Season 1

Tom the smooth talking tinker comes to town and Cuffy befriends him. He takes Tom around to meet all his friends, but they are wary of him and think he is shifty. Cuffy doesn't realize it until they both get arrested.

Cuffy goes on holiday, in town. On day two he gets bored and goes to see farmer Jake. By trying to help Mandy, he accidentally knocks Jake off his ladder.

A fashion designer uses Shillingbury as a back drop for his new line. Unfortunately, Cuffy manages to sneak into every shot until he is actually hired to be in the fashion show.

During a storm, Cuffy's roof leaks and he goes to Jake for help. Jake sends the vicar and he falls through Cuffy's roof. Cuffy goes back to Jake's and Mandy lets him stay for a night much to Jake's dismay. Accidents ensue and Cuffy is sent back to the caravan, only to find the vicar falling through the roof again.

Cuffy is offered the job as Janitor of the Village Hall. Mrs. Simkins points out that Cuffy does not contribute to the community. He takes charity and does odd jobs for money. So Cuffy takes the job.

The vicar's sister visits and Cuffy and Jake are both attracted to her. A competition for her affection begins, only to find she has a buyer for her house and has to leave.