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Image taken from “The Black Highwayman. (Being the second series of Black Bess.) [By Edward Viles.]”, London, 1868

The Highwayman is a charming and daring thief who relies on his powers of observation and personality to win the day. He is a swashbuckler and rogue, a fighter and spy, he is a master of Disguise. The highwayman is capable of great feats of skill and prowess when behind his mask. He is like a different person. A good highwayman may champion the poor, vowing only to steal from those who can afford it. An evil highwayman can be the most terrifying villain, slowly stealing not only trinkets, but secrets as well.

Originally Posted by bkdubs123 of the Wizards Community forums.

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You might say that the Highwayman is a fusion of sorts. He has the skill points of a bard, and as long as he remains disguised his attack bonus stacks up against a fighter‘s. His class skills resemble the rogue’s list of skills, and he is a thief first and foremost. Eventually the highwayman even picks up a few spells along the way from the schools of Illusion and Enchantment as well as some movement based spells thrown in to round out his arcane suite. Where the highwayman really shines is his two part life. One part mild mannered craftsman, the other dashing masked marauder. His abilities help him to sneak into vaults to steal treasure, sweet talk the lovely maiden on the way out, and if he is caught he can do a little fighting and make a break for it.

Game Rule Information

Alignment: Any Non-Lawful
Hit Dice: d6

Class Skills (6 + Intelligence Modifier per level, x4 at 1st level): Appraise (Intelligence), Balance (Dexterity), Bluff (Charisma), Climb (Strength), Craft (Intelligence), Diplomacy (Charisma), Disable Device (Intelligence), Disguise (Charisma), Escape Artist (Dexterity), Forgery (Intelligence), Gather Information (Charisma), Hide (Dexterity), Intimidate (Charisma), Jump (Strength), Knowledge (architecture and engineering) (Intelligence), Knowledge (local) (Intelligence), Knowledge (nobility and royalty) (Intelligence), Listen (Wisdom), Move Silently (Dexterity), Open Lock (Dexterity), Perform (Charisma), Profession (Wisdom), Ride (Dexterity), Search (Intelligence), Sleight of Hand (Dexterity), Spot (Wisdom), Swim (Strength), Tumble (Dexterity), Rope Use(Dexterity).

LvBase AttackFortRefWillSpecialSpellcasting
 Lv 1Lv 2Lv 3Lv 4
1+0+0+2+2Cover Identity, Masquerade +1, Trapfinding, Skill Focus (Disguise)1
2+1+0+3+3Combat Reflexes, detect law2
3+2+1+3+3Evasion, undetectable alignment2
4+3+1+4+4Quick Change31
5+3+1+4+4Masquerade +2 (Charisma to AC)32
6+4+2+5+5Opportunist Tactics32
7+5+2+5+5Slippery Mind331
8+6/+1+2+6+6Better Part of Valor432
9+6/+1+3+6+6Grand Entrance 1/day432
11+8/+3+3+7+7Skill Mastery4432
12+9/+4+4+8+8Improved Evasion4432
13+9/+4+4+8+8Spring Attack of Opportunity4443
14+10/+5+4+9+9Grand Entrance 2/day5443
15+11/+6/+1+5+9+9Masquerade +4 (True Masking)5444
16+12/+7/+2+5+10+10Dispel Scrying5544
17+12/+7/+2+5+10+10Hide in Plain Sight5554
18+13/+8/+3+6+11+11Freerunner 3/day5555
19+14/+9/+4+6+11+11Grand Entrance 3/day5555
20+15/+10/+5+6+12+12Masquerade +55555

Weapon and Armor Proficiency: A Highwayman is proficient with all simple and martial weapons, but only with light armor and no shields.

Cover Identity: At 1st Level the Highwayman adopts a cover identity. He chooses a Profession and uses this as his primary source of information. While performing under his cover identity the highwayman gets a +2 competence bonus to all Appraise , Craft, Gather Information, Listen, Profession, and Spot skill checks, but also a -2 circumstance penalty to all Bluff, Intimidate, and Sleight of Hand checks, and on all attack rolls. This cover is for gathering information only, not for flashy displays of prowess. The public must believe after all that the highwayman is just the neighborhood blacksmith.

Masquerade: At 1st level the highwayman begins to use his disguises to his advantage. While disguised as long as his Disguise is successful the highwayman gains a +1 circumstance bonus to all attack rolls, Intimidate checks, and all Strength and Dexterity based checks. A highwayman is filled with nearly supernatural confidence and ability while his Disguise goes unnoticed. This bonus increases by +1 at fifth level and every five levels thereafter. Once per day, per masquerade bonus, a Highwayman can produce as cause fear effect as the spell as long as he is successfully disguised. By 10th level, this effect is replaced by a Fear effect as the spell. These effects have a permanent duration so long as the Highwayman remains successfully disguised according to the effected creature, but the penalties apply only while the effected creatures are within line of sight to the Highwayman. At 5th level the highwayman further improves upon his prowess through performance and gains a deflection bonus to his armor class equal to his Charisma modifier as long as he is successfully disguised. At 10th level a highwayman gains the Never Outnumbered skill trick as a bonus skill trick. At 15th level a highwayman’s Disguise can resist even the most thorough scrutiny, foiling any Read Thoughts and true seeing spells targeting the highwayman or spell-like or supernatural abilities with similar effects.

