There's something about the Toronto skyline that maintains allure even as it risks becoming a cliche thanks to the thousands of times it's photographed each day. Never is this feeling more palpable than when you stumble upon a hidden vantage point that few before you have enjoyed. Bring a love interest. These are great spots to explore together.

Here are 5 secret spots to view the Toronto skyline.

Kensington Market parking garage

It doesn't look like much from street level, but climb to the top of this parking garage on St. Andrew St. at dusk and you'll be treated with one of the best views of Toronto you'll ever witness. Unlike lakeside vantage points, this view shows off Toronto's dense urbanity.

The skyline hovers over Crothers Woods. Photo by Derek Flack.

Crothers Woods

One of the most truly hidden spots on this list, you'll need to hike about 200 metres from the upper trailhead (at the Loblaws parking lot) to the top of the hill that local mountain bikers once dubbed K2. Curl around the trail for different skyline angles of the CN Tower and Financial District, which hover over the lush Sun Valley.

The view of Toronto above Davenport Rd. is magnificent. Photo by Derek Flack.

Regal Road School

Perched atop the old Lake Iroquois shoreline, this lookout offers a stunning panoramic view of Toronto. You'll need to walk up the mostly hidden path from Davenport Rd. to avoid being encumbered by the fence, but once you've found it, you'll surely go back again. It's that good.

This parkette is a great place for a picnic or a game of chess. Photo by Tony Mo.

Miles Road End Parkette

A number of south Etobicoke streets terminate at little lakeside parkettes, but the one at Miles Rd. is my favourite. There are two benches and a chess table (which also works for a picnic) here, meaning it's a comfortable spot to lounge for an hour or two with the city shimmering in the distance.

A trip to the Chester Hill Lookout is required for any Torontophile. Photo by Evan Russell.

Chester Hill Lookout

Chester Hill isn't as well kept a secret as it once was, but if you pay a visit, you're still unlikely to encounter others doing the same. Tucked north of Broadview and Danforth, this lookout offers a view of Toronto that's at once natural and profoundly urban, where the Bloor Viaduct serves as a visual dividing line between the valley below and the skyline.