The Toronto Belt Line Railway
The Toronto Belt Line Railway was a passenger service that was proposed, privately built, and failed in the 1890s – The route was intended “to service and promote new suburban neighbourhoods north of the city limits through the communities that eventually became Rosedale, Moore Park, Forest Hill and Swansea - The line was never profitable and it only ran for two years - Today, as part of a rails-to-trail project, the remaining part of the line is now the Beltline Trail” – Wikipedia – It was an idea that was over 125 years ahead of it’s time
"The railway consisted of two separate loops both starting and ending at Union Station. The larger loop went east to the Don River. It turned north following the river before journeying up a steep grade through the Moore Park Ravine beside the Don Valley Brick Works. It then turned west at the north edge of the Mount Pleasant Cemetery along Merton St. At Yonge Street it turned northwest travelling through Forest Hill until just north of Eglinton Avenue West. There, it turned west again before returning to Union Station via the Canadian Northern Railway (now CNR) line west of Caledonia Road. A complete trip was approximately 40 km (25 mi).
A second, smaller loop headed west along the northwest rail corridor. It turned west just north of St. Clair Avenue and then turned south at Lambton Mills, just east of the Humber River. It ran south following the edge of the Humber River valley. It followed a route paralleled by the South Kingsway just west of High Park. It returned east along Lake Ontario." - Wikepedia