Partner City


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

Then and Now Photos

Ojibwa Tipis at the Forks Ojibwa Tipis at the Forks

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.

Early Winnipeg Early Winnipeg

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.

Sleighs on Main St Sleighs on Main St

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.

A Dog Sled Team A Dog Sled Team

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.

Businesses on Main Businesses on Main

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.

Bankers Row Bankers Row

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.

The Heart of Town The Heart of Town

Virtual Heritage Winnipeg 00-149 & On This Spot Enterprises

The Heart of Town - 1905

A fantastically busy day on Main and Portage.

Woman on the Corner Woman on the Corner

Virtual Heritage Winnipeg 00-159 & On This Spot Enterprises

Woman on the Corner - 1907

A woman stands on the corner of Main and Bannatyne.

Boniface Cathedral Boniface Cathedral

Virtual Heritage Winnipeg 07-122 & On This Spot Enterprises

Boniface Cathedral - 1910

The ruins of Boniface Cathedral.

Funeral at the Cathedral Funeral at the 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.

Busy Sidewalk Busy Sidewalk

Virtual Heritage Winnipeg 01-069 & On This Spot Enterprises

Busy Sidewalk - 1915

People on a busy Main Street during the First World War.

Specials on the March Specials on the March

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.

North on Main Street North on Main Street

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.

View of the Legislature View of the Legislature

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.

A View Down Portage A View Down Portage

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.

Fort Garry Gate & Hotel Fort Garry Gate & Hotel

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.

Countess of Dufferin Countess of Dufferin

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.

Fort Garry Gate & Hotel (2) Fort Garry Gate & Hotel (2)

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.

VE Day Decorations VE Day Decorations

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.