The idea for creating the Bruce Trail came about in 1959 out of a meeting between Ray Lowes and Robert Bateman, of the Federation of Ontario Naturalists.

On September 23, 1960, the first meeting of the Bruce Trail Committee took place, consisting of four attending members—Ray Lowes, Philip Gosling, Norman Pearson, and Dr. Robert McLaren.

With a team of volunteers, he visited major towns along the proposed route to discuss their vision of the trail and to solicit help from landowners.

The cairn at the northern terminus of the Bruce Trail in Tobermory was unveiled in 1967 to coincide with Canada's Centennial Year.

[5] In August 2021, the Bruce Trail Conservancy purchased nearly 400 acres of land known as the Maple Cross Nature Reserve, its largest acquisition to date.

There is also a wide range of plant and wildlife along the trail, including slow-growing centuries-old coniferous trees right on the limestone lip of the escarpment itself.

The Bruce Trail and the escarpment run through some of the most populated areas of Ontario, with an estimated 7 million people living within 100 km (62 mi).

It continues due north through the major towns or cities of Hamilton, Burlington, Milton, Halton Hills, Walters Falls, Owen Sound, Wiarton, and finally Tobermory.

The Highlands Trailblazers Nordic Ski Team completed a relay-style run of the entire trail in 8 days, starting in Tobermory on June 24, 2008, and finishing in Queenston on July 1, 2008.

[19] In 2009, two 10-person teams running continuously in an event called the Blaze Race set a new end-to-end relay record of 3 days, 23 hours, and 10 minutes.

[20] In 2012, adventure seekers Fred Losani, Peter Turkstra, Mark Maclennan, and Teemu Lakkasuo went on a quest to raise funds and awareness for inner-city food and nutrition programs in Hamilton, as well as the Bruce Trail Conservancy as they celebrate 50 years.