These delightful stories take place in and around Pear Tree Farm, where the Richards family believe they have a working dog called Ollie the Collie. Ollie however has other ideas. He is a dog with attitude! A fully paid-up member of the canine awkward squad and as far as he is concerned a pet. If there is an easy way, Ollie will take it, yet somehow, he always seems to win the day.
Williams's Watch It is harvest time on Pear Tree Farm. Mr. Richards can't wait to use his gleaming new combine harvester but, Ollie would rather wallow in the duck pond, than help with the harvest. Despite several setbacks, Thirty-Acre Field is harvested in record time, but everyone looks at the vast expanse of stubble in dismay when William, the farm hand tells them he has lost his watch.
The Hero Of Bluebell Wood Everyone is hoping that the duck eggs Ollie has found by the pond, will help to improve Mrs Richards dreaded cakes. While Mrs Richards is busy in her kitchen, Dudley, the postman, is knocked off his bike by a white van speeding towards Bluebell Wood. The Richards children, go to the wood to investigate. Soon, everyone is convinced that Arnold Pegg, the agricultural engineer, is stealing bluebells, but not Ollie, he has other ideas!