Mary Smith, owner of the Black Swann inn is in debt to Sir John Glutton. Her son Nicholas tries to gather together the money by taking up the guise of the infamous highwayman Dick Turpin. Unfortunately for him, his first victim turns out to be the actual Turpin. When Nicholas is captured by Captain Spiker his mother, an old acquaintance of Dick, asks Turpin to take her son under his wing. The highwayman rescues the lad and gives him the nickname Swiftnick, after another rogue.
Dick thinks Swiftnick isn't cutting it as a highwayman and bribes Tanner the gunsmith into taking the boy in as an apprentice. Glutton and Spiker have come up with a plan to use an actress called Jane Kelsey, who main claim to fame is a performance as Cleopatra, to lure Turpin into a trap.
Turpin intends to find some rest in the little village of Mudbury, but Swiftnick starts bragging about Dick's skills as a prizefighter. An unsuspecting Dick soon finds himself facing the bully Hogg, the accomplice of bible thumping tax collector Father Nightingale. Dick decides to call a favor from an old friend, Tom "The Bristol Butcher" Bracewell, but he disappears shortly before the fight.
A poacher has cut in on Dick Turpins territory. Dick and Swiftnick decide to bait the most obvious suspect, a stranger named Joshua Vizard. Meanwhile Captain Spiker is thoroughly annoyed by the Sir John Glutton's visiting nephew, the extremely foppish Willougby.
When Dick and Swiftnick find themselves robbed, they pursue this masked highwayman, only to find the trail leading to a country house belonging to Mrs Bedingfield and her two daughters Belinda and Abigail.
Dick decides to fetch some of the loot his friend Sam Morgan the blacksmith has been keeping safe for him. Unfortunately, Morgan has just been captured by Spiker. Their first attempt at rescuing the blacksmith only results in freeing an old scoundrel called Isaac Rag. Therefor, Dick decides to take a hostage of his own, Sir John Glutton.
Glutton hires a man called Miller to pose as Turpin and discredit his name. Soon, even Swiftnick has fallen for the scam, as it appears that Dick Turpin has shot Nick's uncle Amos and stolen a pair of pistols.
Several members of 'The Brotherhood' have fallen into the hands of the law and been hanged. Suspecting betrayal by one of their own, Dick decides to visit the Brotherhood's leader, Tyson Sarney, aka the Upright Man.
The Duke of Hertford sends Colonel Moat to take care of Turpin after being robbed by him. Both Dick and Captain Spiker used to serve under Moat at Gibraltar. The old rivalry between the Captain and the Colonel soon rears up again, leaving Spiker demoted and Moat imposing a reign of terror.
Glutton has arranged a marriage between Spiker and the wealthy Phyllida Tranter. However, her less than impressive suitor Nigel Ffoulkes-Withers has followed her in a fit of desperation. Dick takes pity on the man and develops a plan to unite the young lovers.
Sir John Glutton sends Spiker on an errand carrying a letter pledging his allegiance to Prince Charles, pretender to the throne, in the seams of his coat. Spiker is ambushed by Foxy and Nabber, who steal the coat. Glutton forces Dick Turpin to recover the letter by holding Big Nell of the Cock and Bull hostage.
Swiftnick wants to get his name into songs as well and goes off on his own. He soon learns Glutton is terrorizing two children, Jem and Nan, at Rookham Hall. Meanwhile their mother, Glutton's niece, is being attacked by Foxy and Nabber, but Dick Turpin comes to the rescue.
By a strange order of events, Dick and Swiftnick find themselves thrown into jail at Slough together with Glutton and Spiker. Despite numerous attempts, the four of them seem to be done for, until by chance poor old Isaac Rag joins them in their cell.