The origins of the Kolapore Trails can be traced to a ski trip by members of the University of Toronto Outing Club (UTOC) to the McGill Outing Club’s house in the Laurentians in February 1973.   This trip introduced the UTOC members to the traditional ski trails of the Laurentians and made them aware of the fun of wilderness skiing.  Subsequent exploration around the UTOC Cabin at Metcalfe Rock revealed that the area had tremendous potential for cross-country skiing, and the idea of the Kolapore trails was born.

A federal Opportunities for Youth Grant allowed the hiring of workers during the summer of 1973, and these workers plus UTOC volunteers in the fall of 1973 created the initial trail network.  The trails officially opened in December 1973.   The first winter was a great success; members of the Outing Club fell in love with skiing in the Kolapore Uplands, and a few other skiers managed to find the trails, guided by a rudimentary map that sold for 25 cents.

After 50 years, many things have changed.  The trails are now managed for biking and hiking in addition to cross-country skiing.  Trail standards have been substantially upgraded.  The trails are managed by an incorporated organization – the Kolapore Wilderness Trails Association – and the University of Toronto Outing Club has no formal role in the trails.  The awareness and popularity of the Kolapore Uplands has increased dramatically, partly because of the trails.  Over time there has been increased recognition of the very significant natural values of the Kolapore area, and the need to protect the area.   What hasn’t changed is a desire to have a great wilderness trails system that is managed by dedicated volunteers.  

County Forest (Established 1973): For a number of years the County Forest trails were not linked to the rest of the trail system.

Jackrabbit Trail (1976): Named after the legendary Jackrabbit Johannsen, who developed many of the trails in the Laurentians that inspired the Kolapore Trails. Originally called "Scared Old Lady" after the landowner who turned down our request for permission, but subsequently renamed after our consciousness had been raised.

John's Portage (1979): Named after John Cross, one of the original Kolapore trail builders and a heritage river canoeist.

Kingsway (1989): Named after Bruce King, perennial volunteer, current President of the Kolapore Wilderness Trails Association and one of the founders of the trail network in 1973.

Kolapore Church Trail (1973/82): The route from the University of Toronto Outing Club Cabin to the Kolapore Church. For several years, this trail only went through The Gulch but a bypass was added in 1982.

Marc's Folly (1973): A group of trails named for Marc Podell, who originated the idea of the Kolapore Trails. The "folly" trail disappeared in the early years.

Mount Dhaulagiri (1973): In 1973, it seemed that every outdoor gear company was providing equipment to the American Dhaulagiri Expedition. So we thought, "Why not have a Canadian Mount Dhaulagiri?' Needless to say, no equipment was forthcoming.

New Chute (1974): Replaced the original Chute, which only a handful of skiers were crazy enough to try in the one winter it existed.

Northwest Passage (1982/87/89/93): The longest trail in the Kolapore system. Part of the "Magellan Loop" around the perimeter of the trail system.

Paradise Highway (1973/85): This trail has evolved over the years. The original version of this trail went up and down what is now Wild Mouse and also included Red Death. The "Paradise" name was used because this was the original name of Kolapore.

Quiet Pastures (1973/74)

Red Death (1973/88): The name actually refers to a winter camping drink, hot strawberry Jello.

Southern Crossing (1980): The western segment into Labyrinth used to be called Hemlock Forest.

Trail to the Summit (1973/2005): This trail was originally called Serpens. The summit referred to is, of course, Mount Dhaulagiri.

Wild Mouse (1973/74/99): This complex of trails includes parts of what used to be Ghost River and Keyhole Trails. The name refers to a favourite ride at the Canadian National Exhibition that, like the trails, provides lots of thrills. There used to be a middle run in Wild Mouse but this was removed in 1999 due to tornado damage.

And then there are the trails that have disappeared:

• Bowles Loop and Wicked Baronet - some pieces of flagging tape marked these "trails" but they never really existed.
• Great Arc, north of the Labyrinth
• Labyrinth, a tangle of trails in the southwest corner of the network. 
• Little Bear, south of County Forest
• Mad Hillbilly - a small portion of this has been incorporated into Northwest Passage.
• The Wild West and Lake Eugenia, west and south of Labyrinth

Most of the trails that no longer exist were only "sort of" developed in 1973 and disappeared in a rationalization in 1974.