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.
Despite his initial reluctance to accept this new post, Harry quickly grew fond of the station's homeliness and old-fashioned setting, thinking that there was "just something" about Shining Time Station. Though coming across a gruff, humorless and grumpy man to those who don't know him, Harry has a heart of gold, and never holds a grudge - even against Schemer when he tried to take over Harry's workshop. When he yells at someone, it is only his intention to keep them safe. After just working at Shining Time Station for just over a year, he was transferred to Fort Farley, and was replaced by Billy Twofeathers. Harry's last job was at Twiddly Junction where he retired.
He visited Shining Time Station six years later on the occasion of his granddaughter Kara's go-kart race.
- Season 1 - A Place Unlike Any Other, Does It Bite?, And the Band Played Off, Pitching In and Helping Out, Show and Yell, Faith, Hope and Anxiety, Agree to Disagree, Whistle While You Work, Two Old Hands, Happy Accidents, Ring in the Old, Impractical Jokes, Finders Keepers, Just Wild About Harry's Workshop, Promises, Promises, Word's Out, Too Many Cooks, Mapping it Out, Things that Go Ga-Hooga in the Night, Is This the End? and 'Tis A Gift (mentioned)
- Season 2 - Scare Dares (mentioned) and Crackpot (mentioned)
- Season 3 - Billy Saves the Day (mentioned) and Stacy Says No (mentioned)
- The Family Specials - One of the Family
- Mr. Conductor's Thomas Tales - Wish You Were Here (mentioned)