host to dozens of fascinating historic buildings.
These photos and tours are possible through the generous support of our partners.
Virtual Tours
Walking Tours
Explore Spots in Winnipeg
Then and Now Photos
Ojibwa Tipis at the Forks
Virtual Heritage Winnipeg 06-113 On This Spot Enterprises
1858
Ojibwa people have erected their tipis at the Forks, a type of housing perfectly suited to the harsh conditions of the prairies.
Early Winnipeg
Virtual Heritage Winnipeg 00-078 On This Spot Enterprises
1870
A view of how the "mushroom patch" of early Winnipeg, located at Main and Portage, looked like from Fort Garry.
Sleighs on Main St
Virtual Heritage Winnipeg 00-101 On This Spot Enterprises
1882
People mill about in a snow-covered Main Street during the winter of 1882. The City Hall at the end of the block, which doubled as a 250-seat theatre, would soon be demolished and replaced by the impressive 'gingerbread' City Hall.
A Dog Sled Team
Wikimedia Commons On This Spot Enterprises
1900
A man poses with his dog team and sled by the old gate of Fort Garry. The sled is labeled Norway.
Businesses on Main
Virtual Heritage Winnipeg 00-135 On This Spot Enterprises
1903
A view of the west side of Main. Only a handful of buildings survive.
Bankers Row
Virtual Heritage Winnipeg 00-140 On This Spot Enterprises
1905
Looking south on Main Street towards some of the banks that gave the strip its moniker.
The YMCA
Winnipeg Archives CA COWA C13-P00006-97 On This Spot Enterprises
1905
A postcard view of the YMCA Building on Portage Ave.
The Heart of Town
Virtual Heritage Winnipeg 00-149 On This Spot Enterprises
1905
A fantastically busy day on Main and Portage.
Woman on the Corner
Virtual Heritage Winnipeg 00-159 On This Spot Enterprises
1907
A woman stands on the corner of Main and Bannatyne.
Boniface Cathedral
Virtual Heritage Winnipeg 07-122 On This Spot Enterprises
1910
The ruins of Boniface Cathedral.
Funeral at the Cathedral
Virtual Heritage Winnipeg 07-083 On This Spot Enterprises
1915
A funeral procession for Archbishop Louis Phillippe Adelard Langevine leaves St. Boniface Cathedral.
Busy Sidewalk
Virtual Heritage Winnipeg 01-069 On This Spot Enterprises
1915
People on a busy Main Street during the First World War.
Specials on the March
Winnipeg Archives CA COWA C13-P00001-22 On This Spot Enterprises
1919
A large group of 'specials' march down Portage Ave during the General Strike of 1919.
North on Main Street
Virtual Heritage Winnipeg 01-076 On This Spot Enterprises
1928
A streetcar trundles past the Union Bank Tower, seen at left. The tower is the oldest surviving skyscraper in Canada.
View of the Legislature
Virtual Heritage Winnipeg 02-223 On This Spot Enterprises
1928
Looking past the new Hudson's Bay department store down Memorial Boulevard towards the Legislature.
A View Down Portage
Virtual Heritage Winnipeg 02-386 On This Spot Enterprises
1920s
Looking east on Portage Ave towards Main Street from Carlton during the roaring '20s. Winnipeg's commercial centre of gravity was shifting to this area from Main Street at the time.
Fort Garry Gate & Hotel
Virtual Heritage Winnipeg 04-268 On This Spot Enterprises
1930
The Fort Garry Hotel looming over the old gate of Fort Garry. The fort itself was dismantled in the 1880s and only the gate remains.
Countess of Dufferin
Winnipeg Archives CA COWA C13-P00023-83-13 On This Spot Enterprises
1930s
The first locomotive to arrive in Winnipeg in 1878, the Countess of Dufferin, has been preserved and put on display outside the CPR station.
Fort Garry Gate & Hotel (2)
Winnipeg Archives CA COWA C13-P00002-46 On This Spot Enterprises
1930s
The Fort Garry Hotel looming over the old gate of Fort Garry. The fort itself was dismantled in the 1880s and only the gate remains.
VE Day Decorations
Winnipeg Archives CA COWA C13-P00015-79 On This Spot Enterprises
1945
The Eaton's store on Portage has been decked out with flags and bunting to celebrate the end of World War II in Europe.