The airline was established in 1963 by bush pilot Otto John Hegland and started operations in July 1963 from its base at Big Trout Lake, Ontario (but was named after Bearskin Lake where Hegland had a general store). It started out by providing only charter services to the remote First Nationsreserve in northern Ontario, using bush planes equipped with floats in the summer and skis in the winter. In 1977, they began their first regular scheduled flights between Big Trout Lake and Sioux Lookout.Bearskin Airlines, Bear Country: Special 45th Anniversary Issue, 2008, ISBN D702544
From then on, other scheduled flights were progressively added, first to Thunder Bay, followed by Kenora and Winnipeg. This was also the period when the Government of Ontario began constructing new airfields that would make the northern communities accessible year-round. Therefore in the late 1970s to the early 1980s, Bearskin made the transition of bush planes to wheeled commuter plane.