Sergeant Major lives in Drill Hall and has the best kept garden in Shoe Town. His next door neighbor, however, is Trampy whose garden is completely overgrown with wild flowers, grass and weeds. This annoys Sergeant Major.
The Shoe People spend a day at the seaside. Flip-Flop is sun-bathing on the rocks when she is swept into the sea. Trampy, Charlie and Sergeant Major come to her rescue.
While daydreaming in his garden and being insulted by Sergeant Major, Trampy dreams of his past and how he first arrived in Shoetown. He has a very untidy lifestyle, but he is kind and generous and the other Shoe People love him for it.
The Shoe People are very excited. They have been invited to Swan Lake Cottage for a performance of Margot's latest ballet which she performs in her garden.
Charlie is the clown who lives at the Little Big Top. It also turns out that Sergeant Major wants a word with Charlie, who apparently squirted him with his flower once too often.
It's a rainy day in Shoetown, and Charlie, Sergeant Major and Wellington must help Margot get across a large puddle so she can get to the Shoetown Dance School.
Trampy falls asleep while reading the newspaper in his chair near the fireplace and dreams about the other Shoe People cleaning up his untidy house and garden. When Trampy wakes up, he realizes it was all a bad dream.
The Shoe People enjoy the fun of the rides and stalls at the fair. Margot and Bootee ride the Ferris wheel, but the two of them get stuck on the ride when the mechanism on the wheel gets jammed. Luckily, Charlie comes to their rescue.
A tree falls across the track at the railway station, and Mr. Potter, the station master, calls on the help of P.C. Boot and Sergeant Major. In the end, however, it is Charlie who comes up with the right solution.
A simple job for Margot by Sneaker who is clearing off the leaves on Margot's thatched roof with Charlie's tightrope and Trampy's ladder brings a warning from P.C Boot.
On a surprise visit to Margot's house, Charlie breaks a mirror by accident. The only way to replace it is to find one of his own mirrors from the circus, which does not have the normal "mirror" effect.
After laying a paper for P.C Boot, Margot, Charlie and Baby Bootie, Trampy settles down for an afternoon nap. However, Sergeant Major interrupts the trail mistaking the paper for litter, until he finds Trampy who explains about the trail.
Trampy offers to mow Sergeant Major's lawn but all does not go to plan, which leaves the lawn looking like a pile of spaghetti. Charlie has an ingenious plan to help Trampy cover up the mistake.
When Trampy was brought to the shoe repairer's, he was so worn out that he was beyond repair. The shoe mender was asked to throw him away. Trampy wasn't thrown away but put into the backroom of the shop, the room with a secret.
The Shoe People go on a mystery tour, but on the way to their destination, their bus gets lost due to Sneaker taking a broken signpost. Luckily, the tour ends well when the Shoe People finish their trip with a picnic outside the windmill.
The circus is supposed to come to Shoetown, but plans fall through when the show is canceled. Luckily, Charlie saves the day when he comes up with the idea of putting on a circus show with all the other Shoe People performing.
