In 1924, the CNE Association hired the architectural firm of Chapman and Oxley to create a fifty-year plan for the redevelopment of the eastern end of the CNE grounds.
A significant feature of this plan was the construction of a monumental entrance to link the CNE with the city of Toronto.
This entranceway, built in 1927 on the 60th anniversary of the Confederation of Canada, was originally named "The Diamond Jubilee of Confederation Gates."
When it was learned that Prince Edward and Prince George would visit the CNE in 1927, the Gates were renamed the Princes' Gates in honour of the two royal brothers. Prince Edward, provided with gold scissors, cut the purple ribbon to officially open the Princes' Gates on August 30, 1927.
The Princes' Gates were designed in the decorative Beaux-Arts style. A Roman arch forms the centre gate and is flanked on each side by a colonnade of nine Ionic columns. The nine columns represent the participating provinces of Confederation (Newfoundland joined Confederation in 1949). At each extremity of the Gates are curved pylons with fountains at their bases.
Dominating the Princes' Gates is the Winged Victory.
Standing in a symbolic ship of state, the purpose of the Winged Victory is to guide the CNE and Canada into the future. In the lowered hand of the Winged Victory is a single maple leaf, a symbol of Canadian independence and autonomy. Some academics, including Victor E. Graham maintain that the CNE's Winged Victory figure is directly modelled on The Winged Victory of Samothrace in the Louvre, in Paris.
Flanking the Winged Victory on either side of the main arch are two pairs of identical figures. One pair of these figures hold cornucopias, representing the fruits of the harvest.
The other pair of figures hold beehives, representing hard work and prosperity. The sculptures on the pylons also possess symbolic meaning. The female figure holds a sheaf of grain to represent farming while the male figure represents industry, his left hand resting on a wheel, a set of drawings draped across his knees. Sculptor Charles D. McKenchie was responsible for all the figures adoring the Princes' Gates.
The Princes' Gates were rededicated in 1977 to mark their fiftieth anniversary. In 1987, the badly weathered Winged Victory was replaced with a state-of-the-art polymer resin replica. In 1994, the other four figures located on the main arch were also recast. In this latest attempt to restore the Princes' Gates, the new statues were recast using the same materials as the originals, poured concrete.