The Chester Hill Lookout

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 T.R.C.A. (Toronto Regional Conservation Authority), but leased by the City of Toronto.

The Lookout, with exceptional views of downtown, the Bloor Viaduct Bridge and Brickworks to the west, has become a magnet for people exploring the City thanks to the City’s Discovery Walks and promotion. Popularity also brings negative issues including speeding, drug use and dealing, impaired driving, garbage, vandalism, late night noise/partying and parking violations. Enforcement has been too little, too late. We have asked for changes for years.


A 1 meter wide water pipe flows beneath Chester Hill Road. Water coming from Lake Ontario is treated at the R.C Harris Treatment plant which then flows below Scarborough streets to East York and over to Chester Hill Road. This is drinking water for the downtown Toronto core. It’s piped below Chester Hill westbound then down the DVP slope and across/under

Spring 2019: A Petition was circulated to the closest residents on Chester Hill Rd and Thorncliffe Ave to request the Lookout become a Pedestrian only area (with the exception of 3 residential driveways and City service access). A group of neighbours near the Lookout have spent time and effort to compile evidence, contact 311 and Police, and communicate with Councillors Fragadakis and Fletcher on all of these issues.

Tuesday November 12, 2019 A meeting was held with Councillor Paula Fletcher, Toronto Transportation Services and Toronto Police to present the Pedestrian only Petition for the Lookout - with discussion to outline all Lookout issues. Detailed photographs of key problems were shared and the discussion was productive. A request for large, on-street planters was made for an interim solution to Lookout access by car traffic. Councillor Fletcher agreed to pursue a redesign of the Lookout. It was estimated it could take up to 2 years. Neighbours closest to the Lookout were asked to email with descriptions of negative activity (with photographs where possible) to create a history for the Councillor/City. Calls to 911 were now permitted. Until this point, neighbours had been emailing Police/calling Police non emergency.

December 3, 2012, 2019 At Toronto East York Community Council, Councillor Fletcher moved the motion below to formalize the request for design changes at the Chester Hill Lookout.

2019.Te11.63 – Chester Hill Road and Lookout- design Improvements

The request was fully approved.

Since Nov 12, we have asked for the on-street planters to be delivered asap. We have offered to bring them to the site at our own expense.


December 12, 2019 The shooting at the Lookout occurred at 9:30pm. Please contact Toronto Police if you have any information.


Each Spring on the City’s Community Clean-up Day, neighbours come together to clean the Lookout and slopes “over the edge”. Despite the cold many residents help. We have special considerations because of the negative impact at the Lookout. The slopes “over the edge” are first surveyed and cleaned for drug waste before we allow anyone to start cleaning up.

This past Spring our clean up was an extremely cold Saturday morning. We carefully sorted garbage and recycling and had 25 bags plus picked up by the City.

Monday December 16, 2019 Planters Councillor Paula Fletcher's office coordinated the delivery of six(6) giant planters for traffic calming at the Chester Hill Lookout. Neighbours who live within the Lookout area, as well as, City Services (Garbage, Fire, Hydro, Snow) have ample room to manoeuvre. The planters are phase one of a redesign for the Lookout. A City garbage can is in the works as well. : ) These Planters are a test and are NOT permanent. We need to slow traffic in and out of the Lookout and why not make them festive and functional!

Feel free to contact Lisa Cruikshanks if you would like to volunteer to help with improvements to the neighbourhood!