Sackville Street begins at a chain-link dead end, and it’s downhill from there. All of Cabbagetown’s northern edge is pressed up against St. James Cemetery, one of the city’s finest. Sackville is a little stub of road that extends north of Wellesley for a hundred metres or so, and begins a consistent line of Victorian pleasantness running south, made so by pioneering gentrifiers — so-called "white painters" — in the early 1970s.
Sackville does run noticeably downhill. On a bike you can coast all the way to Gerrard if you are liberal in your interpretation of what a stop sign means. On foot, the grade results in effortless walking. It feels strange to write this, but one of the nicest things about Sackville, and Cabbagetown in general, are the fences. These aren’t the 6-foot-high suburban fences I grew up with, but proper, low, wrought-iron fences with squeaky gates that close with a bang and rattle. They mark the divide between public and private in the gentlest way, inviting and allowing the exchange of pleasantries between residents and those passing by. Watching it happen on warm spring days it seems that this is as it should be, everywhere.
From spring until late summer, the southern Sackville entrance to Cabbagetown at Gerrard is a fertile gauntlet provided by rival corner stores that display an explosion of portable foliage that Cabbagefolk pick up in their red wagons. To the south is Regent Park, and this is where you'll find what is perhaps the most abrupt and dramatic social and economic shift in Toronto. It's an experience almost like being in Detroit, where, along Mack Avenue, the ruins of the modern American wasteland bump up against the ultra-rich and manicured Grosse Point.
But unlike Mack Avenue, Gerrard stops being a mental barrier after a few visits. On the Regent Park side, there are usually kids shuffling about with a ball of some kind, teenagers voguing like they’re in a 1970s Springsteen song and people taking groceries out of 1989 Honda Accords — the same stuff that happens in the rest of the city.
Though the area was completely redeveloped in 1948, and the southern part of Cabbagetown — "the largest Anglo-Saxon slum in North America" — was razed, you can still follow the ghost of Sackville Street as you head south. Midway through Regent Park, on what was once Oak Street — made famous by the 1953 NFB film Farewell to Oak Street — a spectacular temporary view of Toronto’s skyline comes into view. The southwest quadrant of Regent Park has been torn down, and until the new buildings rise, we’re afforded this unique view of the city. At Dundas Street is St. Cyril and Methody, a Macedonian-Bulgarian church where, if you pass through on a Saturday night, you can look into the basement hall and see and listen to West Indian wedding receptions taking place under florescent tube lighting.
Just south of Dundas, the former Sackville roadway is filled in with grass and blocked by a large iron fence, but the sidewalks are still exactly where they would be if the street were intact. To the south, by the Regent Park Community Centre, it’s harder to follow Sackville’s ghost, as a wading pool, some elaborate concrete ramps, and a neglected, paved-over tree pit were installed over time. This is called "Sackville Green," so the name lives on, and includes a sign stating that this is an alcohol-free zone, and comes complete with a crossed-out picture of a martini with an olive on a toothpick.
Towards Shuter Street, Sackville regains its form and passes though Trefann Court, an area that was supposed to be redeveloped in the 1960s but was halted by a historic community effort to keep the small neighourhood intact. On Queen Street’s south side is St. Paul’s Catholic School with a schoolyard full of hundreds of buried Irish refugees who fled the 1847 Great Hunger.
Here, Sackville faces its greatest hurdle — the twin elevated roadways of Richmond and Adelaide. Directly in front is the green, impenetrable berm the roadway is built on. Sackville doesn’t end here, though; it curves to the east and at what appears to be another end, there is a secret passageway that feels illicit but allows pedestrians to pass through to King Street via a parking lot under the highway.
The lot skirts the side of the Riverside Missionary Church, best known for its "Prepare to meet they God" sign, which the drivers on Richmond Street pass. Just east on King is the Sackville Playground. There is no sign of the street in the park. It was created when Richmond and Adelaide became super-arterial roads in the 1960s, a sort of mini-Spadina-expressway, removing existing streets and buildings, creating this new space.
There is a crosswalk on King here that leads to that last bit of Sackville that extends one block down to Eastern, where it finally comes to an end. Remarkably, and with the exception of the traffic light at Gerrard, the pedestrian has the right of way the entire length of Sackville from the cemetery to Eastern Avenue, through either stop signs or push-button crosswalks. Even though it’s been chopped up, blocked, and rerouted, Sackville Street still lives on foot.