Chester Hill Lookout — Attraction in Toronto

Chester Hill Lookout Toronto’s Secret Window to the Skyline

Tucked quietly at the end of a residential street, Chester Hill Lookout feels like a hidden balcony overlooking Toronto. I arrived just before sunset and was greeted with a sweeping panorama: the CN Tower standing proud, the downtown skyline glowing gold, and the Don Valley stretching out beneath the Prince Edward Viaduct.

What I loved most was the sense of discovery, there’s no big sign or fancy entrance, just a short stroll from Broadview Avenue that suddenly opens to a remarkable view. It’s a favourite among photographers for good reason; the city lights at dusk are stunning, and autumn leaves add a rich frame around the scene.

The space itself is small and simple, with no washrooms or benches, so come prepared if you plan to linger. Traffic from the Don Valley Parkway hums below, but it’s easy to tune out while you watch the skyline. As the sky deepened, a few locals stopped by with cameras and coffees, lending the spot a friendly, relaxed vibe.

Chester Hill Lookout won’t keep you busy for hours, but for a quick escape or a romantic pause, it’s perfect. If you’re exploring Toronto or live nearby, don’t miss this charming perch, just remember to respect the neighbourhood and leave no trace.

City needs to trim down trees to unblocked the view from...

This is apparently the best view you can get of Toronto. The drive to here from Mississauga is really fun but long. It takes about 40 minutes. However, you are mostly on the highway and one of the best parts is going directly through downtown Toronto on the highway in order to get to here. You also go through a really cool bridge that lights up in blue at night in Don Valley. The lookout is in a residential area, so there is a house right next to it that probably has an amazing view of Toronto. The lookout point looks small, but you don’t need much space. You also can’t really spend more than 10 minutes here as you only see Toronto from quite a great distance. It is beautiful, however. I have gone to this location about 5 times to show my friends and family and they all think it was cool. Whenever I have gone there have been a couple of other people there as well. From the lookout you can clearly see the CN Tower and the ICE towers, but I personally cannot identify any other buildings. Driving in Toronto is a nightmare, but also fun, but if you do decide to go...

Lookout is beautiful besides the tree in the way of the city. But the neighbours are very rude. The one neighbour on the left of the lookout point has cameras that are recording and stands at the window and creeply looks out at people. I went with my boyfriend for a cute spot to take pictures, and as a short girl the huge tree in the way blocked the view. So being a normal person I step up on the ledge to get a clearer view just to have some old man who lives in the house to the left, knock on the window and point downwards telling me to get down. Who does this man think he is. I am allowed to make my own decisions and the lookout point that I was on was public property. The neighbours could be nicer to the public but if they don’t like people coming along near their...