During this period, his business interests extended into the Red River Colony, which he was committed to developing. In 1856, he opened a store at St. Boniface (now modern Winnipeg, Manitoba) and the following year he and other merchants shipped over $120,000 of furs from the Red River Settlement to St Paul. Although he sold the store in 1861, Kittson continued to import furs from the settlement and provide it with supplies. He was a long-time operator of Red River cart brigades on the Red River Trails, which served his trading businesses.
