For those who live in the downtown core or West Toronto, the Rosedale Valley feels like a kind of eastern boundary in the city – one of the last roads to the east before reaching the Don Valley Parkway (DVP). But the East Toronto neighbourhoods lie beyond the DVP boundary, making the Rosedale Valley an accessible connector between the downtown core and the Don Valley trail system and neighbourhoods beyond. It is also a main feature of the Toronto Marathon’s route for both the 21.1 km and 42.2 km races each spring.

The Rosedale Valley Trail proper is 2.5 km long but connects to a wide variety of other trail systems and routes in the city, allowing you to create a longer run if you wish. These can be accessed from the top (northern part of the valley at Yonge and Aylmer) or the bottom (the southern part at Rosedale Valley Road and Bayview Avenue) of the Rosedale Valley. If you start at the northern part, you can access the valley road just south of the TTC Rosedale station on Yonge Street. Here you will find Aylmer Road, a short connecting ramp which curves southeast to join Rosedale Valley Road. While running down Aylmer, stay on the sidewalk on the north and east side of the road. As Aylmer and Rosedale merge, cross over to the west side where you will notice a paved but worn trail that runs parallel to Rosedale Valley Road. Follow this trail and you will find yourself running downhill into a tree-shaded valley that is particularly breathtaking in the fall, when the leaves change colour and the valley turns gold, orange, and red. Look up and you will notice that you pass under a number of large bridges as you run – these are some of Toronto’s major east-west roads which cross the valley as they connect the centre of the city with eastern neighbourhoods such as Greektown, Leslieville, and Riverside.

As you near the bottom of the valley trail you will notice a grassy cemetery to your right; this is St. James’ Cemetery and Crematorium, which, having opened in July 1844, is Toronto’s oldest operating cemetery. Shortly after passing the cemetery, you will see Bayview Avenue appear ahead and, on your right, a paved trail leading into a small parkette. This marks the end of the Rosedale Valley Trail, and the start of the “choose your own adventure” part of the run: if you continue to Bayview Avenue, you can join the Don Valley trail system, run up to the scenic grounds of Brickworks, or from there take Milkman’s Lane back up to the residential streets of Rosedale. However, if you turn right into the little park in the valley, the trail will lead you to a long staircase that will bring you up to Wellesley Park. From there, you can head west on Wellesley to get back into the city centre, or go south on Sumach Street to Riverdale Park West, where the infamous Riverdale hill can add a little extra workout to your run. Or, of course, you don’t have to leave the valley at all – you can simply turn right around and run back up the valley for a 2.5 km climb to Yonge Street!