Bonus Feats: At 1st level a Highwayman gains Skill Focus (Disguise) as a bonus feat and Combat Reflexes at 2nd level.

Spellcasting: A Highwayman has a very limited spell list (below) from which he draws arcane power. These spells are cast spontaneously, and each time a Highwayman gains a new level of spells he automatically knows every spell of that level. In order to cast a spell of a given level he must possess an Intelligence score of at least 10 + spell’s level. The DCs of any spells cast by a Highwayman are effected by his Charisma modifier. A Highwayman gains bonus spell slots per day for having a high Intelligence score.

Detect law: At 2nd level and higher, highwayman can detect law at will as a paladin detects evil.

Evasion: At 3rd level and higher, a highwayman can avoid even magical and unusual attacks with great agility. If he makes a successful Reflex saving throw against an attack that normally deals half damage on a successful save, he takes no damage instead. This ability does not function if the highwayman is wearing medium or heavy armor, or if the highwayman is rendered helpless.

Undetectable alignment: At 3rd level and higher, a highwayman’s disguises make it nearly impossible to determine his intentions. This ability functions exactly as the undetectable alignment spell except that it is always active as long as the highwayman is disguised.

Quick Change: By 4th level a highwayman has become adept at quickly changing from one identity to another. He can now don a Disguise in one-tenth the normal time (1d3 minutes) and don or remove armor in half the normal time.

Opportunist Tactics: At 6th level the highwayman has refined his combat style. With flashy movements and keen perception the highwayman gains the advantage over a fight. Anytime the highwayman would make a disarm or trip attempt as part of an attack of opportunity he gains a +3 bonus to his roll. Should he fail, he does not provoke further attacks of opportunity nor does he have a chance to be disarmed or tripped himself.

Slippery Mind: At 7th level and higher a highwayman gains a second chance to wriggle free from enchantment spells and effects. See the Rogue special ability, PHB 51.

Better Part of Valor: At 8th level the highwayman learns the value of discretion. During any round in which the highwayman does nothing but retreat from combat he (and any allies that do the same) gains a +4 circumstance bonus to AC. A highwayman is the perfect getaway man.

Grand Entrance: At 9th level once per day the highwayman can use his skills as a performer to fascinate his enemies. Upon entering a room the highwayman can use a flashy movement skill (Jump, ride, Tumble, or Use Rope) to fascinate his foes as a bard using bardic music of the highwayman’s class level. The save DC is equal to the highwayman’s check result and any Masquerade bonuses he may have also apply to the check roll. This effect lasts as long as the Highwayman can maintain the attention of those he has fascinated, and as long as neither he nor anyone else acts in any way hostile toward the fascinated creatures. A highwayman gets additional uses of this ability every five levels hereafter.

Skill Mastery: At 11th level the highwayman learns to control himself in stressful situations. Choose four of the highwayman·s class skills. The highwayman may take 10 on any of these four skills even in combat or other stressful situations.

Spring Attack of Opportunity: At 13th level the highwayman’s opportunistic combat style becomes second nature, and whenever he sees an opportunity to strike he takes it. Anytime a foe would take an action that provokes attacks of opportunity within half the highwayman·s movement speed the highwayman may attempt a Spring Attack toward that foe (to do this the highwayman moves from his space up to half his movement speed toward the provoker ending his movement in an empty space adjacent to the provoker and then attacks. This movement doesn’t provoke attacks of opportunity from anyone the highwayman threatens.) This ability can only be used once per round regardless of any extra attacks of opportunity the highwayman may have. If an enemy provokes an attack of opportunity but has no empty adjacent spaces the Highwayman cannot make a Spring Attack of Opportunity on that foe.

Dispel Scrying: At 16th level and higher a highwayman can dispel a scrying sensor as if targeting it with Greater Dispel magic. His caster level for this ability is his highwayman level +5. A highwayman can use this ability a number of times each day equal to 3 + his Charisma modifier.

Hide in Plain Sight: At 17th level the highwayman is able to find concealment where there is none to be found gaining the ability to use his Hide skill in any sort of urban setting or humanoid-built structure even while being observed.

Freerunner: At 18th level and higher a highwayman is capable of some of the most exceptional escapes imaginable. Three times each day the highwayman may produce either a freedom of movement or mind blank effect as the spells which last for 1 round. The freedom of movement effect can be used anytime at the Highwayman’s discretion, but the mind blank effect must be used immediately should he fail a save versus a mind-afflicting effect (so, if the highwayman fails a will save against suggestion he can, but does not have to, use up a daily use of Freerunner to apply mind blank).

Highwayman spell list

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