In the fall of 1944, Henry G. Glyde and fellow artist A.Y. Jackson hoped to return to the Yukon to continue to document activities in that region for the National Gallery of Canada. However, they decided to visit Rosebud, Alberta instead because of the difficulties of arranging transportation with the Royal Canadian Air Force. Jackson had passed through this small town many years before, and had hoped to return. Along with Glyde, he stayed in a local hotel, where they were welcomed by the community. They spent two sunny, warm weeks wandering the hills, sketching, and painting farms and ranches.

In 1947, three years after his visit with Jackson, Glyde used one of his sketches to paint Rosebud, Alberta, the same year that he became head of the Department of Fine Arts at the University of Alberta.