In 1841 James Sinclair, a University of Edinburgh educated leader of the Red River Metis, led a party of emigrants from the Red River Colony in present day Manitoba to Oregon. The journey was instigated by George Simpson, governor of the Hudson Bay Company, in order to reinforce the British and Hudson Bay Company's presence in the area.

The party was made up of 23 Metis families totalling 121 people, including a 75 year old man and babies born during the trip. They travelled first to Fort Edmonton and then proceeded south to enter the mountains at Devil's Gap. They travelled along the south side of Lake Minnewanka, over a pass between Mount Peechee and Princess Margaret Mountain and then down Carrot Creek to the Bow Valley. After travelling a few kilometres down the Bow Valley they abandoned their Red River Carts and ascended to White Man Gap between Ha Ling Peak and Mount Rundle, travelled up the Spray valley to White Man Pass, descended the Cross River to the Kootenay River from which they crossed Sinclair Pass (below Mount Sinclair) to the Columbia and eventually reached Oregon.

In 1854, Sinclair guided by the Cree chiefMaskepetoon who claimed to have knowledge of a shorter route, led a second party to Oregon from Red River, this time a group of about one hundred driving 250 head of cattle. After receiving reports of a shorter route, they travelled up the Kananaskis River and are thought to have crossed North Kananaskis Pass, a remarkable accomplishment although te route turned out to be much lengthier than that followed in 1841.

Sadly, James Sinclair was shot and killed in 1856 when Indians attacked an American post on the Columbia River that he happened to be visiting.