The plan for the railway was largely executed by Frederick Chase Capreol who was fired as manager of the company the day before the ground broke.
A combination of factors, including the Great Depression and the opening of a wider Welland Canal led to decreased use of the ports, and traffic fell.
With the passage of the Railway Guarantee Act in 1849, Capreol joined forces with Charles Albert Berczy and chartered the company in July 1849, now having to raise conventional bonds for the first 75 miles (121 km), from which point government funding would be available.
Continued difficulties delayed construction, during which time the company re-chartered as the Ontario, Simcoe and Huron Union Railroad in 1850.
[4] Early construction required the line to pass over the Oak Ridges Moraine, and it was not until 16 May 1853 that the first train reached Machell's Corners, today's Aurora, Ontario.
Cumberland focused on profitability, cutting any train that didn't pay for itself, strongly resisting any expansion plans, and selling off their small fleet of ships operating on the Great Lakes.
This resistance to expansion would ultimately backfire; in 1864 the company was approached by businessmen from Grey and Bruce counties about building a line through their burgeoning agricultural areas.
This left an opening for the formation of the Toronto, Grey and Bruce Railway (TG&B), which began construction toward Owen Sound in the spring of 1869.
Faced with their first real competition, the Northern chartered their own North Grey Railway on 15 February 1871, with plans to extend out of Collingwood to Meaford and authority to continue to Owen Sound.
Construction between Collingwood and Meaford took place over the flat terrain between the Niagara Escarpment and the southern shore of Georgian Bay, and the line was completed on 1 April 1872.
Upset with the Northern remained, and demand for additional shipping routes on the Lakes led to intense building through the entire area.
The H&NW finally agreed to run a branch line to Collingwood, splitting off the mainline some distance west of Newmarket, and added optional plans for an extension north from Barrie to Midland.
This provided the funding and income needed to begin construction of the Northern and Pacific Junction Railway, which ran between Gravenhurst and Nipissing.
CNR operated the mainline as the CN Newmarket Subdivision, selling off the branches to the west, and pulling up the section between Barrie and Orillia.
The first locomotive of the Ontario, Simcoe and Huron Union Railroad was named Lady Elgin and built in Portland, Maine.
[17] The OS&HR was recognized for its contribution to railroading as a "Community, Business, Government or Organization" in the "National" category (pertaining specifically to the area in and around St. Thomas, Ontario.)