Stephen is one of the earliest engines ever built. Newer engines may be faster and stronger than Stephen, but what he lacks in terms of strength or speed, he makes up for with his positive spirit, sense of humour, and knowledge. He used to work at docks and in mines, but now works as a tour-guide at Ulfstead Castle. He can often be seen pulling an open-topped carriage and was trapped in the Ulfstead Mine where he discovered King Godred's long lost crown in time for the opening of the castle. In the seventeenth season, he gave Percy a lucky horseshoe when he was having bad luck, helped him trick James and took the Afternoon Tea Express.
Stephen is a jolly old engine with a positive attitude and a good sense of humour. He is a good-hearted and quick-witted engine, and will not take any nonsense from engines like Spencer or Diesel. Some of the smaller engines look up to him for advice, and he is always willing to get the job done.
- 1800's Colt Gatling Gun
- Knight's sword
- Knight's battle ax
- Musket rifle
- Stephen will meet Winnie the Pooh, Ash Ketchum, Littlefoot, Simba, SpongeBob, Mickey Mouse, Tai, Princess Twilight Sparkle and their friends in Pooh's Adventures of Thomas & Friends: King of the Railway. In this movie, Piglet, Spike the Dragon, Apple Bloom, Sweetie Belle, Scootaloo, Heckle, Jeckle, Pikachu, Togepi, Timon, Pumbaa, Zazu, SpongeBob, Patrick, Littlefoot, Cera, Ducky, Petrie, Spike, Chomper, Ruby, Guido, Puffin, Speed, Jean-Bob, Abu and Iago all joined him starting at the Steamworks on his quest to find his new job, get trapped in the mine with him and finding King Godred's crown; and in the end, Stephen calls them his new best friends.
- Tigger refers to him as "Stephen boy", which he likes that nickname a lot.
- Stephen will make his first guest starring appearance in Thomas' Adventures series in Thomas the Tank Engine Gets Frozen.
- Stephen will make his first guest starring appearance in Pooh's Adventures Series in .
- Stephen is also the Rocket's brother.
- Stephen is also best friends with Filthy Rich.
- Stephen, along with Melody and Vanellope von Schweetz, became a new member and helper of the Cutie Mark Crusaders. He is also one of the two mentors of the Cutie Mark Crusaders (the second mentor is Hiro).
- Stephen will guest star Thomas and Twilight Sparkle visit Jurassic Park and great trapped in the park with Dr. Grant, the CMC, Spike, Lex, Tim, Willy, Mako, The Miner trains, and Shai-Shay and appear in Thomas and Twilight Sparkle visit The Lost World: Jurassic Park and Thomas and Twilight Sparkle visit Jurassic Park III.