Part of a series on my favourite walking trails in Toronto.

Hey Toronto, remember to practice Physical Distancing during the COVID-19 pandemic! As part of its COVID-19 strategy, the City of Toronto has closed the parks noted below. The Trail itself is open for walking, but the parks and their facilities are not.

And now on to the regular post …..

Toronto, like any city, has many neighbourhoods and all of them have some history and uniqueness to them. Some are hip and trendy, some are gritty, and some are upscale and stately. Rosedale is the latter. It’s long been known as a district of fine older homes set amongst quiet leafy streets, and that makes it a great area for a summer’s shady walk. Here’s a route that I’ve done before, and it’s equally great in the spring and autumn too.

Length: around 8 km, so about 1.5 hrs

Surface: paved (except in the parks)

Public Transit: To start, take the subway Line 1 to St. Clair Station. The finish on the route map is at Line 1 Rosedale Station, but an alternative is to finish at Line 1 Summerhill Station, both on Yonge Street.

Route:

Starting at St. Clair Station, exit the subway onto St. Clair Avenue East. Walk east on St. Clair (on the south side of the road to Inglewood Drive. Turn south and follow Inglewood as it bends to the east. Cross Mount Pleasant Road at the traffic lights and continue east on Inglewood to its end, where it bends to the right (south) and becomes Rosedale Heights Drive. Follow Rosedale Heights south and back west until you come to MacLennan Avenue. Turn left (south) and walk down the hill to the ramp on your right leading upwards – follow that onto the pedestrian bridge over the train tracks, over, and down the ramp onto Summerhill Avenue.

Once you are over the tracks, walk east on Summerhill to Chorley Park (a great spot for a picnic). Wander through the park and exit on the south west corner onto Roxborough Drive. Follow Roxborough west, passing Rosedale United Church and Whitney Park onto Edgar Avenue. Follow Edgar west to Rosedale Park, and turn left (south) onto MacLennnan. Follow that south to the roundabout and take the road to the south-east, Highland Avenue. Follow that southeast to Glen Road. Turn right on Glen Road and cross the bridge over the ravine.

At South Drive, turn right (east) and follow that to Elm Avenue. Turn right (east) and follow Elm until it turns into Castlefrank Road. Follow Castlefrank east and then south as it bends. At Dale Avenue turn right (west) and follow Dale west to Glen Road. At Glen, turn right (north) and follow it to Maple Avenue, turning left (west) onto Maple and continuing to Sherbourne Street. At Sherbourne, turn right (north) and follow it to South Drive. Turn right (east) on South Drive and follow the curve around to the north, where it turns into Crescent Drive. Keep following Crescent as it curves around to the west and crosses over Mount Pleasant Road. To finish, follow Crescent west to to Rosedale Station, on Yonge Street.

Sights:

What’s lovely about this walk is that you get a combination of stately homes and parks for a rest. It’s a people-watching walk too, as there are always pedestrians out for a stroll. And it can be a fun, spot-the-flash-car walk as well – you’ll run out of fingers and toes before you run out of Porches to count, for example.

Rosedale prides itself on what it thinks of as understated elegance. This is not a bling-house neighbourhood, it’s more old money than new, more Chanel than Versace, more Mercedes than Ferrari. You walk here because it’s fun to imagine the lives behind the curtains.

While there’s no truly dramatic scenery nor any particularly impressive architecture, streets filled with large, red-brick homes dating back to the late 1800s tell a story of solidity and comfort. There is history here, in that the red bricks of the oldest homes probably came from the Don Valley Brickworks, like many of the other famous buildings in Toronto – Old City Hall, Massey Hall, and so on. And the area dates from a time when Canada and Toronto was establishing itself, post-1867 Confederation, as a prosperous, industrious part of the Empire.

While today, Toronto likes to think of itself as hip and is proud of natives like Drake promoting the 6, Rosedale still has a whiff of the Toronto-the-Good era, the so-called blue-light Toronto when nothing opened on Sundays, temperance movements tried to suppress the evils of alcohol, and good citizens meant good Protestants attending church on Sundays. Back then, non-WASPs had their own neighbourhoods, and Rosedale was a solidly white upper-class enclave. It’s more diverse today, but its still upper-class – the area is the wealthiest part of Toronto.

That wealth is visible in the homes, the cars, the land, and quiet streets. It’s also visible in the shops along Yonge, between Rosedale and Summerhill subway stations. There was a time when a strange face wandering through Rosedale would draw attention. Today, it’s less hide-bound, less class-ridden, and less uptight. But there’s a reason that one of the first LGBTQ bookstores in Toronto was called This Ain’t the Rosedale Library.

Food & Refreshment:

Food and refreshments on this walk are mostly around the start and finish – there are many cafes, coffee houses, restaurants, and food shops along Yonge near St. Clair, Rosedale, or Summerhill stations. In the heart of Rosedale, on Summerhill Avenue just over the train tracks, there is the Summerhill Market, Rosedale’s version of a corner store (and a fab gourmet stop on it’s own). All this gives many options to load up for a picnic, and Chorley Park is the perfect spot for that.

There are water fountains at Chorley and Rosedale Parks, available between about May-October, and there are public toilets at Rosedale Park as well. There are also public washrooms at St. Clair in the shopping mall at the north end of the station. Finally, there are washrooms, a great cafe, and water at the Brickworks if you divert from this walk (see below).

Diversions:

1. An alternative route is to turn north once you cross Mount Pleasant Road on Crescent Road, onto Wrentham Place. Follow that north to Roxborough Street and turn left (west), then north on Chestnut Park. Wind through these little streets and find Cluny Drive, turn north, and find Rowanwood Ave. Follow that around to the east onto Thornwood and then north and around to Pricefield Road. Take Pricefield west all the way past the Pricefield Playground and into Scrivener Square by the old Summerhill train station that is now the Summerhill LCBO at Yonge Street. Turn right and walk under the train tracks to Summerhill Avenue to the Summerhill Station on Line 1. This diversion takes you through more quiet, charming back streets and lets you end by the gourmet shops at Scrivener Square.
2. Another fun diversion is to cut through Chorley Park and join the connector trail that descends into the Moore Park Ravine – this will put you opposite the Don Valley Brickworks, and you can pop in there for a potty stop or food/water/coffee. The Chorley Park connector trail also puts you onto the Beltline Trail, and you can follow that south and around past the Brickworks. The Beltline continues north up through David Balfour Park, under St. Clair Avenue, and on into Mount Pleasant Cemetery to finish near Davisville Station on Line 1 subway. Or you can climb out of the trail just before you get to St. Clair, and walk back along that road to finish back at St. Clair Station.
3. You can also take the Chorley Park connector, follow the Beltline around, and then take Milkman’s Lane to climb out of the Yellow Creek Ravine and into Rosedale. This will put you onto South Drive by Glen Road, where you can rejoin the main route described above.