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Adjacent to Victoria, British Columbia, and overlooking the Oak Bay Islands Ecological Reserve, this 465-acre residential community is widely considered one of the first formally planned subdivisions in Canada. It was designed between 1907 and 1908 by John Charles Olmsted for real estate developer William Gardner.

Olmsted’s curvilinear street plan departed from the grid patterns typical of Canadian subdivisions. The main artery, Midland Road, was designed as a boulevard servicing streetcars and motorcars. Olmsted prepared a detailed survey with five-foot contour intervals to ensure that the roads would work in harmony with the natural topography and that significant landscape features, including existing Garry oak trees and bay views, were preserved and protected.

Olmsted prepared innovative guidelines for protective deed restrictions to retain the carefully designed character. Before construction began, the development faced insurmountable financial difficulties and most of the land was sold in 1911, although Gardner was able to require adherence to the design when the property changed hands. The municipality of Oak Bay agreed to take over the enforcement of the restrictions. Olmsted continued to make revisions while his associate James Dawson managed details such as decorative light fixtures and grading revisions. The Uplands Tramway, in service 1913–1947 was not built in the median of Midland Road as originally planned but within the roadbed.  The boulevard design along Midland Road was never built, and recommended tree spacing conflicted with the tramway poles and wiring; those trees were not planted. The Olmsted firm ended their involvement in 1921.

In 1946 Gardner sold an undeveloped seventy-six-acre tract to the municipality for a public park. This section contained significant cultural landscape features, including Indigenous archaeological sites, plus Garry oaks, rocky crags, and panoramic ocean views. While there has been further subdivision of larger lots, the street network generally follows the original design plan of 1907. Uplands is one of two complete Olmsted-designed neighborhoods in Canada, along with Scarboro in Calgary, Alberta. On August 19, 2019, the Government of Canada designated Uplands as a National Historic Site.