Discover Chester Hill Lookout in Toronto
Toronto has a lot to offer, it's filled with city parks, cultural landmarks, other unique things to do, and some of the best urban adventures around, like a CityDays Treasure Hunt for example! Among these great attractions, Chester Hill Lookout is a real hidden gem. Situated in the east end of Toronto, in a quiet residential neighbourhood off Broadview Avenue, this lookout spot provides sweeping, panoramic views that span west across the city. Visitors can take in the lush landscapes of the Don Valley and the Prince Edward Viaduct, against the urban backdrop of the iconic CN Tower, and the city's financial district.
Beyond its incredible views, on the semi-circular concrete observation deck, visitors will find a large astrology wheel, a piece of geometrical street art created by Toronto’s renowned sidewalk artist known as @whatsvictorupto. The artwork, with its almost spiritual quality, draws many curious visitors to Chester Hill Lookout. The secluded nature of the spot, which has a kind of small-town hilltop car park vibe that turns golden with the setting sun, also draws couples looking for a romantic date idea in Toronto.
Creating the Chester Hill Lookout
Chester Hill Lookout is located in the Rosedale neighbourhood, one of Toronto’s most historic and affluent areas. Originally, this area was part of the traditional lands of the Mississaugas of the Credit River. As Toronto grew and expanded, the lookout became a beloved spot for residents to enjoy the natural beauty and skyline of their city.
The lookout itself was constructed in the late 1950s during the development of the Don Valley Parkway (DVP). To accommodate this project, Chester Hill Road was shortened, creating the lookout and the hillside leading down to the DVP. The land extending from the lookout to the DVP is owned by the Toronto Regional Conservation Authority (TRCA) but is leased by the City of Toronto.
Increasing Popularity of the Chester Hill Lookout
Thanks to the City’s Discovery Walks program, Chester Hill Lookout gained popularity for its exceptional views of downtown Toronto, the Bloor Viaduct Bridge, and the Evergreen Brick Works. However, with its rise in popularity came negative consequences such as speeding, drug use, impaired driving, littering, vandalism, and late-night disturbances. Local residents have expressed concerns about these issues for years, calling for better enforcement and changes to the area.
Addressing Community Concerns at Chester Hill Lookout
In Spring 2019, a petition was circulated among residents of Chester Hill Road and Thorncliffe Avenue to request that the Chester Hill Lookout be designated as a pedestrian-only area, apart from residential access and city services. The community requested large, on-street planters until a solution was granted to restrict car access to the lookout. During a hearing, where the petition was submitted to the City, councilors agreed to pursue a redesign, estimating it would take up to two years.
Community Clean-Up Initiatives
Every spring, during the City’s Community Clean-Up Day, local residents gather to clean the Chester Hill Lookout and the slopes leading down to the DVP. This event is particularly important due to the negative activities that occur at the lookout. The area is first surveyed and cleared of drug-related waste before volunteers begin the clean-up. Despite challenging weather conditions, the community's efforts result in a cleaner and safer environment for all.
Features of the Chester Hill Lookout
Evolution of the View
While the lookout spot has been popular for a while, it's the view that has changed over the years. In July 2015, this spot overlooked under-construction projects like the L Tower, Sun Life Financial Tower, Harbor Plaza Residences, and Bay Adelaide Centre’s east tower. Fast forward to October 2019, and the skyline has been significantly altered with new additions such as CIBC SQUARE, Dundas Square Gardens, and Massey Tower.
Water Supply
A unique feature of Chester Hill Road is the one-meter wide water pipe running beneath it, delivering treated water from Lake Ontario. The water is processed at the R.C. Harris Treatment Plant and flows beneath Scarborough streets to East York and Chester Hill Road. From there, it continues westbound down the DVP slope, supplying drinking water to downtown Toronto.
When is the Best Time to Visit the Chester Hill Lookout?
While the lookout is beautiful at any time of 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 beginning to twinkle below. At night, the Luminous Veil of the Prince Edward Viaduct adds a magical purple touch to the view. This historical truss bridge connects the Danforth to downtown Toronto and is especially captivating when illuminated against the dark sky.
Visiting the Chester Hill Lookout
Getting There
Reaching Chester Hill Lookout is convenient whether you’re walking, taking public transport, or driving. It’s just a ten-minute walk north from Broadview Station, and even quicker by bus. However, many visitors prefer to drive, as it offers the flexibility to linger and enjoy the view from the comfort of their car. This spot is particularly favored for its intimate and private atmosphere, making it a popular date night destination.
Chester Hill Lookout isn’t just for couples seeking a romantic spot. It’s also a favorite for photographers aiming to capture Toronto’s skyline, especially during the golden hours of sunrise and sunset. Nature lovers will appreciate the lush greenery of the Don Valley, while art lovers can admire the striking blue and gold geometric print on the lookout’s floor.
Tips for Visiting
- Respect the Space: Chester Hill Lookout is cherished by its locals. Be mindful of noise levels and dispose of any litter properly to maintain the area’s cleanliness.
- Safety First: The lookout is on a hill with some uneven terrain. Be cautious, especially if visiting after dark, and keep an eye on children and pets.
- Bring Essentials: Depending on the season, bring essentials such as water, sunscreen, or warm clothing. Toronto’s weather can be unpredictable, so it’s best to be prepared.
Things to Do at Chester Hill Lookout
While the primary draw of Chester Hill Lookout is its view, there are several activities and attractions nearby that visitors can enjoy:
- Bring a Picnic: With its peaceful atmosphere, Chester Hill Lookout is an ideal spot for a picnic.
- Nature Walks: The surrounding Rosedale neighbourhood and nearby parks, such as Riverdale Park and the Don Valley, offer numerous trails for walking and exploring nature.
- Historical Exploration: Rosedale is known for its historic homes and architecture. Take a stroll through the neighbourhood to admire the well-preserved houses and learn about the area’s history.
- Explore beyond the lookout: Nearby attractions include the Todmorren Mills or the Evergreen Brickworks.
Visiting Toronto with CityDays
If you’re interested in exploring hidden gems like Chester Hill Lookout we think you will enjoy one of our CityDays Treasure Hunt in Toronto and in particular, the Old Town Hunt.
Our urban adventures bring the secrets of Toronto to life in a fun and interactive way, so you can uncover the history of the city whilst exploring its often overlooked places of interest such as historic marketplaces and an intriguing fountain.
Along the way, you and your teammates will solve puzzles and clues that interact with the streets themselves to unlock fascinating facts as well as uncover great cafes, pubs, and plenty of surprises.
The Old Town Hunt is an ideal trail for locals, visitors and anyone looking to make the most of this unique and fascinating area. We think you’ll love it but for more information on this tour, and our other Toronto adventures click here: Toronto Urban Adventures | CityDays.
