A Two-Hour Adventure for 4–8 Level 2 Characters
For years, merchants traveling the roads leading to Riversmeet have whispered the name Shannon “Red” Sweeney with equal parts frustration and fear. Though never a particularly dangerous swordsman, Sweeney's talent for deception, manipulation, and cowardly survival tactics has allowed him to evade justice far longer than anyone thought possible.
Now, while traveling toward Riversmeet, the adventurers find themselves the latest targets of his schemes. What begins as a simple roadside ambush soon spirals into a chase through the wilderness, a confrontation with a territorial owlbear, and an assault upon a hidden bandit stronghold.
The adventure begins approximately one day's travel from the town of Riversmeet, a small farming community of no real consequence that the party plans to stop at for the night after their last adventure.
Allow the players an opportunity to discuss their journey, establish marching order, or engage in roleplay before introducing the encounter.
When you're ready, read or paraphrase the following.
The road to Riversmeet winds through a stretch of rolling grasslands broken by occasional clusters of trees and weatherworn stone outcroppings. The afternoon sun hangs low overhead, bathing the countryside in warm golden light while a gentle breeze stirs the tall grass on either side of the trail.
For most of the day, the journey has been uneventful. The sounds of distant birds and rustling leaves accompany each step as the road bends between a series of rocky hills.
Suddenly, a crossbow bolt whistles through the air and buries itself in the dirt only a few feet ahead of the lead traveler.
Almost immediately, voices erupt from both sides of the road. Armed figures emerge from behind rocks, trees, and patches of brush, weapons drawn and leveled toward the party.
At the center of the ambushers stands a lean man wearing a weathered hat and a faded green coat. He flashes a crooked smile and casually tips his hat toward the adventurers.
"Now then," he calls. "Let's keep this pleasant. Hand over your valuables, and we can all go home happy."
The attackers consist of Sweeney and several bandits hiding throughout the surrounding terrain.
For larger groups of players, add an additional 2–4 bandits.
The roadside rocks provide half cover to creatures hiding behind them.
Several areas of brush count as difficult terrain.
An overturned merchant wagon provides cover and creates an obstacle in the center of the battlefield.
Unlike most bandit leaders, Sweeney has no interest in proving his bravery.
He avoids direct confrontation whenever possible and prefers to let his followers absorb the majority of incoming attacks.
During combat he continually shouts instructions, encouragement, and increasingly desperate threats.
If reduced below half his hit points or if most of his followers are defeated, Sweeney immediately begins searching for a way out of the situation.
If at least half the bandits have been defeated while Sweeney remains alive, he attempts to end the fight.
Read:
As another of his followers falls, Sweeney's confidence visibly crumbles. His sword lowers slightly and his eyes dart around the battlefield as though searching for some impossible escape route.
Finally, he lets out a long sigh and raises both hands.
"All right. Enough."
Taking several cautious steps backward, he offers a nervous smile.
"Clearly I've made a mistake. I've been working these roads for years and I've never met a group quite like you."
He nods respectfully.
"You've earned my respect, and that's not something I give lightly."
Any character may attempt an Insight check.
Sweeney appears frightened.
His apology seems genuine at first glance, but something about it feels forced.
The apology is entirely self-serving.
He is not remorseful. He simply wants to survive.
Sweeney's smile never reaches his eyes.
Beneath the flattery, the character can still see smoldering resentment and hatred. He has no intention of changing his ways and appears to be actively searching for an opportunity to turn the situation to his advantage.
The character gets the distinct impression that, if allowed, Sweeney would happily lead the party straight to their deaths.
Once he has secured the party's attention, Sweeney proposes a bargain.
Read:
"Now, I know what you're thinking," Sweeney says. "You're thinking poor old Sweeney deserves to spend the rest of his days rotting in a cell somewhere."
He places a hand dramatically against his chest.
"And honestly? Fair."
After a brief pause, his grin slowly returns.
"But perhaps there's another option."
He gestures vaguely toward the surrounding hills.
"I've got a stash hidden nearby. Gold, jewels, valuables collected over many years. Enough treasure to make this whole unfortunate misunderstanding worthwhile."
He takes another careful step backward.
