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The first patent of land was issued to Ezekiel Benson, a land surveyor, on August 7, 1820. That was followed by land issued to Alan Robinet in 1822.

In 1863, Orangeville was named after Orange Lawrence, a businessman born in Connecticut in 1796 who owned several mills in the village. As a young man, he moved to Canada and settled in Halton County. During Mackenzie’s rebellion in 1837, he was a captain in the militia. Lawrence purchased the land that became Orangeville from Robert Hughson. He settled in the area in 1844 and established a mille. The post office dates from 1851.Orange Lawrence died by suicide December 15, 1861. In 1873, the Act of Incorporation was passed and Orangeville was given town status on January 1, 1874. The public library, located at Broadway and Mill Street, was completed in 1908. Andrew Carnegie, well-known businessman and philanthropist, provided financial assistance for its construction.

Orangeville serves as an administrative and commercial hub for Dufferin County, which sits to the north of the Region of Peel. Orangeville’s downtown core is home to a substantial number of retail stores, and there is a cluster of big-box stores in the Fairgrounds Shopping Centre. Many residents in and around Orangeville also commute to different areas of the Greater Toronto Area and Southwestern Ontario for work.

There are a number of manufacturing plants located in the town. Major commercial and industrial employers include: the Resolve Corporation, a provider of computer outsourcing services; Allied Threaded Products, a fastener manufacturer; Greening Donald, a maker of automotive airbag components; Clorox Company of Canada, Glad garbage bags; Relizon Canada, pressure-sensitive labels; Rochling Engineering Plastics, formerly Symplastics Limited, plastic sheets; and Sanoh Canada, automotive components. Orangeville is also the main banking centre for residents in the area.

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.