Harry is a serious, hard worker who will always get the job done, and realizes that his priorities are keeping the line in tip-top shape! He has two granddaughters: Tanya Cupper and Kara Cupper. Harry is a longtime employee of the Indian Valley Railroad, and an experienced railroader who loves to share his stories of his early days on the line. His pride and joy is his workshop which he keeps organized in his own fashion. Harry is also an inventor and is quite able to improvise repairs. He visited Shining Time Station a six years later on the occasion of his granddaughter Kara's go-kart race.