If you've ever attended Exhibition Place in Toronto, you've likely walked under the Princes' Gates numerous times without knowing its history.
The 350-foot-long triumphal arch at the foot of Strachan Avenue serves as the iconic eastern gateway to Exhibition Place, and while it's now a familiar sign that you've finally made it to the Canadian National Exhibition (CNE), the monument's history stretches back nearly a century and reflects both the growth of the exhibition and Toronto itself.
The CNE itself was established all the way back in 1879 at the foot of Dufferin Street. As the exhibition grew, it gradually expanded eastward, and by the 1920s, planners were considering a grand entrance at Strachan Avenue.

Concrete details of the eastern entrance to Exhibition Place. Photo: City of Toronto Archives.
In the mid-1920s, the CNE Association tasked Toronto-based architects Chapman and Oxley — the same firm behind local landmarks such as the Royal Ontario Museum — with drafting a 50-year plan for the revitalization of the exhibition's grounds.
A key fixture of this plan was the introduction of a monumental entrance at the easternmost point of the grounds to serve as a gateway between Exhibition Place and the city.
Construction of the arches took place between April and August 1927 at a cost of roughly $152,240 (which adjusts to approximately $2.78 million in 2025 after inflation).

The Princes' Gates in 1927. Photo: City of Toronto Archives.
The result was a grand entranceway built in time for the 60th anniversary of Canadian Confederation, originally called "The Diamond Jubilee of Confederation Gates."
However, upon news that Edward, Prince of Wales, and Prince George were visiting Exhibition Place, the gates were renamed "Princes' Gates" in honour of the two royal brothers.

The monument's ribbon-cutting ceremony in 1927. Photo: City of Toronto Archives.
During their visit, Prince Edward (later crowned King Edward VIII in 1936) was presented with gold scissors and used them to cut the purple ribbon, officially opening the Princes' Gates on Aug. 30, 1927.
The monument was designed in the same decorative Beaux-Arts style as other landmarks of the era, like Union Station. Its central arch, evoking the triumphal arches of ancient Rome, is flanked by rows of nine Ionic columns, each vertical pier representing one of the provinces in the Canadian Confederation at that time.

Princes' Gates in 1936. Photo: City of Toronto Archives.
The intricately designed monument includes fountains at its base on either side, as well as its most recognizable feature, the Winged Victory, an ancient Greek figure perched atop the central arch. Despite its Aegean roots, if you look closely, you'll notice that the figure is holding onto a maple leaf in its left hand, meant to symbolize Canadian independence.
You'll also find two sets of identical sculptures on either side of the main arch, with one pair holding onto cornucopias (fruits of harvest), and the other set grasping beehives, which were intended to represent hard work and prosperity.

The monument in 1939. Photo: City of Toronto Archives.
Many relevant themes of the annual exhibition were incorporated into the monument, including one figure that holds a stack of grain for farming, while another one holds onto a wheel and drapes a series of drawings across his knees to signify industry. All of the figures adorning the Princes' Gates were created by sculptor Charles D. McKechnie.
However, the weather took its toll on the monument over the years, and the Winged Victory was replaced with a polymer resin replica in 1987. Additionally, four other figures located on the main arch were recast using poured concrete in 1994.

Princes' Gates, sometime between 1984 and 1990. Photo: City of Toronto Archives.
In 2007, the main arch was revitalized as part of a project that grew upon the relationship between Toronto and its sister city, Milan. The project included a revitalization of the Piazza Princes' Gates, which introduced new pedestrian and cycling amenities as well as improved landscaping.

Princes' Gates in 2005. Photo: City of Toronto Archives.
In 2010, the monument and other buildings at Exhibition Place underwent further restorations as part of a $27.3 million initiative.
And, now, in 2025, almost a full century after the gates were built, the landmark is one of a handful set to be spruced up with new lighting upgrades ahead of the 2026 FIFA World Cup games scheduled to take place in Toronto next year.

Princes' Gates in 2019. Photo: Jack Landau.
Although there's a decent chance you pass by the Princes' Gates regularly, gaining a deeper understanding of its history can help you appreciate both the monument and the evolution of Exhibition Place.
This article has been updated after an earlier version contained an inaccuracy.
City of Toronto Archives