This site is games | books | films

Richard ‘Dick Turpin’, Highwayman Legend

“Legendary Highwayman Dick Turpin: Outlaw, Romantic Figure, and Master of the Open Road!”

Richard 'Dick Turpin', Highwayman Legend
  • Alias: Gentleman Highwayman
  • Gender: Male
  • Race: Human
  • Occupation: Highwayman, Outlaw
  • Religion: Unknown
  • Allies: Fellow highwaymen, criminal associates
  • Enemies: Law enforcement, rival gangs, those who oppose his activities
  • Abode/Base of Operations: Hideouts in the English countryside, remote inns, forests
  • Nationality: English
  • Languages: English
  • Alignment: Chaotic Neutral
  • Affiliation(s): Independent, associated with various criminal networks
  • Significant Others: Mary Brazier (common-law wife)

Dick Turpin, a name that stirs tales of daring escapades and audacious heists, emerges as a larger-than-life figure in the annals of history. Turpin is an English outlaw and highwayman whose legendary exploits have become the stuff of legend. Roaming the highways and byways of the English countryside, he carves a path marked by audacity, danger, and a sense of romanticism that captures the imagination.

As a young man, Turpin initially embarked on a legitimate career as a butcher, but life’s twists and turns led him down a darker path. Faced with financial struggles and the allure of adventure, he chose to embrace the life of a highwayman, turning to the open road as his stage for audacious acts of robbery and cunning escapes. In his pursuit of riches and notoriety, Turpin adopts a charismatic persona, one that blends audacity with a touch of charm, making him a figure both feared and admired.

While Turpin is often associated with his daring robberies, he possesses a complex motivation that extends beyond mere greed. His life as a highwayman is an act of defiance against the rigid social structures of his time, a means to rebel against authority and make a name for himself. He thrives on the thrill of danger and the adrenaline rush that comes with each audacious escapade. Turpin’s escapades, while often illicit, are a reflection of his desire to challenge societal norms and become a legendary figure whose tales would be told for generations.

In the shadowy nights and mist-laden landscapes, Turpin’s reputation grows, and his cunning strategies make him a force to be reckoned with. His legendary rides, dramatic standoffs with the law, and mysterious escapes fuel the imagination of common folk and contribute to his aura as a folk hero. While his motives are not always noble, Turpin’s charisma and audacity make him a figure that captures the public’s fascination.

Ultimately, Dick Turpin’s tale is one of defiance, audacity, and a longing for a life that transcends the ordinary. His escapades represent a blend of adventure, rebellion, and a touch of romance in a time where the open road held both peril and promise. Whether seen as a criminal or a swashbuckling hero, Turpin’s legacy endures as a testament to the human desire for freedom and the allure of a life lived on one’s own terms.

Dick Turpin, Highwayman Legend

Medium humanoid (human), Chaotic Neutral

Armor Class 14 (leather armor) Hit Points 78 (12d8 + 24) Speed 30 ft.

12 (+1)16 (+3)14 (+2)12 (+1)10 (+0)14 (+2)

Skills Acrobatics +6, Deception +4, Perception +3, Stealth +6 Senses darkvision 60 ft., passive Perception 13 Languages Common Challenge 5 (1,800 XP)

Nimble Escape. Dick Turpin can take the Disengage or Hide action as a bonus action on each of his turns.

Evasion. If Dick Turpin is subjected to an effect that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.

Sneak Attack (1/Turn). Dick Turpin deals an extra 10 (3d6) damage when he hits a target with a weapon attack and has advantage on the attack roll, or when the target is within 5 feet of an ally of Turpin that isn’t incapacitated and Turpin doesn’t have disadvantage on the attack roll.


Multiattack. Dick Turpin makes two attacks: one with his rapier and one with his pistol.

  • Rapier. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d8 + 3) piercing damage.
  • Pistol. Ranged Weapon Attack: +6 to hit, range 20/60 ft., one target. Hit: 10 (2d6 + 3) piercing damage.
  • Quick Shot. Dick Turpin can use his bonus action to make a ranged attack with his pistol against a target he can see within range.


Evasion. When Dick Turpin is subjected to an effect, such as a red dragon’s fiery breath or an ice storm spell, that allows him to make a Dexterity saving throw to take only half damage, he instead takes no damage if he succeeds on the saving throw, and only half damage if he fails.

Legendary Actions

Dick Turpin can take 3 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Turpin regains spent legendary actions at the start of his turn.

Quick Shot. Dick Turpin makes a pistol attack.

Disengage. Dick Turpin takes the Disengage action.

Dash. Dick Turpin takes the Dash action.

Lair Actions

On initiative count 20 (losing initiative ties), Dick Turpin can take a lair action to cause one of the following effects; he can’t use the same effect two rounds in a row:

Ambush. Dick Turpin and his allies become invisible until they attack or cast a spell.

Concealing Shadows. Magical darkness spreads from a point within 60 feet of Turpin, creating an area of darkness that lasts until initiative count 20 on the next round.

Intimidating Presence. Turpin targets one creature he can see within 30 feet of him. If the target can see Turpin, the target must succeed on a DC 14 Wisdom saving throw or be frightened until the end of its next turn.


Dick Turpin wears leather armor, wields a rapier, and carries a pistol.

Magical Pistol. This finely crafted pistol grants advantage on ranged attacks when used by Dick Turpin. It has 6 charges and regains 1d4+1 expended charges daily at dawn.

Turpin’s Mask. A black mask that grants advantage on Stealth checks and disguises Turpin’s identity when worn. It also grants him advantage on Charisma (Deception) checks when trying to pass himself off as another.

Amulet of Evasion. This amulet allows Turpin to use his Evasion ability twice between short rests.

Currently in the World

Dick Turpin stands at an average height, his lean and wiry frame accentuated by his clothing, which is a mix of rugged attire and a touch of refined fashion. His dark, unkempt hair cascades over his shoulders, framing a face that bears the signs of a life lived on the edge. His piercing eyes gleam with a mix of confidence and mischief, a reflection of the daring life he leads. Turpin’s attire is a combination of dark leather and well-worn fabric, a practical ensemble that allows him to move swiftly and silently through his surroundings.

Currently, he finds himself in the heart of a dense forest, the leaves overhead casting dappled shadows on the ground. Concealed behind the thick foliage, he observes his surroundings with a mixture of caution and excitement. The air is crisp, and the distant sounds of rustling leaves and chirping birds create an ambiance of serene isolation. Turpin’s mood is a curious blend of anticipation and readiness, for he knows that at any moment, he might find himself engaged in a daring encounter or a hasty escape. His senses are heightened, and his fingers rest lightly on the hilt of his trusty weapon, prepared for whatever the wilderness might throw his way.

Scroll to Top