This week’s Throwback Thursday, is going WAY back to when there was a bridge crossing the Don River, roughly parallel to where Winchester Street is now. If you travel to the eastern end of Winchester St. today (past the entrance to the Necropolis and Riverdale Farm), you’ll see a gate and remnants of where the road used to head down towards the river.
Originally, there was just a tree and logs tied together over the river back when the Simcoe’s lived in town, but there were upgrades along the way.
Eventually other bridges such as those at Gerrard St. East and Bloor St. meant it wasn’t necessary any longer.
For an excellent history of the bridges over the Don River from Bloor St. south, this article on blogTO is definitely worth reading.
A brief history of crossing the Don River (blogto.com)