Barrie at its inception was a train station, which is was disconnected, but rebuilt in 2007. The city was named in 1832 after Sir Robert Barrie, who was in charge of the naval forces in Canada and frequently had to portage from Lake Simcoe to Georgian Bay through the city. The Underground Railroad in the mid 1800s caused many American slaves to enter Barrie. This contributed to the development (and the name) of nearby Shanty Bay. During World War II the Royal Canadian Navy named a Flower class corvette HMCS Barrie.
On 27 September 1977, in dense fog, a small plane hit the 68 meter tall CKVR Television Tower, knocking CHAY FM and CKVR-TV off the air. All on the aircraft were killed, and the tower was destroyed. A new 304 metre tower was erected and operational within a year.
On 31 May 1985, an F4 tornado struck Barrie, during the The "Barrie" Tornado Outbreak of 1985.
On 12 June - 13 June 1987, a sculpture called Spirit Catcher by Ron Baird was moved to Barrie from Vancouver, British Columbia, where it had been exhibited as part of Expo '86. The sculpture was erected permanently at the foot of Maple Avenue on the shore of Kempenfelt Bay.
In January 2004, Barrie made international news when its city police raided the former Molson brewery, and found Canada's largest illegal cannabis grow operation.
Barrie's Park Place (formerly Molson Park) was chosen to host Live 8 Canada on 2 July 2005. The success of the concert contributed to the resistance to a plan to convert the concert area to a commercial district.