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.
Historic Walking Tours
Bullseye of the Dominion
The Boomtown Era 1870-1912
The Challenge of Modernity
Turmoil and Reform 1913-1945
Then and Now Photos
Virtual Heritage Winnipeg 06-113 & On This Spot Enterprises
Ojibwa Tipis at the Forks - 1858
Ojibwa people have erected their tipis at the Forks, a type of housing perfectly suited to the harsh conditions of the prairies.
Virtual Heritage Winnipeg 00-078 & On This Spot Enterprises
Early Winnipeg - 1870
A view of how the "mushroom patch" of early Winnipeg, located at Main and Portage, looked like from Fort Garry.
Virtual Heritage Winnipeg 00-101 & On This Spot Enterprises
Sleighs on Main St - 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.
Wikimedia Commons & On This Spot Enterprises
A Dog Sled Team - 1900
A man poses with his dog team and sled by the old gate of Fort Garry. The sled is labeled Norway.
Virtual Heritage Winnipeg 00-135 & On This Spot Enterprises
Businesses on Main - 1903
A view of the west side of Main. Only a handful of buildings survive.
Virtual Heritage Winnipeg 00-140 & On This Spot Enterprises
Bankers Row - 1905
Looking south on Main Street towards some of the banks that gave the strip its moniker.
Winnipeg Archives CA COWA C13-P00006-97 & On This Spot Enterprises
The YMCA - 1905
A postcard view of the YMCA Building on Portage Ave.
Virtual Heritage Winnipeg 00-149 & On This Spot Enterprises
The Heart of Town - 1905
A fantastically busy day on Main and Portage.
Virtual Heritage Winnipeg 00-159 & On This Spot Enterprises
Woman on the Corner - 1907
A woman stands on the corner of Main and Bannatyne.
Virtual Heritage Winnipeg 07-122 & On This Spot Enterprises
Boniface Cathedral - 1910
The ruins of Boniface Cathedral.
Virtual Heritage Winnipeg 07-083 & On This Spot Enterprises
Funeral at the Cathedral - 1915
A funeral procession for Archbishop Louis Phillippe Adelard Langevine leaves St. Boniface Cathedral.
Virtual Heritage Winnipeg 01-069 & On This Spot Enterprises
Busy Sidewalk - 1915
People on a busy Main Street during the First World War.
Winnipeg Archives CA COWA C13-P00001-22 & On This Spot Enterprises
Specials on the March - 1919
A large group of 'specials' march down Portage Ave during the General Strike of 1919.
Virtual Heritage Winnipeg 01-076 & On This Spot Enterprises
North on Main Street - 1928
A streetcar trundles past the Union Bank Tower, seen at left. The tower is the oldest surviving skyscraper in Canada.
Virtual Heritage Winnipeg 02-223 & On This Spot Enterprises
View of the Legislature - 1928
Looking past the new Hudson's Bay department store down Memorial Boulevard towards the Legislature.
Virtual Heritage Winnipeg 02-386 & On This Spot Enterprises
A View Down Portage - 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.
Virtual Heritage Winnipeg 04-268 & On This Spot Enterprises
Fort Garry Gate & Hotel - 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.
Winnipeg Archives CA COWA C13-P00023-83-13 & On This Spot Enterprises
Countess of Dufferin - 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.
Winnipeg Archives CA COWA C13-P00002-46 & On This Spot Enterprises
Fort Garry Gate & Hotel (2) - 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.
Winnipeg Archives CA COWA C13-P00015-79 & On This Spot Enterprises
VE Day Decorations - 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.
