Dismas the Highwayman

Dismas was a highwayman until he committed a crime he wishes he could take back. Now he roams the road, looking for redemption.

Who Is Dismas the Highwayman?

Who Are Dismas the Highwayman?

Not much is known about Dismas, the Highwayman. He’s a bandit, traveling the old road in search of redemption for a crime he regrets commiting. Upon reaching the Hamlet, he attempts to redeem himself by teaming up with the misfit heroes traversing the Darkest Dungeon. Knowing the difficulty of that game, he probably dies. Oops.

But before dying, Dismas brings some much needed straight damage from any position to his team. That's a big deal, in a game with a lot of forced movement. Plus, he’s got a few movement shenanigans of his own to help after the Crusader gets yeeted to the back row.

When it comes to damage, Dismas uses a combination of blade and gun. He hits hard, often applying bleed. And unlike Pathfinder, in Darkest Dungeon bleed STACKS. It's like, my go-to strategy.

Darkest Dungeon is easily one of my favorite games of the past decade and one of my favorite indie games ever. It's a great combination of mechanics – roguelike, party-management and tactics – all up my alley. Plus, the punishing difficulty makes wins feel good, and it manages to mostly not feel unfair.

The Highwayman is one of the first two classes introduced in the game, and I was hooked on his slice and shoot gameplay immediately. The first time I discovered Point Blank Shot, I rarely used anything else for a while. Let's hope it translates.

Keys to the Character

Dismas' dagger and pistol

Stabby McShooty

Dismas deals damage. How that damage gets dealt can vary – he is equally comfortable up close (with a dagger) and further away (with a pistol).

Mysterious locket

Road Regrets

Dismas was a brigand preying on the coaches that travelled the old road, until he was set up to rob the wrong coach. Now, he travels with regret over the mysterious crime.

Dismas' scarf

Scarf Season

Dismas is a former criminal. Now, he hides his face – out of both stealth and shame. Luckily, he has a sweet red scarf to hide it for him.

Bloody dagger

That’s Bloody Sharp

The blade strikes bleed out foes over time, before the pistol blasts fools from a distance. It’s a match made in heaven (or the Hamlet).

Building Dismas the Highwayman

Dismas doesn’t bring too much to the table outside of pure damage and a dour attitude, but at least he is good at those things.

On the tabletop, Dismas is less reliant on positioning than many other melee or ranged attackers, due to his preference of a dagger and a gun. These dual weapons ensure that he has a target every turn, often without needing to move to stay in range.

He does benefit from being in melee range, though. As he progresses through the build, Dismas can unlock some bleed potential on the dagger. As well, feats like Sword and Pistol allow him to take ranged shots from up close, without triggering Attacks of Opportunity.

Outside of battle, Dismas' Legendary Intimidation and Thievery can help procure valuables and access for the party, and his high Stealth can get him into most places unseen.


· ·
· · ·
· · · ·
· · · · ·
· ·
· · ·
· · · ·
· · · · ·
· ·
· · ·
· · · ·
· · · · ·
· ·
· · ·
· · · ·
· · · · ·


Human – Versatile

Dismas is human, like all of his allies on the Old Road (well, maybe except for the Abomination). The Versatile heritage gives him one extra General Feat, which he will need to survive the darkest dungeon.

Level Feat Notes
1 Natural Ambition - Sword and Pistol The basics of the build in one compact feat.
5 General Training - Diehard The road is dangerous, best to be unwilling to die.
9 Hardy Traveler It takes more than the road to bring down a highwayman. He's exceptionally well-travelled.
13 Bounce Back Hopefully Dismas can do this without visiting any of the stress relievers in town.
17 Advanced General Training - Feather Step Movement shenanigans are always welcome in DD.



Dismas spent years preying on travellers on the old road. Those days are behind him now, but he has kept with him many helpful lessons from those experiences. Plus, a pretty grim locket.


Gunslinger – Way of the Drifter

Dismas gets a ton of his flavor right out of the gate from The Way of the Drifter. As he progresses, it provides the movement abilities, reloading abilities and interesting ways to combine his two weapons. It’s perfect.

However, Dismas isn’t just a gunfighter, he’s a criminal. Therefore, taking the Rogue Dedication early is a great way to gain some of those more nefarious traits.

Level Feat Notes
1 Dual-Weapon Reload This is the feat that makes the pistol use even possible. Reload without a free hand.
2 Rogue Dedication - Subtle Theft He's not just a gunslinger, he's a criminal. This allows some important aspects of the character down the road.
4 Sneak Attacker Extra damage on many of Dismas strikes, if he is attacking the right targets.
6 Drifter's Juke The move-and-strike gameplay we know and love from Dismas.
8 Basic Trickery - Nimble Dodge Another escape from melee range without triggering a smack.
10 Rebounding Assault A bit more flair that Dismas traditionally is known for, but man does it look cool.
12 Advanced Trickery - Twist the Knife Bleeds, finally.
14 Two-Weapon Fusillade An attack with each weapon, with one action.
16 Hair Trigger Start shooting almost immediately when encounters begin.
18 Final Shot The "Point Blank Shot" from DD, Pathfinderized.
20 Perfect Readiness Always ready to dash away or load the pistol.

Skills & General Feats

Dismas' intimidation is a little different than that of a ferocious warrior, like Barret. Instead, Dismas raises the stress level of his foes through Gallows Humor, and a general depression.

Thievery is as usual though. He also dabbles in Occultism to know the enemy – any edge is helpful in the Darkest Dungeon.

Legendary: Intimidation, Thievery
Master: Stealth
Expert: Occultism

Level Feats Notes
2 Intimidating Glare The look he'd give the riders of the carriages on the old road.
3 Fleet Gotta be faster than the enemy to keep the upper (under)hand.
4 Cat Fall Land more gracefully and strike sooner.
6 Steady Balance With a high Stealth, it can be important to be able to access precarious positions.
7 Expeditious Search Make sure to get all those valuables.
8 Quiet Allies Don't let allies give up Dismas position.
10 Quick Unlock Get in, get out, regret the crime.
11 Incredible Scout Dismas is ready to watch the road, like a true Highwayman.
12 Swift Sneak Being sneaky is one thing, being sneaky and fast is a whole other.
14 Terrified Retreat Get foes running from the Highwayman's vibe.
15 Legendary Thief Steal anything, keep the locket.
16 Skeptic's Defense Can you be affected by what you don't believe in?
18 Battle Cry Wonder what the Gallows Humor battle cry sounds like?
19 Scare to Death Easier than shooting or stabbing: scaring.
20 Armored Stealth Dismas the Highwayman wants to be in the thick of it, he should stay safe.

Attribute Increases


Suggested Starting Equipment

Dismas the Highwayman's Signature Items

Key Spells


Dismas the Highwayman Resources