"Let me show you where it's hidden, I’ll be on my merry way, and we'll call the matter settled."
If the party accepts Sweeney's proposal, he leads them away from the road and into the hills.
Unknown to the characters, there is no treasure.
Sweeney is leading them directly toward an owlbear den.
After roughly thirty minutes of travel, read:
The hills gradually become steeper and more rugged as Sweeney leads you through a maze of rocky trails. Eventually he stops before a dark opening in the side of a limestone cliff.
The cave mouth gapes like an open wound in the stone. A foul smell drifts from within, carrying hints of wet fur, damp earth, and something far less pleasant.
Scattered around the entrance are fragments of old bones, scraps of leather, and several pieces of broken equipment partially buried beneath dirt and leaves.
Sweeney points toward the darkness with an enthusiastic smile that feels strangely out of place.
"There it is," he says. "My secret vault."
Before entering, the party may wish to examine the area.
A character identifies several enormous tracks surrounding the cave entrance.
The tracks belong to a large beast rather than a humanoid.
The tracks resemble those of a bear, though they possess unusual avian characteristics.
Several of the bones scattered around the entrance appear relatively fresh.
Whatever made them likely still lives nearby.
Sweeney is trying very hard to appear relaxed.
His constant encouragement to enter first is highly suspicious.
Should the adventurers accuse Sweeney of deception, he immediately attempts to talk his way out of trouble.
"What? Me? Deceive honest adventurers? I'm wounded."
"Look, every treasure vault needs security, doesn't it? That's just good business."
If the party continues pressing him, he becomes visibly nervous.
At the first sign of violence, Sweeney attempts to flee.
Unless physically restrained, he dashes into the surrounding hills and begins making his way toward his actual hideout.
The cave consists of three chambers connected by winding natural tunnels.
The interior is dark unless the party brings a light source.
The smell becomes stronger the deeper the party ventures.
Dripping water echoes throughout the tunnels, occasionally creating sounds that resemble distant growls.
The first chamber serves as a warning to anything foolish enough to venture deeper.
Read:
The tunnel widens into a broad cavern littered with bones. Hundreds of fragments crunch beneath your feet as you move through the chamber. Most belong to deer, boars, and other woodland animals, though several humanoid skeletons can also be spotted among the remains.
Claw marks score the stone walls, and long fur clings to rough surfaces throughout the room. The air feels heavy here, and every sound seems unnaturally loud against the otherwise oppressive silence.
At the far end of the chamber, a narrow passage continues deeper into the cave.
A character who spends several minutes searching may make an Investigation check.
The character uncovers:
The character also discovers:
Characters examining the chamber may make a Nature check.
The creature living here is likely territorial rather than predatory.
The bones suggest it regularly hunts animals and only occasionally attacks people.
This information may prove useful later when deciding how to handle the encounter.
A narrow winding passage connects the outer chamber to the heart of the den.
Read:
The tunnel narrows considerably, forcing you to move single file in some places. Deep gouges have been carved into the stone walls by enormous claws. In several places, the rock itself has been cracked or splintered by repeated impacts.
The smell of animal musk grows stronger with each step. Somewhere ahead, you hear a low rumbling sound that might be distant breathing.
The final cavern serves as the owlbear's lair.
Read:
The tunnel opens into an enormous natural chamber whose ceiling disappears into darkness overhead. A shaft of sunlight filters through a crack high above, illuminating a massive nest constructed from branches, fur, leaves, and scavenged debris.
Animal carcasses lie scattered around the room, some fresh and some long since reduced to bones. Broken wagons, torn backpacks, rusted weapons, and other remnants of unfortunate travelers are partially incorporated into the nest's structure.
For a brief moment, everything appears still.
Then a deep, resonant growl rolls through the cavern.
A massive shape rises from the far side of the nest.
Feathers bristle.
Talons scrape against stone.
Two enormous amber eyes lock onto the intruders.
The owlbear has noticed you.
Use the standard Owlbear stat block.
The owlbear behaves like a territorial animal rather than a tactical monster.
It:
If reduced below one-third of its hit points, the owlbear attempts to retreat toward the nest and defend itself rather than continuing an all-out assault.
