The High Toby: Being further chapters in the life and fortunes of Dick Ryder, otherwise Galloping Dick, sometime gentleman of the road

In Short

This collection of highway adventures follows Dick Ryder, self-styled "Galloping Dick," as he rides the seventeenth-century roads of England. Operating mainly alone, Ryder relies on quick wits, a sharp blade, and an theatrical sense of bravado to hold up coaches, outsmart rival rogues, and evade the law. Across eleven interconnected episodes, he moves between lonely heaths and crowded taverns, tangling with corrupt judges, desperate lovers, and treacherous former partners. The book endures because of Ryder’s irresistible, buoyant voice—a blend of roguelike vanity, sudden chivalry, and an unquenchable thirst for the open road.

The Story

The narrative follows the exploits and close calls of Dick Ryder, a highwayman who proudly works the English roads alone, shunning permanent partnerships after early betrayals. The opening sees Dick navigating the treacherous December nights near Petersfield, where he crosses paths with Sir Gilbert. Having kidnapped young Mrs. Barbara for his own ends, Sir Gilbert attempts to buy Dick off with ten guineas. Spotting the lady's distress, Dick takes the money but refuses to surrender her, choosing instead to protect the woman and outmaneuver her captor.

Dick’s travels frequently plunge him into the affairs of strangers. At an inn, he encounters the pretty, doll-faced Miss Nancy and her hesitant lover, Mr. Riseley. When the boisterous, drunken Captain "Old Irons" attempts to interfere, Dick steps in to orchestrate a tense supper party that shields the young couple from ruin. Soon after, he intercepts a grand chaise containing a sharp-witted noblewoman and her delicate niece. Though the elder lady attempts to dismiss him with twenty guineas, Dick finds himself captivated by the niece’s quiet dignity. Retiring to the darkness, he risks capture by returning to the inn simply to ensure the girl remains unharmed by her tyrannical relative.

His boldest encounters bring him face-to-face with the law itself. In a packed courtroom, Dick trades dangerous verbal barbs with the infamous Lord Chief Justice Jeffreys. Recognizing the judge's ruthless nature, Dick bluffly impersonates a helpful citizen to trick Jeffreys' butler, securing an escape right under the noses of the authorities. In another episode, he rescues a young woman and her household from "York," a charming fop who is secretly a ruthless thief.

When not dodging the law, Dick deals with old rivalries. He clashes with Creech, an unprincipled tobyman who boasts of a loot bag containing eight hundred golden guineas and a casket of queen’s jewels. Through a tense game of dice and a swift pistol-butt to Creech’s skull, Dick claims the treasure and leads a high-speed horseback pursuit across the plain to return the jewels to their rightful owner.

Toward the journey's end, Dick aids an escaped gentleman, guiding him through blinding snowstorms to an inn while dodging the relentless thief-taker Timothy Grubbe. In his final recorded adventure, Dick accompanies a naïve young Sussex gentleman named Masters, who is chasing a false romance. Discovering the bride's infidelity, Dick delivers a stark, midnight lesson at her doorstep before riding away into the dark.

How It Unfolds

The encounter on the heath While traversing the cold Portsmouth Road, Dick intercepts Sir Gilbert and his captive, Mrs. Barbara. He cleverly accepts a ten-guinea bribe before turning the tables on Sir Gilbert to secure the lady's freedom.

A tavern intervention Stopping at an inn, Dick discovers young Miss Nancy and her suitor cornered by the loud-mouthed Captain "Old Irons." Dick joins their table, using his commanding presence to diffuse a dangerous confrontation.

The hold-up of the chaise Dick halts a carriage bearing an ill-tempered noblewoman and her gentle niece. After accepting the aunt's bribe, he returns under cover of darkness out of concern for the young niece's safety.

Facing the bench In a crowded court, Dick engages in a perilous battle of wits with the feared Lord Chief Justice Jeffreys. He escapes by tricking a naive house butler into letting him slip away through a side door.

The duel with Creech Dick tracks down his former associate, the crude robber Creech, in a local tavern. After outsmarting Creech in a game of chance and knocking him out with a pistol, Dick leads a thrilling chase across the plains to return stolen jewels.

A night in the snow Surrounded by a sudden blizzard, Dick assists a delicate noblewoman whose horse stumbles in a drift. He safely conducts her to a warm inn, ensuring she is reunited with her travelling party.

The midnight reckoning Dick travels alongside young Squire Masters to the home of a deceitful bride. Arriving at late hours, Dick exposes the woman's treachery, leaving her swooning on the doorstep as he canters back into the night.

The People

• Dick Ryder ("Galloping Dick"): An independent, proud highwayman who prides himself on his gentlemanly manners, sharp tongue, and superior horsemanship. Though a thief by trade, he operates under a personal code of honour, frequently risking his skin to aid distressed maidens or outwit corrupt men of power.
• Sir Gilbert: A smooth-talking, cold-hearted gentleman who attempts to manipulate Dick into surrendering a captive woman. His calm demeanor hides a calculating, ruthless ambition.
• Creech: A coarse, boastful robber and former acquaintance of Dick. Driven purely by greed and liquor, he lacks Dick's polish, leading to a fiery showdown over a casket of stolen jewels.
• Lord Chief Justice Jeffreys: A feared, hot-tempered magistrate with "woman's eyes" and an acute instinct for spotting rogues. He represents the absolute power of the state that Dick continuously evades.
• Timothy Grubbe: A persistent thief-taker who continuously stalks Dick across various shires, eager to earn the reward for the highwayman's capture.
• Squire Masters: A gullible, romantic young man from Sussex whose innocence contrasts sharply with Dick's worldly cynicism.

In Its Own Voice

"I ever had the name of one that kept to himself, nor was bedfellow to none upon the high toby." Dick introduces his solitary philosophy on the open road.

"Why, set me down in your accounts as Galloping Dick of the Roads, and debit me with what you will." Dick boldly announces his identity during a night carriage robbery.

"Damme! no one shall say I am no gentleman, for I am that afore everything else, as I will prove on any buck's body." Dick defends his personal honour when questioned by a young woman.

What It's Really About

Behind the thundering hooves and drawn pistols, the book explores the precarious nature of freedom in a heavily stratified society. Dick Ryder’s refusal to join highway gangs reflects a deep mistrust of institutions and temporary alliances alike. His code of conduct highlights the hypocrisy of the period's upper classes; wealthy gentlemen and powerful judges often act with far greater cruelty than the outlaw who robs them. Ultimately, the stories examine what it means to be a "gentleman"—suggesting that true chivalry, courage, and fairness are found not in courtrooms or manor houses, but under the moonlight on the open heath.

Why Read It Today

Readers who enjoy classic swashbuckling tales like The Scarlet Pimpernel or the historical adventures of Rafael Sabatini will find much to admire here. Watson writes with an energetic, rhythmic style that immerses the reader in the atmospheric, lantern-lit world of late seventeenth-century England. The prose is rich with authentic period slang—terms like "rumpad," "tobyman," and "barkers" abound—which gives Galloping Dick’s first-person narration a vibrant, distinct voice. While the episodic nature means there is no single overarching plot, each story delivers a tight, satisfying dramatic arc filled with suspense, sharp dialogue, and memorable escapes. It offers a spirited escape into a vanished world of rogues and midnight rides.