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The Highwayman is one half of the pair of heroes you'd get at the beginning of Darkest Dungeon. In Darkest Dungeon 2, he is still one of the first characters you have unlocked, but his Crusader buddy is currently missing.

RELATED: Darkest Dungeon 2: How To Make An Overpowered Plague Doctor

In this game, the Highwayman fits the rogue archetype quite perfectly. He's great when it comes to inflicting ranged damage, is able to move around the party a little, and can even steal positive status effects from the enemies - and this is definitely something you'll want to capitalize on. Overall, he's a very solid character to have in the middle ranks.

Updated on May 31, 2023 by Matt Arnold: The Highwayman remains a core Hero in many DD2 lineups, even after the game has launched out of early access. Learning to use this versatile damage-dealer will go a long way toward getting you a victory at the Mountain. Keep reading to learn how!

Highwayman Skills

Darkest Dungeon 2 Highwayman Mastery Trainer
The Mastery Trainer screen for the Highwayman in Darkest Dungeon 2

The Highwayman is a very mobile Hero, but is best when he's in the first or second Rank. It's usually best to focus on dealing damage and evading enemy buffs, keeping his movement Skills in reserve to quickly reconfigure your party if your formation gets shuffled.

Skill

Highwayman Rank

Enemy Rank

Effects

Mastery Upgrade

Wicked Slice

1, 2, or 3

1 or 2

  • Melee attack for 4-8 damage.
  • Fifteen percent crit chance.
  • Ignores up to 20 Death Resistance.

  • Increases minimum damage by two and maximum damage by one.
  • Increases crit chance to twenty percent.
  • Ignores an additional 10 Death Resistance.

Pistol Shot

2, 3, or 4

2, 3, or 4

  • Ranged attack for 3-6 damage.
  • Ten percent crit chance.
  • Combo bonus: Inflicts Daze on the target.

  • Increases the minimum damage by one and maximum damage by two.
  • Increases crit chance to fifteen percent.
  • Inflicts Stun instead of Daze.

Duelist's Advance

2, 3, or 4

1, 2, or 3

  • Melee attack for 3-5 damage.
  • Five percent crit chance.
  • The Highwayman moves forward one space.
  • The Highwayman gains two Riposte tokens.

  • Deals an additional point of damage.
  • Increases crit chance to ten percent.
  • The Highwayman gains an additional Riposte token.
  • The Highwayman also gains a Dodge token.

Tracking Shot

Any

2, 3, or 4

  • Non-damaging Ranged attack.
  • Places a Combo token on the target.
  • Ignores and removes Stealth and/or Dodge.

  • The target cannot gain Dodge tokens for the next two rounds.

Take Aim

Any

N/A

  • The Highwayman gains a Crit token.
  • The Highwayman gains a Dodge token.
  • Removes Blind from the Highwayman.
  • One-turn cooldown.

  • The Highwayman gains an additional Crit token.
  • The Highwayman also gains a Speed token.

Point Blank Shot

1

1

  • Ranged attack for 6-12 damage.
  • Ten percent crit chance.
  • The Highwayman and the target each move back one space.
  • Places a Combo token on the target.

  • Increases minimum damage by four and maximum damage by one.
  • Increases crit chance to fifteen percent.

Grapeshot Blast

2, 3, or 4

1 and 2

  • Ranged attack for 2-4 damage to each target.
  • Five percent crit chance.

  • Deals two additional damage to each target.
  • Increases crit chance to ten percent.

Open Vein

1, 2, or 3

1 or 2

  • Melee attack for 3-5 damage.
  • Five percent crit chance.
  • Inflicts two stacks of Bleed on the target.
  • Combo bonus: Doubles the number of Bleed stacks inflicted.

  • Deals an additional point of damage.
  • Increases crit chance to ten percent.
  • Inflicts an additional stack of Bleed.
    • This stack is doubled like the rest if the target has a Combo token.

Double Tap

2 or 3

2 or 3

  • Ranged attack for 4-8 damage.
  • Five percent crit chance.
  • If the target's HP is below thirty percent of its maximum, Double Tap deals thirty percent more damage.
  • Ignores up to 10 Death Resistance.

  • Increases minimum damage by two and maximum damage by one.
  • Triggers the damage bonus if the target's HP is below half of its maximum.
  • Ignores an additional 10 Death Resistance.

Highway Robbery

2, 3, or 4

1, 2, or 3

  • Can only target enemies that have one or more positive (gold) tokens.
  • Non-damaging Melee attack.
  • Ignores Dodge.
  • Removes up to two positive tokens from the target.
    • If the target has more than two positive tokens, two are selected at random.

  • One-turn cooldown.

  • The Highwayman gains a copy of each token removed.

Double Cross

1 or 2

1 or 2

  • Melee attack for 2-4 damage.
  • Five percent crit chance.
  • The Highwayman gains a Block token.
  • Inflicts Vulnerability on the target.

  • Deals an additional point of damage.
  • Inflicts an additional stack of Vulnerability.

Double Tap and Double Cross are some of the few attack Skills that do not increase their crit rates when upgraded.

Highwayman Shrine Battles

Darkest Dungeon 2 shot showing highwayman, hellion, plague doctor, and leper in front of a stagecoach

The Highwayman has two Shrine of Reflection battles that grant him skills - one on the first Shrine visit and one on the fourth. These encounters detail his career as a roadside robber.