Observant players may realize the creature is protecting its territory.
Characters may attempt to avoid combat.
The character successfully communicates that the party is backing away.
The owlbear allows them to retreat without attacking.
Throwing fresh rations or animal meat grants advantage on this check.
Creative roleplay should be rewarded.
After defeating or bypassing the owlbear, the party may search the nest.
Read:
Upon closer inspection, the nest contains far more than sticks and animal remains. Years of scavenged objects have accumulated beneath the outer layers, creating a surprisingly valuable collection of lost belongings gathered from countless unfortunate travelers.
Searching the nest reveals:
A character discovers a locked strongbox partially buried beneath the nest.
Inside:
While the party explores the cave or battles the owlbear, Sweeney attempts to flee.
Unless a character specifically remains behind to watch him, he escapes automatically.
When the party eventually exits the cave, read:
The hillside outside is silent.
Sweeney is gone.
Only a handful of footprints remain in the dirt, leading away from the cave and disappearing into the wilderness beyond.
Whatever gratitude he claimed to feel, it clearly wasn't enough to stick around.
Whether Sweeney escaped during the confusion surrounding the owlbear encounter or fled after the roadside ambush, the adventurers are left with a choice. They can continue their journey toward Riversmeet and leave the bandit to whatever fate awaits him, or they can finish what they started and ensure that Sweeney never threatens another traveler.
If the party chooses pursuit, they quickly discover that the highwayman is far from the master criminal he pretends to be. While Sweeney possesses a talent for deception and self-preservation, panic has a way of unraveling even the most carefully laid plans. The trail he leaves behind is hurried, sloppy, and increasingly desperate.
As the sun begins its descent toward the horizon, the hunt is on.
Read or paraphrase the following:
The cool evening air feels refreshing as you emerge from the darkness of the owlbear's den. The sun has begun its slow descent toward the horizon, painting the surrounding hills in shades of gold and orange. For a few moments, the wilderness is quiet save for the distant chirping of insects and the rustling of grass in the breeze.
It quickly becomes apparent that something is missing.
Sweeney is nowhere to be seen.
The highwayman has taken full advantage of the confusion surrounding the owlbear encounter. Near the cave entrance, a series of hurried footprints cut through the dirt before disappearing into the surrounding hills. Judging by the depth and spacing of the tracks, he left in a considerable hurry and has no intention of waiting around to see whether the party survived.
Rather than tracking Sweeney to a sprawling hideout, the final act of the adventure focuses on a tense pursuit through the wilderness before darkness falls.
Run this as a skill challenge requiring 5 successes before 3 failures.
Allow players to describe how they contribute to the pursuit. Encourage creativity and reward clever ideas with advantage where appropriate.
Suggested skills include:
No skill should be used twice in a row.
Read:
The trail winds away from the cave and into increasingly rugged terrain. The rolling hills become steeper and more uneven, forcing you to navigate rocky slopes, narrow animal paths, and patches of dense brush. Though Sweeney's trail is far from subtle, it is clear that he knows the region well and is taking advantage of every shortcut available to him.
As the afternoon wears on, the shadows grow longer. Darkness is still several hours away, but not by much. If Sweeney reaches whatever refuge he has hidden in these hills before nightfall, tracking him afterward could become significantly more difficult.
For the first time since the ambush, the advantage belongs to neither side. The outcome now depends entirely upon who can move faster.
Read:
The signs become easier to follow as the pursuit continues. Broken branches, disturbed patches of grass, and occasional footprints reveal that Sweeney is no longer taking the time to conceal his movements. Whatever confidence he displayed earlier has evaporated.
The trail suggests a man who is no longer executing a clever plan but simply running as quickly as he can. For the first time, it seems possible that the infamous highwayman is genuinely afraid.
Read:
As you crest a rocky rise, fresh evidence of Sweeney's flight becomes impossible to miss. A discarded waterskin lies abandoned beside the trail, while a short distance farther on rests a small sack containing a few scattered personal belongings. It appears he has begun shedding anything that might slow him down.
