The main intersection in the heart of the town is Broadway (formerly
Highway 9) and First Street.
Highway 10 runs through Orangeville on its east side. Beginning in 2005, a major roadwork project was initiated to resurface Broadway through Orangeville. The downtown section was completed in early 2006, with extensive work still to be done on the west end in late 2006. In conjunction with this project, there was another one completed in late 2006 that involved building large planters in the middle of Broadway through the downtown section between First and Third Streets (West - East). The project was controversial, as safety concerns had been raised by the fire department because the new concrete planters in the middle of the road have made the rights of way too narrow for fire trucks to properly set up in case of a fire in a downtown building. A section of County Road 109, often referred to as the "Orangeville bypass", is a
bypass opened in 2005, running east–west connecting Highway 10 with a pre-existing section of County Road 109 that was formerly Highway 9 running west out of town. Much of the eastern stretch runs through the Town of
Caledon, but officially enters Orangeville at the Townline Road intersection, where it is named Riddell Road.
Orangeville Transit is the town's public transit system, and there is a commuter
GO Transit bus service to
Brampton. In 2023, Orangeville Transit introduced a two-year pilot program of
free public transport under which no fares were collected on any of its routes within the town. In 2024 the town announced the pilot program would continue until at least 2027. Orangeville became the largest town or city in Canada with free public transport. In the early 1990s, preliminary plans were drawn up for GO Transit passenger rail service to Orangeville. However, it never got past the drawing board. Industries in Orangeville were served by the
Orangeville Brampton Railway, which purchased of surplus track from the
Canadian Pacific Railway. The railway connected with the CPR in
Mississauga, and also serviced customers in Brampton to the south. From 2004 to 2018, a tourist train was operated on weekends in summer months. The last train out of Orangeville was December 17, 2021. In 1906, survey work was underway for an electric railway line which would serve Orangeville, to be called the Huron and Ontario Electric Railway. The planned line would have connected Orangeville with
Goderich, Ontario. The line was proposed during a period where
electric railways was popular in Ontario but many would end up in the hands of
Ontario Hydro in the 1930s or fail. Like the 1902
Ontario West Shore Railway this line was never built. ==Education==