Thomas was working with Annie and Clarabel when, whilst waiting at a red signal, they heard a strange honking noise - it turned out to be Winston, who was new to the railway. After much going about to and fro, Winston managed to stop to allow Sir Topham Hatt to tell Thomas that he was to work at the Blue Mountain Quarry whilst Paxton was under repair. A few days later, Winston came to the Blue Mountain Quarry with Sir Topham Hatt and Mr. Percival with a message for Thomas that Paxton's repairs were completed. Later on the following day, Winston saw the Fat Controller taking no interest in Diesel's suggestions about Luke. However, he brought him and Mr. Percival to the Blue Mountain Quarry, having being informed by a very worried and confused Paxton.
After hearing Edward (Peter Pan) and Salty talk about how the Fat Controller used to travel in an open-topped carriage on his birthday, Winston was determined to find it. Winston was working with Thomas that day and he took the opportunity to look for the coach. After leaving Thomas to look for the carriage twice, Thomas made Winston travel in front of him. This ended in an accident when Thomas does not notice that Winston had slowed down. Thomas then asks Winston what he was looking for and the track inspection vehicle tells him. There, on an old siding, is the carriage. The two then bring the coach to the Sodor Steamworks to be mended and later surprise the Fat Controller with it.
Later, some tracks needed repairs, so Winston took the Fat Controller every day to check on the repairs. After Gordon and Henry laughed at him, Winston got tired of having a bad driver and decided to not remind the Fat Controller to put on the brakes. He had a near-collision with Paxton and Bertie before he ran out of fuel, just before a collision with some trucks. The Fat Controller was cross, but Winston told him that he forgot to put on the brakes. The Fat Controller realised this, and forgave Winston for his adventure. Winston knew he needed a driver after all.
One Christmas, the Fat Controller dressed up as Father Christmas for the celebrations at Ulfstead Castle. The Earl wanted him to drive a sleigh, despite the Fat Controller's views to the contrary. To get out of it, he took Winston to the Steamworks, and Winston was dressed up like a sleigh, which he did not like at all! However, much to Winston's relief, the Earl did not approve, so Winston was spared the embarrassment.
Winston is often seen when The Fat Controller comes to see his engines where there is no road nearby.
Winston is Sir Topham Hatt's track inspection vehicle. Winston is as devotedly thoughtful and loyal as a butler. He is willing, helpful, and very patient with Sir Topham Hatt's, frankly, terrible driving skills, often reminding him that it is still "early days" whenever something goes wrong. Winston helps the Fat Controller navigate about the railway without inconveniencing any of the engines while they are going about their work. Being a car on rails, he may look unconventional, but Winston is highly tolerant, considerate, patient, sensitive to others, and is only too happy to do what he can for Sir Topham Hatt, though he can, at times, become rather distracted.
Winston is a Type 4B two seat Wickham Trolley.
Winston is painted red. He has a gold nameplate on either side.
- Season 16 - Happy Birthday Sir!
- Season 17 - Wayward Winston, The Thomas Way (cameo), Percy's Lucky Day (cameo), Bill or Ben? (cameo), and Santa's Little Engine
- Season 18 - Samson at Your Service (cameo)
- Season 19 - Henry Spots Trouble and Slow Stephen (cameo)
- 2013 - Happy Birthday, Sir! and Wayward Winston
- 2014 - Happy Birthday, Sir!, Bill or Ben (does not speak), and Edward the Helpful Engine (does not speak)
- Matt Wilkinson (UK/US; sixteenth season onwards)
- Joshy Peters (Germany)
- Jarosław Boberek (Poland; sixteenth season onwards)
- Wataru Hatano (Japan; sixteenth season onwards)
- Helge Winther Larsen (Norway; sixteenth and seventeenth season only)
- Per Skjøldsvik (Norway; Blue Mountain Mystery onwards, excluding the seventeenth season)
- Luis Alfonso Mendoza (Latin America; Blue Mountain Mystery onwards)
- Fabrice Trojani (France and French speaking Canada)
- Juan Navarro Torelló (Spain)
- Wooden Railway (normal and birthday decorated)
- Take-n-Play (normal & talking)
- Collectible Railway
- Bachmann (G Scale, coming soon)
- Motor Road and Rail (Japan only)
- Wind-up (Japan only)
- Thomas and Friends Adventures (coming soon)