Encounters: Highwaymen

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Roll 1d10. After using an encounter, remove it and write a new one.

Wilds

• 1 rookie highwayman in need of robbery experience. Wants to apply to a highwayman company.
• 2 servants of highwaymen interview the party to determine if they are worthy of being robbed.
• 3 highwaymen and their dog on a picnic in beautiful landscape, discussing the finer points of highway robbery.
• 4 fans looking for their highwayman idol, Danil the Dagger-Demon.
• 5 highwaymen ride up to the party and congratulate them on the honor of being robbed by the Crimson Crossbows.
• 6) Insolvent noble tries highway robbery, along with 5 servants. Dislikes the uncomfortable wilderness.
• 7 dwarven highwaymen. Methodical and professional. Ask for an inventory of the party’s valuables to calculate whether they are worth stealing.
• 8) 3 highwaymen meeting 5 aspirants hoping to join their company, questioning them and testing their skills.
• 9) 5 highwaymen robbing 4 traders. One trader secretly in love with the highwayman leader.
• 10 highwaymen of the absolute elite. Will only rob royalty and high nobility. They laugh at the party’s poverty and raggedness.

 

Rural

• 1 noble was rude to a highwayman company, who took his money, his horse, his servants, and his clothes. Furious, wants revenge.
• 2 highwaymen visit the village leader to discuss buying intel on passing rich travellers.
• 3) 2 lovestruck youths compete for the affectations of a visiting highwayman.
• 4 highwaymen ride through the village with great pomp and circumstance. Villagers fascinated.
• 5 highwaymen hiding from pursuing soldiers in a friendly farmer’s barn.
• 6 highwaymen arrange a dance at the village green.
• 7 highwaymen forced to stay at cheap inn. Disgruntled.
• 8) 5 highwaymen meet 3 fences to sell stolen goods.
• 9 highwaymen crash the local economy through excessive spending of stolen wealth.
• 10) Two companies of 5 highwaymen in the street with weapons drawn, arguing about robbery rights in the local area. Villagers hide indoors.

 

Town

• 1 highwayman in jail. Mob of angry fans demand their release.
• 2 concerned citizens speaking in public about the dangers of glamorizing the highwayman way of life. Townsfolk mostly disinterested.
• 3 incognito highwaymen spying on merchant company.
• 4 elven highwaymen on decade-long break from robbery, overheard talking about their hidden treasure.
• 5 highwaymen daringly rob the party in the middle of the street (after bribing the guards). It’s mostly a publicity stunt.
• 6 highwaymen hiring porters for an extravagant clothes shopping trip.
• 7 highwaymen, the Regents of the Road, have massive bounty placed on their heads by town officials.
• 8 actors making a play about legendary highwayman “Perfect Johnny” said to operate in these parts. The script writer would love to meet him.
• 9 drunken fans debating which highwayman is the best. Brawl will begin soon.
• 10 highwaymen holding a ball at the fanciest tavern in town.