The 10 prettiest streets in Toronto

Wednesday Nov 08th, 2017



Derek Flack, blogTO

Image courtesty of: Yedman

The prettiest streets in Toronto are a collection of those that have stunning architecture, unique character or a natural setting. These are all open access streets that you can walk, ride and drive on, so get out and explore if you're thinking Toronto is lacking in beauty.

Here are my picks for the prettiest streets in Toronto.

Rosedale Valley Road
Sweeping southeast across the city underneath the Bloor Viaduct and beside St. James Cemetery, this street is at its most dazzling in the fall when the tree canopy blazes with bright colours. It's a joy to drive or bike down (going up is a bit more effort when pedalling).

Palmerston Blvd.

This Annex gem is noteworthy for its huge trees, Victorian houses, and old school street lamps, which make it feel like no other street in Toronto.

Toronto streets don't get more stately than Chestnut Park. Image courtesty of: Ettml

Chestnut Park
Palmerston isn't the only street in Toronto with old-school street lamps. Chestnut Park also boasts these fixtures, along with stately houses, a meandering easterly route and cobblestone sidewalks.

Bayview Extension
Aside from the Evergreen Brick Works, there aren't any destinations on this section of Bayview, which is all the better as the eye candy is in the Don Valley, which this street snakes through.

Eclectic architecture and vibrant storefronts keep up the visual intrigue on West Queen West. Photo by Georgette.

West Queen West
Everyone's definition of "pretty" is different, but the mix of old Toronto architecture and bustling retail on Queen is a feast for the senses, especially late in the afternoon on a warm summer day.

Humberview Road
The name kind of says it all. This street winds along the Humber Valley, providing a few peeks of the river between its tree line. It's sweeping bends make it all the more visually interesting.

The hill is steep and the views are deep. Soak it all in on Brimley Road. Photo by Derek Flack.

Brimley Road / Bluffer's Park
The portion of Brimley Rd. south of Kingston Rd. is breathtaking as it sweeps down the Scarborough Bluffs. As you descend, the stunning St. Augustine's Seminary appears on the right before you're enveloped by the tree canopy. Near the bottom, the lake spreads out majestically.

May Street
This short street in Rosedale is one of the prettiest in a neighbourhood that's full of them. Extra points are earned here for the cobblestone road surface, the reserved but beautiful old homes, and the soaring trees.

King's College Circle is a sanctuary in the heart of the city. Photo by Mike Campbell.

King's College Circle
If St. George is U of T's main drag, then King's College is the university's most beautiful street, flanked by Convocation Hall and University College. From the north end of the circle, you can take in the Toronto skyline hovering over the old buildings.

Russell Hill Road
This is a pretty street in general, but the section south of St. Clair to Boulton Drive is particularly noteworthy with a sweeping curve, tall trees, and majestic homes set far back from the road.


Post a comment