Its sidewalks are narrow, uneven, cracked and interrupted by posts. The road is as pitted as the surface of the moon.
After years of planning, preparation has begun on an extreme makeover of John St between Front St W and Stephanie St, just south of the Art Gallery of Ontario.
The vision is for a more beautiful, accessible pedestrian friendly "cultural corridor".
Sidewalks and boulevards will be widened and re-paved, more trees will be planted and public art added. The transformation will also reduce John St to a single lane of traffic in each direction between Wellington St and Stephanie St.
The hope is the eventual design will make John St more attractive a more attractive venue for cultural events and street festivals.
City of Toronto
The project, which has been in development for a decade, is not expected to be competed until the summer of 2023.
Last month, hydro crews loaded in supplies for underground work on John St, north of Queen St W. Over the next two years construction will move south, with work targeted along between Queen St W and King St W in 2019 and from King St W to Front St W in 2020.
City of Toronto
Janice Solomon, Executive Director of the Entertainment District BIA says while the process has taken longer than anyone anticipated, business owners have very much been part of the process.
"We recognize that the street has some complexities to it," Solomon tells NEWSTALK 1010. There's underground parking garage entrances, lots of little nooks and crannies and individual stakeholder needs that required addressing in the design of the street."
Solomon says the BIA will work closely with businesses to make sure there is always a way to access them during construction and signal that they are open.
People who regularly walk along John St welcome the planned changes.
Sipping a coffee outside Dark Horse near Richmond St W, Daniel calls the street derelict.
"It doesn't really reflect well in an area that's the entertainment district and is a gateway from the (Rogers Centre) up to the AGO."
Sandy says as development in the city's core has boomed, John St's sidewalks have become more crammed.
"It's competitive walking almost."
While she looks forward to a more laid back pedestrian experience, she has doubts.
"It's always in the future. And then when the future comes, who knows what the government's going to do, who knows what the funding's going to be like, who knows what the population is going to be like."