- "How some shoddy Shepherd managed to evade Aura's best man with a flock of sheep is simply beyond me."
- ―Aura's Grunt, Samson, Boco, and the Man in the Hills
The Shepherd is a mysterious herdsmen who wanders the hills of Sodor.
The Shepherd has been seen around many parts of Sodor with his flock of sheep. At some point, he became the possessor of Proteus' lamp, carrying it with him on his journeys through the landscape. His possession of the lamp became of interest to Sir Frederick Aura, and Walter Richards was dispatched to collect it. While near the Culdee Fell Railway one day, the lamp began glowing, and a beam of energy shot upwards out of the lamp. From this beam Proteus delivers a prophetic statement. Not long after, a radio reports Culdee had an accident nearby, distracting the onlooking Mr. Richards. This allows the shepherd to escape with the lamp.
After this incident, the Shepherd continues to evade Aura. However, once the Man in the Hills begins appearing in new locations beyond Green Hills Junction, Aura sends his grunts to investigate one such etching near the Crovan's Gate Mine. Suspecting these etchings are somehow related to the Shepherd, Aura orders his grunts to draw him out while not bringing attention to themselves. When the shepherd fails to show himself, one of the grunts proceeds to shoot the etching with a rocket launcher, endangering BoCo and Samson below, drawing attention to Aura's operation. As such, Aura quickly terminates the two.
The Shepherd then retreats into the mountains of Culdee Fell. On the bridge overlooking Poll-ny-Chrink, the Lamp begins to carve a Man in the Hills etching in a cliff face above the bridge, confirming the carvings to be the work of the lamp. The jolt from the lamp causes a power surge on the bridge, throwing the Shepherd off the bridge. He as able to catch a bridge support with his crook, holding onto it and the lamp for dear life.
The Search and Rescue Centre and Aura are quickly notified, both of which send parties to investigate. Harold attempts to rescue the shepherd via a rope, but the shepherd refuses to let go of either the crook or the lamp. Harold then flies to Shiloh, where he meets Culdee, advising him to go and rescue the shepherd by rail. After Aura stages an accident at Kirk Machan which traps all the other engines, Culdee musters up his courage to save the shepherd himself.
Richards and Culdee arrive at the scene concurrently. In light of their being too many witnesses, Richards is instructed not to shoot the shepherd. While he looks on from a distance, Culdee, Catherine, and his driver attempt to coax the Shepherd to drop the lamp. After much consideration, the Shepherd decides to drop the lamp, and Mr. Richards follows the lamp into the Chrink. Upon returning to Kirk Machan, the Shepherd is looked over and questioned by the Doctor, still unable to utter a word following his ordeal.
- Season 1: Snow Blind (flashback cameo)
- Season 2: Blunderbuss (cameo), All the World's a Stage (cameo), Swashbuckler (cameo), Thomas and the Fortune Teller (cameo)
- Season 3: Logan Leaves his Mark (does not speak), Samson, BoCo, and the Man in the Hills (does not speak), Culdee Fell (does not speak)
- Web Clips: Mike and Frank Banter: SLOTLT, ScarletFire, and EE93's Return (cameo)