[8] The airline was established in 1963 by bush pilot Otto John Hegland and began operations in July 1963[2] from its base at Big Trout Lake, home of the Kitchenuhmaykoosib Inninuwug First Nation.

It started by providing only charter services to the remote First Nations reserves in northern Ontario, using bush planes equipped with floats in the summer and skis in the winter.

This was also the period when the Government of Ontario began constructing new airfields that would make the northern communities accessible year-round.

Following the collapse of NorOntair in 1996, Bearskin picked up over two-thirds of that carrier's routes, thereby adding scheduled service to all the major northern Ontario cities including Marathon, Timmins and Wawa.

In July 2003, it sold its routes and assets servicing northern First Nations communities to Wasaya Airways for $18 million.

It participated in the Aeroplan rewards program until June 30, 2018 (the airline merged with Perimeter Aviation on December 31, 2017).

Since then, Bearskin Airlines is part of Perimeter Aviation's frequent flyer program, Connecting Rewards.