The tracks ahead remain fresh and clearly defined. Judging by the condition of the trail, you cannot be more than a few minutes behind him now. If you continue pressing forward, there is a very real chance that you will catch him before he reaches safety.
Whenever the party accumulates a failure, introduce one of the following obstacles:
Loose Scree. A steep hillside partially collapses beneath the party's feet, forcing them to navigate unstable terrain.
Thorn Thicket. Dense brambles block the quickest route forward and slow the pursuit.
False Trail. Sweeney doubles back and attempts one final trick, briefly leading the party in the wrong direction.
If the party reaches five successes before three failures, read:
The trail eventually leads to the top of a low ridge overlooking a secluded valley nestled between several rocky hills. Hidden among a cluster of trees near the valley floor sits a small campsite. A modest canvas shelter has been erected beside a dying campfire, while several supply crates and a saddled horse stand ready nearby.
As you emerge onto the ridge, a lone figure turns toward the sound of your approach.
Sweeney freezes.
For several long moments, nobody moves. His eyes flick from one adventurer to another before briefly settling on the horse waiting only a few feet away. The expression that follows is not anger or defiance, but pure disbelief.
Slowly, he closes his eyes and lets out a long, defeated sigh.
"You have got to be kidding me."
If the party accumulates three failures before reaching five successes, read:
By the time you finally locate the trail's destination, the last traces of daylight have nearly vanished from the sky. The campsite sits abandoned beneath the growing darkness, illuminated only by the faint glow of dying embers.
A weathered bedroll remains beneath a simple canvas shelter, while several crates of supplies sit undisturbed nearby. Judging by the state of the camp, its owner left in a tremendous hurry.
Fresh tracks leading away from the site confirm your suspicions. Sweeney escaped less than an hour ago.
Though the highwayman himself has slipped through your fingers, he clearly left behind far more evidence than he intended.
Whether Sweeney is present or not, the campsite can be searched.
Read:
The campsite is surprisingly modest for a man who spent years cultivating the reputation of a notorious outlaw. Rather than piles of stolen treasure, the camp contains practical supplies intended for long-term survival. A canvas shelter stretched between two trees provides protection from the elements, while a small cooking fire smolders within a circle of stones.
Several crates contain preserved food, spare clothing, and travel equipment. Everything about the site suggests preparation for a quick departure rather than a permanent home. It is less the hideout of a criminal mastermind and more the emergency refuge of a man who has spent years expecting to run.
Searching the camp reveals:
If the party catches Sweeney, allow one final roleplaying scene before combat begins.
Read:
Sweeney stands beside the campfire with one hand resting nervously on the pommel of his sword. The familiar crooked smile remains plastered across his face, but it now appears more like a shield than a genuine expression. For the first time since meeting him, the illusion of confidence seems thoroughly exhausted.
His eyes briefly drift toward the waiting horse before returning to the party. The calculation is obvious. He is measuring distances, considering possibilities, and searching for an escape route he already knows does not exist.
After several moments of silence, he gives a short, bitter laugh and shakes his head.
"You know," he says, "most people would've taken the treasure and gone home by now."
He pauses thoughtfully before adding, "Actually, there wasn't any treasure, but you get the idea."
Despite the joke, there is little humor left in his voice. For perhaps the first time in his life, Sweeney appears to have run out of tricks.
The party may choose to fight, arrest, intimidate, or negotiate with Sweeney. If combat breaks out, use the Bandit Captain stat block as well as 2-3 Loyal Bandits who were waiting, hidden in the nearby tents to see what would happen. Sweeney attempts to surrender again if reduced below half his hit points.
Read:
The sun finally slips below the horizon as you resume your journey toward Riversmeet. The hills behind you gradually disappear into the growing darkness, carrying with them the final remnants of Sweeney's long career as a highwayman.
Whether bound for justice, left behind in defeat, or escaped into obscurity, his influence over these roads has come to an end. Merchants, pilgrims, and travelers who pass through this region in the coming months will never know how close they came to another ambush, another robbery, or another one of Sweeney's schemes.
Ahead, the distant lights of Riversmeet begin to appear against the evening sky. The road stretches onward, carrying you toward new adventures and new challenges, while the story of the highwayman finally fades into memory.
Creature Reference