Toby, Trucks, and Trouble is the 32th book of The Railway Series published in 1988. The four stories are as follows.
- Mavis and the Lorry: Mavis is bringing trucks down from Anopha Quarry when she sees a lorry at the crossing, where vehicles often cross with dangerous speed and turns. The driver, who’s new to Sodor and didn’t expect to see an engine, has his lorry turned over when it collides with Mavis. Although the driver is unharmed but surprised, Mavis' cowcatcher is bent, and while she’s being mended Toby is sent to work at the quarry, leaving Percy with extra work.
- Toby's Seaside Holiday: Toby remiscises about his days working at a harbour in Yarmouth. One day, his crew told him they were allowed to go to a local village's seaside festival. After receiving brand-new paintwork, he set off to the village. After a night on a siding, Toby was told they didn’t have room for him, but the real reason was that they were afraid he would show everyone else up. However, Toby's daydream is interrupted when his crew returns. Toby leaves, noting the Fat Controller would have organised the whole event better.
- Bulstrode: Percy is told to go to Knapford Harbour to help with an emergency. There, the trucks ask him to unload their stone into Bulstrode, a cantankerous old barge, to get away from his constant complaining. Unfortunately as Percy starts to push, a coupling breaks and some trucks run into Bulstrode, who nearly drowns, but luckily for him the tide is out. The trucks are sad to lose their friends, but happy because they won’t have to deal with Bulstrode anymore. The workmen rescue some stone, Percy takes the broken trucks to the scrapyard, and Bulstrode is towed to a beach so children can play in him.
- Toby Takes the Road: Terence takes care of the shunting for Percy while he’s at the harbor, and brags about how he can "go anywhere and do anything". Then Toby goes to the quarry one frosty morning. At the crossing, the earth has swelled over the rails, derailing Toby and creating two long ruts in the road nearby. With some quick thinking on the fireman's part Toby gets back on the rails, and his crew spread some of his ashes to prevent that incident from happening again. The Fat Controller soon finds out, but all he says is that Toby should stick to the railway. Toby happily agrees.
This book contains examples of:
- Artistic License – History: 1020, the dirty and leaky steam engine Toby meets in "Toby's Seaside Holiday" is said to be younger than Toby; however, the J15/Y14 class to which 1020 belonged was built from 1883 to 1913, while Toby was built in 1914.
- Big Bad: Bulstrode.
- Be Careful What You Wish For: Bulstrode kept complaining about not getting his stone loaded quickly enough. He got his wish when a few stone trucks fell into his cargo hold and nearly sank him.
- Busman's Holiday: On his way to Great Yarmouth, Toby comes across a failing engine pulling a goods train and offers to help him.
- Call-Back:
- In "Mavis and the Lorry", the narration makes a reference to Thomas' encounter with the policeman.
- The opening paragraph of "Toby's Seaside Holiday" is a callback to Toby's first meeting with the Fat Controller and his move to the Island.
- The quay at Knapford Harbour slopes toward the sea, just as it did when Percy took the plunge.
- Fantastic Racism: Terence dabbles in this when he recommends the steam engines get rid of their rails so they can travel on roads as well.
- Historical Domain Character: In "Toby's Seaside Holiday", one illustration depicts Toby passing 8783, a D16/3 class locomotive. This was a real steam engine, built in 1923 and rebuilt after an accident in 1939. The original was scrapped in 1959, but a campaign to build a new D16/3 intended to reuse the number and name it "Phoenix".
- Laser-Guided Karma: Bulstrode's hulk is towed to a beach and left for children to play on.
- MacGyvering: After Toby derails at a crossing where frost had swollen the earth in the ruts beside the rails, his crew spread some of the ashes from his fire to thaw the soil and keep the track running properly.
- Pay Evil unto Evil: The trucks run into Bulstrode to get back at him for being so grumpy.
- Synchronous Episodes: The events of this book takes place during the events of Thomas and the Twins which wouldn't be published until a year later.
- Very Loosely Based on a True Story: "Mavis and the Lorry" and "Toby Takes the Road" were based on two real events on the Wishbech and Upwell Tramway.
- Whole Episode Flashback:
- The events of this book took place in 1987.
- In "Toby's Seaside Holiday", Toby tells Percy about his days working at Yarmouth, which the story is set between 1939 and 1948.
