Kittson received a grammar school education at Sorel, and like everyone in his family he was perfectly bilingual. His step-grandfather Alexander Henry and four of his five paternal uncles had all been active in the
fur trade, particularly the
North West Company. It therefore was no surprise that, seeking adventure, in 1830 he took an apprenticeship with the
American Fur Company at
Michilimackinac, where Alexander Henry and many others from Sorel had been active. Kittson served at various posts in what became
Minnesota Territory in the United States. Kittson left the American Fur Company in 1833 to become a clerk to the
sutler at
Fort Snelling. In 1839, he went into business for himself, setting up as a
fur trader and supply merchant at Cold Lake, near Fort Snelling.
Henry Hastings Sibley, Kittson's old friend from the American Fur Company had risen to managing agent of the
AFC, but left in 1843 to form a partnership with Kittson. Kittson collected furs from
James Sinclair and established strong connections to the local
French Canadians. Through his first wife, he became particularly attached to the
Métis people, employing them as tripmen and trading extensively with them. All of this enabled him to play a significant part in bringing about free trade to the settlement in 1849.
Guillaume Sayer was trading with Kittson prior to the trial that ended the monopoly. In 1852, Kittson relocated from Pembina to
St. Joseph to avoid the periodic flooding of the
Red River of the North. ==St. Paul, Minnesota==