A thief is staging an escape with a crucial item or person the party needs to secure safely—and they’ve taken a dangerous road to try and throw the group off.

Background

A halfling thief (Name Suggestion: Lindel “Watermelon” Tolltaker) has managed to nab something or someone important to the party, depending on their goals, likely before the party ever managed to lay eyes on it. The thief has been on the run, and when the party spots them again, they’re on a busy road in the midst of the mountains. This encounter works best as a drop-in tool while the party travels elsewhere or while they’re in direct pursuit of the thief.

Whatever faction or powerful individual the thief stole from is absolutely furious, and is likely willing to both reward the party handsomely for retrieving the stolen goods, or attempt to punish them brutally if they choose to keep them for themselves.

Situation

However the theft comes about, this encounter assumes the party is in hot pursuit of the thief (who is traveling on foot), and the confrontation comes to a head on a busy and treacherous road. The thief is attempting to throw them off the trail by utilizing the dangerous terrain.

On the South side of the road, the hill slopes steeply up, and on the North side, the hill slopes downward from the road—moving upwards on the incline counts as Difficult Terrain (2 feet of movement for every 1 foot moved) and a creature that takes the Dash action on the slope falls prone at the end of their movement. Any creature on this slope that takes 5 or more damage in a single hit is knocked Prone.

Most of these encounters revolved around retrieving items. If a player wants to nab an item from an NPC, they may replace one attack from the Attack action with a contested Sleight of Hand check, taking the hard-to-hold item on a success.

Goals

There are 2 main parties interested in the stolen item or person:

  • The Thieves Guild, as well as the Thief, want to take it for a hefty profit, whether by selling it through a fence or ransoming the captive.
  • The Robbed faction, which can be an order of merchants (Encounter A), wizards (Encounter B), or clerics (Encounter C) want the stolen item or person returned at all costs.

Using These Encounters

What do your player characters want? What are their best and worst qualities? What goals are they pursuing? Read through a few of the examples below, then choose the encounter that best suits your situation.

  • If you have player characters who are pious or helpful, or who like to defend the weak, run Encounter C. If, on the other hand, they are greedy or uncaring, run Encounter A.
  • If you have player characters who want to obtain a powerful weapon, run Encounter B. If you have player characters who want to uphold certain vows, or to gain favor with their gods, run Encounter C.
  • If you have player characters who need information from or about a criminal element in the city, any encounter would be appropriate.
  • If the player characters are working to foil some kind of villainous plan, run Encounter B.
  • If the player characters are just looking to make a quick buck, run Encounter A.

Encounter A

In this encounter, the thief has robbed a valuable golden chalice from a powerful guild of merchants. On the dilapidated and dangerous road where the thief and party cross paths, there have been rockslides lately, and if the group isn’t careful, the chalice could easily be lost.

Setting up this Encounter

This encounter involves trying to take a valuable golden chalice (or other precious but non-magical item) back from the Thief. If you have player characters who are greedy or uncaring, then add a third faction to the fight: 6–7 bandits. The party can either try to slaughter their way through more opponents for the chalice, or try to persuade the bandits to help them in their battle.If you have player characters looking to just make a quick buck, then the chalice is worth twice as much to help them achieve their goals faster…should they succeed in securing it.

Action!

The Thief and 2–4 thugs face off with the party on the road. On Initiative Count 20, losing ties, a rockslide begins (and sustains itself on the same initiative count on subsequent turns). All creatures on the ground (not on a cart or other solid, elevated surface) must succeed on a DC 13 Dexterity saving throw or fall prone and be moved 15 feet North. Creatures on the hill have Disadvantage on this save.

The chalice is hard to grasp and easily lost—any creature that fails this save while holding it drops the chalice and it is dragged away by the rocks, only to be discovered with a successful DC 15 Perception check. If the chalice is not found within 3 rounds of being lost, it’s buried under the rubble and lost for good, or until a larger and better-equipped search party can find it.

Resolving this Encounter

When this encounter finishes, your players who are greedy or uncaring will hopefully have the chalice in hand. If they’re greedy and brave enough, they can try to sell it themselves instead of bringing it back to the merchants.If your players wanted to make a quick buck, congrats! They’re holding a valuable chalice.

Encounter B

In this encounter, the thief has robbed a small order of wizards of their chief experiment: a dragon egg. Unfortunately, this road is an extremely busy route for fast-moving carts, and one wrong move could easily shatter the egg or the bones of one of the combatants.

Setting up this Encounter

This encounter involves securing a fragile dragon egg while carts speed around on the road. If the party wants to obtain a powerful weapon, this egg is due to hatch soon, and the draconic magic is already starting to manifest. Any creature holding it (including the thief, when this encounter first begins) can use a bonus action to blast fire around them, dealing 1d4 fire damage to all creatures within 5 feet. After the battle ends, this ability fades as the egg grows extremely close to hatching…If the group is looking to foil some kind of villainous plan, then the Thief is a dragon cultist. They gain resistance to fire damage and a flying speed of 30 feet as draconic wings unfurl from under their cloak.

Action!

The struggle takes place on a busy road—horse-drawn carts race from East to West at top speed, undeterred by any possible collisions as they race from likely illegal activities. The Thief and 5 to 6 kobolds face off against the party.

On Initiative Count 20, losing ties, a cart careens down the road. Any creature on the path must succeed on a DC 13 Dexterity saving throw or take 1d8 Bludgeoning damage and be knocked Prone. 

If a creature holding the egg falls Prone, the egg is cracked. If the egg is cracked twice, it breaks. If you wish to go easier on your players or if they’re falling a concerning amount, raise the number of cracks to 3 or 4.

Resolving this Encounter

Player characters who want to obtain a powerful weapon may soon have a baby dragon if all goes well. While it might not be strong yet, dragons can grow quickly when they’re fed well. Just make sure it doesn’t turn on its owners…Player characters who want to foil some kind of villainous plan succeed even if the egg breaks, so long as the Thief doesn’t get away with it. Whatever faction or villain hired this thief—perhaps a dragon?—is likely furious and will single out the party for revenge.

Encounter C

In this encounter, the thief has robbed a holy order of their elderly bishop. The road here is covered in patches of sickly mold, and any creature that steps on them will inhale the deadly poison—should the old bishop take a lungful, he’ll likely die.

Setting up this Encounter

This encounter involves keeping an elderly bishop safe from inhaling poisonous gas. If your player characters are pious or helpful, or who like to defend the weak, describe the bishop as an exceedingly frail old man. His Constitution is 8 instead of 10 (-1).Otherwise, such as if the PCs uphold certain vows, or to gain favor with their gods, the bishop is associated with a god one or more of them worship, and the party may owe certain favors or promises to the church he hails from.

Action!

The bishop is held at knifepoint by the Thief and 4–6 bandits. He’ll accept a hefty bargain in exchange for his captive.

Before the battle, choose six 5 by 5 foot squares on the bridge, none of which are touching one another. These are patches of ancient mold (which are easily visible), and any creature that steps on one must succeed on a DC 12 Constitution saving throw or be Poisoned until the end of their next turn and take 1d4+2 poison damage. Regardless of the save’s result, a patch of mold is destroyed after being stepped on.

Resolving this Encounter

For player characters who are pious or helpful, or who like to defend the weak, are rewarded by the bishop for their help. The casting of a powerful spell like Greater Restoration, or the promise of rest and sanctuary in his cathedral, may be an appropriate reward.Parties who uphold certain vows, or to gain favor with their gods, are rewarded by the church. This could take the form of a holy item, a favor the faction can provide, or information the party hasn’t had access to yet. At the very least, it earns a good portion of goodwill.