In 1907, the Franco-Canadian Trust Company and its subsidiary, Uplands Ltd., began development of 465 acres, formerly the Hudson’s Bay Company Uplands Farm established in 1851. The company engaged John Olmstead of Olmstead Brothers - foremost North American landscape architects - who designed New York’s Central Park and Mount Royal Park in Montreal, to design the subdivision. Francis Mawson Rattenbury as company architect, was responsible for building design approval.

The gates were commissioned in 1912 and designed by architects Jennings and Boulanger as part of a promotional plan, in conjunction with the Uplands development. Their intent was not one of protection – as we see in today’s gated communities – but rather to signify the status of properties within the gates. John Olmstead disapproved of their construction, believing them meaningless, given that eight roads lead into the Uplands.

The three sets of gates are unique in design and purpose. Each set of gates is different, while having certain design features and proportions in common. The original architectural plans called for posts to be made of concrete, with iron connecting pieces and bronze plaques. However, the south-east gates at Beach and Thorpe place are constructed of granite block, linked to smaller posts by a curved iron fence: the south-west gates at Uplands and Cadboro Bay Road are concrete panels, of similar design and proportion: the north Beach Drive set, similar in design to the concrete south–west gates, but without the secondary posts and iron connections.

The Uplands Gates are a significant landmark within Oak Bay, defining the properties known as “The Uplands” and providing a sense of status to the community. The gates are on their original sites and are structurally sound. The eastern pillar at the North Gates received substantial damage from an automobile accident, but was recently restored by Stewart Monumental, using the original Jennings and Boulanger design.