Category: Skyline

blogTO calls the Chester Hill Lookout “Toronto’s secret observation deck” and, after visiting the location, I would have to agree with them.

Sitting at the end of a quiet residential road off Broadview Avenue, the Lookout is a semi-circular concrete observation deck jutting out at the end of a cul-de-sac on Chester Hill Road:

The Lookout offers a view that spans west across the city, with the Don Valley and the whizzing of cars on the highway below, Evergreen Brick Works sit beyond the trees to the right and the towering financial buildings to the left.

Finding the Lookout

From the Danforth, walking a few minutes north on Broadview Avenue will bring you to Chester Hill Road:

Chester Hill Road is a very quiet, upscale neighbourhood with some beautiful homes:

At the end of the block you will encounter a cul-de-sac:

Painted on the pavement of the roundabout is an astrology wheel. This chalk-work is by local artist Victor Fraser, a sidewalk artist and poet based in Toronto. He has been painting paved surfaces for the past 20 years, and has painted in six different countries. The wheel was repainted in October 2022.

Stepping to the edge of the roundabout yields an incredible urban view:

The Chester Hill Lookout was built in the late 1950’s for the construction of the Don Valley Parkway. Chester Hill Road was shortened to create the Lookout and the hillside down to the DVP. The land over the edge of the Lookout down to the DVP is owned by the Toronto Regional Conservation Authority, but leased by the City of Toronto.

Residents of Chester Hill Road report a downside to the location, though. There have been many negative issues occurring lately including speeding, drug use and dealing, impaired driving, garbage, vandalism, late night noise/partying and parking violations.

On a happier note, while the Lookout is beautiful at any time of the day, sunset and nighttime offer the most spectacular experiences. As the sun sets, the sky takes on hues of orange and purple with the city’s lights twinkling below. At night, the Luminous Veil of the Prince Edward Viaduct adds a purple touch to the view. I’m planning a revisit to the site next spring to capture some of this.