|First Appearance||Rickety's Ridiculous Ruckus (Cameo)|
|Basis||Type 4B two seat Wickham Trolley|
|Livery||Red with gray lining|
|Voice Actor|| CA62Mini
Winston came to the railway after Sir Topham Hatt's car broke down. He was used as his car for a while, until Sir Tophm Hatt's car was repaired. However, Winston was still used by Sir Topham Hatt to shuttle him around the railway even after the car was repaired, due to how reliable he was. Even nowadays, Sir Topham Hatt uses Winston around the Island, and some say that he is even used more than Sir Topham Hatt's car. He was recently upgraded so that he can now go on both road and rail.
Winston is a thoughtful, loyal, willing, helpful track inspection vehicle. He is very patient with Sir Topham Hatt's, frankly, terrible driving skills and enjoys his company. Winston loves the chance to explore and find out things for himself whenever he can, and is very adventurous.