Yes, you are seeing a roller skating bear!
George and Carrie Crapsey retired from entertaining and brought the bear back to Oregon. They lived at a service station at the top of the Greensprings highway outside of Ashland, Oregon securing Alice Teddy to a big tree. The bear was an attraction at the out-of-the-way service station but was sold after she took a swipe at Carrie during feeding time. She died near Portland at a unnamed wildlife place. George had trained her with sugar cubes and advised the Portland people to do the same. When the new owners whipped the bear - she struck out and that was the last anyone heard of her.
The Crapseys moved from the Greensprings to Ashland, Oregon at 29 Granite Street. Carrie died there in 1941 and George died in 1943 after having married a second time to Anna Walker, a woman whom he knew from Wisconsin. George had relatives in Oregon but they saw nothing of his money, the roller skates or fancy western clothing after he died. According to the nieces and nephews George left behind, Anna Walker Crapsey did not contact them or share any possessions or property of George's. But they had memories and good times. He was their Santa Clause at Christmas and their camping and fishing partner in the summer, 4th of July was always spent with George and Carrie. George was a violin maker and played the old time fiddle music with gusto. He loved to dance and entertain and had the vaudeville spark for the rest of his life.
The photos were in the possession of George's great niece, 92 year old Georgia Coggins in Medford, Oregon.