Highwayman CR 6
Str 12, Dex 18, Con 14, Int 13, Wis 8, Cha 10
Base Atk +6; CMB +10 (+14 when tripping); CMD 21 (23 vs. trip)
Feats Agile Maneuvers, Combat Expertise, Deceitful, Exotic Weapon Proficiency (spiked chain), Greater Trip, Improved Feint, Improved Trip, Weapon Finesse, Weapon Focus (spiked chain), Weapon Specialization (spiked chain)
Skills Acrobatics +14, Appraise +5, Bluff +12, Climb +5, Disable Device +11, Disguise +14, Escape Artist +10, Intimidate +4, Perception +7 (+8 to find traps), Ride +9, Sleight of Hand +8, Stealth +14, Swim +5
Languages Common, Halfling
SQ armor training 1, rogue talent (finesse rogue), trapfinding +1
Combat Gear potion of invisibility; Other Gear +1 chain shirt, +1 spiked chain, masterwork composite longbow (+1 Str) with 20 arrows, sap, cloak of resistance +1, disguise kit, light horse (combat trained) with saddle, silk rope, smokestick, thieves’ tools
Boon Highwaymen can allow the PCs to pass without being robbed, or they could attempt to steal an item or deliver a secret message directly to an NPC.
Highwaymen are notorious outlaws or flamboyant criminals who flaunt the law, prey upon innocent travelers, and revel in the discomfiture their predations have upon the local constabulary. Highwaymen love deception and trickery and elevate taunting to an art form. For highwaymen, the humiliation of an enemy can be more important than a successful heist. Highwaymen can be used as expert spies or scouts, or even as agile gladiators.
Two highwaymen might be the bodyguards of a guildmaster (CR 11), while a trio of highwaymen may serve as the henchmen of a bandit lord or bounty hunter (CR 12). A lone highwayman may lead a gang of a dozen bandits (CR 8) or travel with a minstrel and a pair of cavalry for his gang (CR 9).
Pathfinder RPG GameMastery Guide, © 2010, Paizo Publishing, LLC; Authors: Cam Banks, Wolfgang Baur, Jason Bulmahn, Jim Butler, Eric Cagle, Graeme Davis, Adam Daigle, Joshua J. Frost, James Jacobs, Kenneth Hite, Steven Kenson, Robin Laws, Tito Leati, Rob McCreary, Hal Maclean, Colin McComb, Jason Nelson, David Noonan, Richard Pett, Rich Redman, Sean K Reynolds, F. Wesley Schneider, Amber Scott, Doug Seacat, Mike Selinker, Lisa Stevens, James L. Sutter, Russ Taylor, Penny Williams, Skip Williams, Teeuwynn Woodruff.