First Shrine Visit: Freedom

Darkest Dungeon 2 Highwayman Shrine Battle Freedom
The Highwayman's first shrine battle: Freedom. Darkest Dungeon 2

While four against one seems tough, this battle is actually quite easy. The guards here have very low health and can be taken out swiftly with a combination of Lunging Cuff and Knee Strike.

When a guard has a Sound the Alarm token, use Stone Missile to remove it before you get pushed back. Knee Strike them all to death and you'll obtain your first extra ability.

Fourth Shrine Visit: Highway Robbery

Darkest Dungeon 2 Highwayman Shrine Battle Highway Robbery
The Highwayman's second shrine battle: Highway Robbery. Darkest Dungeon 2

This battle is quite the puzzle boss fight. This time, you're up against a coach that will keep making reinforcements for you to fight.

The trick to this battle is keeping the pressure upon the coach by targeting it with attacks but taking out the guards every now and then to give yourself some breathing room. If they manage to push you back, you'll take some Stress damage and that's not good.

Once the coach is defeated, you can mop up and receive your prize.

Best Builds For Each Highwayman Path

Darkest Dungeon 2 Highwayman Double Cross
The Highwayman using Double Cross in battle in Darkest Dungeon 2

Choosing a Path for the Highwayman will specialize him toward Melee or Ranged attacks, usually at the expense of the other. His inherent versatility also makes him worth keeping as a Wanderer so that he can step in for fallen Heroes as needed.

Path

Effects

Recommended Skills

Recommended Trinkets

Wanderer

  • Gain an extra Candle at the end of the run.

  • Wicked Slice
  • Open Vein
  • Duelist's Advance
  • Point Blank Shot
  • Highway Robbery

  • Sharpness Charm (any tier)
  • Heartseeker (any tier)
  • Cursed Coin
  • Rat Skull
  • Clasp Knife

Rogue

  • Point Blank Shot gives the Highwayman a Riposte token in addition to its other effects.
  • The Highwayman deals twenty-five percent more damage when he's in Rank 1.
  • The Highwayman deals twenty-five percent less damage when he's in Rank 3.
  • The Highwayman deals half damage when he's in Rank 4.

  • Wicked Slice
  • Open Vein
  • Duelist's Advance
  • Point Blank Shot
  • Double Cross

  • Sharpness Charm (any tier)
  • Heartseeker (any tier)
  • Rat Skull
  • Tormenting Locket
  • Dark Impulse (Movement)
  • Jealous Whisper

Sharpshot

  • Grapeshot Blast gives the Highwayman a Strength token in addition to its other effects.
  • The Highwayman's Ranged attacks deal twenty-five percent more damage.
  • The Highwayman's Melee attacks deal twenty-five percent less damage.
  • Increases the Highwayman's Speed by three.

  • Pistol Shot
  • Take Aim
  • Grapeshot Blast
  • Point Blank Shot
  • Double Tap

  • Sharpness Charm (any tier)
  • Heartseeker (any tier)
  • Wolfsblood (any tier)
  • Raven's Reach
  • Snappy Swig
  • Dark Impulse (any)
  • Snap Judgment

Yellowhand

  • Increases the Highwayman's maximum HP by fifteen percent.
  • Highway Robbery steals an additional token.
  • Double Cross removes a stack of Block from the target before applying Vulnerability.
  • The Highwayman's Melee attacks reduce their targets' Bleed Resistance by 10 for three rounds, in addition to their other effects.
  • The Highwayman's Ranged attacks deal seventy-five percent less damage.

  • Wicked Slice
  • Open Vein
  • Duelist's Advance
  • Highway Robbery
  • Double Cross

  • Sharpness Charm (any tier)
  • Heartseeker (any tier)
  • Hale Draught (any tier)
  • Cursed Coin
  • Rat Skull
  • Tormenting Locket

Wanderer

Open Vein is a great Skill for draining HP from large enemies, especially when it's used alongside other Heroes' damage-over-time effects. When it's time to finish off an enemy, Wicked Slice bypasses Death Resistance, making it easier to get the killing blow. Upgrading Highway Robbery is always a good use of Mastery Points, as it lets you remove enemy buffs and apply them to the Highwayman instead!

Rogue

The Highwayman's up-close-and-personal Melee build excels when he's at the front of the party, but quickly loses effectiveness the further back he moves. Try to Immobilize the Highwayman (or the Heroes behind him) to keep him in the front rank, or simply alternate between Point Blank Shot and Duelist's Advance to quickly carve through the foes in front and keep Riposte active.

Sharpshot

Lurking in the second or third rank, the Sharpshot can make quick work of the middle of the enemy formation. Start him in the front of your team, taking advantage of his high Speed to open every fight with Point Blank Shot, dealing massive damage before the Highwayman settles into his rhythm for the rest of the battle.

Double Tap deserves special mention as one of the game's best Skills for finishing wounded enemies. Between its damage bonus, Death Resistance piercing, and the Sharpshot's enhancements, this Skill has the potential to prevent dangerous enemies from getting one last hit in before they die.

Yellowhand

Like the Rogue, the Yellowhand is at his best when he's at the very front of the party. He removes enemy buffs with ease, making him a huge asset against Cultists.

This Path maintains the Highwayman's overall damage potential, but you're likely to find that you'll be using his support and setup Skills, such as Double Cross and Highway Robbery, more often. For that reason, the Yellowhand is best used in a secondary damage role.

NEXT: Darkest Dungeon 2: How To Make An Overpowered Man At Arms