Another 100 Great Roadside Encounters

Roleplaying Tips Newsletter #0565

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Another 100 Great Roadside Encounters

Click here to download this list, plus 1,272 more encounter ideas.

Welcome to the second batch of entries from a contest that ran earlier this year.

Use these to inspire encounters for the next road trip the PCs take.

A burned cart rests in the center of the road. On the body of the driver (or rider) is an urgent message for one of the PCs.
The party falls in with a group traveling to a religious shrine. Eventually, the party becomes aware these are actually members of an opposing religion who plan to desecrate the shrine.
The party takes down a stag for venison, but the stag is protected. It is one of the deer kept by a group of druids and their worshipers, who begin to hunt down the party with plans for dealing with them.
A group of people stand around a burned corpse nervously looking at each other, then in the PCs’ direction. Some try to quickly leave the scene while the more brave and curious continue to wait for the PCs’ approach.
An old man in outdated-looking armor approaches the party on horseback. He accuses a PC of being a half-orc and challenges them to a fight. Closer inspection reveals some of his kit to be fake – his helm is just a bowl.
It appears travellers here have two choices. The high road (plagued by giants) or the low road (plagued by lizard men).
At the head of the valley, a dam bursts, giving the party only moments to find safety before the flood waters arrive.
A nearby summoning ritual has gone awry and a demon rampages across the road.
The road goes through a canyon bog filled with toxic, flammable gas.
Just ahead, a huge tree trunk flies across the road and crashes down on the other side. A giant dog chases after.
Two groups of pilgrims from rival faiths block the road as they engage in aggressive debate. Each side appeals to the heroes for help.
A noble, disguised as a filthy beggar, tests the party’s compassion and generosity. If they pass whatever standard he’s set, then he becomes a source of various quests that require personal sacrifice to accomplish.
Two precocious children offer to buff shields or dust boots for money. They follow PCs at a distance calling them names if rebuffed.
A tearful family of wandering merchants block the road. Their youngest son has run into the “haunted forest” and are too scared to rescue him.
A band of travelling minstrels challenge the wisest looking member of the party to a storytelling contest.
A group of nomadic vagabonds approach in brightly painted wagons. A cousin of one of the PCs travels with the nomads.The cousin wants to see the world, but the PC knows her family would want her back.
A wandering soothsayer demands a contest of will before revealing a prophecy.
A scared group of travellers huddle on a small bridge. The group explains that bandits in the woods beyond the river have stolen everything they have. As the PCs cross the bridge, they are ambushed by bandits hiding under the narrow bridge. The “scared” group are part of the bandit gang.
An impossibly tall ladder rests against the branch of a tree, its top vanishing into the low clouds.
A lost child sobs beneath an oak tree.
Two ranks of royal guard form between you and an oncoming procession, allowing the large entourage and perhaps the king himself – difficult to say with all the covered carriages – to pass by.
Two score ragged men and women file by, dirty, eyes cast down, necks chained together in a line, as a slave driver and his men drive them forth to the next city.
Eying you warily, another party of adventurers allows you wide berth as they try to make their way around you.
A man in rags walks listlessly towards you, trailing a three foot chain locked to one of his ankles. If questioned, he relates a sad tale of injustice at the hands of his soulless captors.
A beautiful woman, adorned in the robes of an enchantress, emerges from hiding near the road and implores you to lend her aid.
A mass of small birds swoop from the sky and begin murderously pecking and slashing your faces.
At least three days from anywhere, your party finds a huddle of colorful tents and wagons, with gypsies about them, observing your approach in an appraising fashion.
A structure looms above the trees as you pass. A guard tower formed of rough hewn timber breaks above the treetops.
Near the road is a mound the size of a grave, obviously of recent excavation, marked at its head by an upright stake.
Smoke starts billowing up from just over the next hill.
A necromancer uses his talents to animate animal and human corpses and forces them to perform in a roadside circus. The creepy part is townsfolk from a nearby village seem to enjoy the show a bit too much.
A damaged slaver wagon sinks swiftly into the marsh. Tethered hostages struggle frantically to escape.
The broken hull of a lost ship beckons absurdly from the forest edge.
Wayward pilgrims stand enthralled on an old church road as two epic bards have a musical duel.
Elemental storms churn ceaselessly around the battle-scared ruin of an ancient shrine.
As bandits attack, the PCs realize a friend of theirs is among the robbers.
As you get the roadside campfire going and put on the pot of beans, the party is surprised by the manifestation of a number of ghostly travellers, silently staring into the fire and attempting to warm their extended, translucent hands.
The party finds dozens of poor souls buried up to their necks in the road. So dense are these heads crowded together that should the party attempt to pass through, the heads assault their ankles and feet with bites.
A great number of frogs appear from the heavens and crash down among the party members. If examined closely, the party finds a gold piece in the belly of each frog.
A great green djinn sits dejectedly upon a rock alongside the road. When pressed or plied for favors, the djinn instead tells the party a story of his part in an ill-fated love triangle.
In a slight depression in the road, the party hears a sudden rushing noise, and looks up to see a seven foot high flash flood bearing down upon them.
The road leads through a tunnel. Halfway through, the party finds a major wall and roof collapse revealing a large passage running adjacent to the road, with flickering lights visible further in.
The road cuts through a mountainside by means of a tunnel. Partway through, an underground river has broken through to cut across the path, its strong current challenging your progress with roaring rapids in the darkness.
Uneasily, you pass a moonlit graveyard far out in the countryside. You travel in silence until a plaintive child’s wail pierces the night, coming from among the gloomy tombstones.
You travel at night under a new moon. Your party’s scout points up at the sky, where traditionally stationary constellations swirl about as if stirred by a cosmic spoon.
You traverse a darkened path through light woods, a glowing chariot appears above the trees to one side.
Golden eyes follow the party in the distance and a howl is let loose as either a warning or a beckoning.
The PCs wake up to find their campsite has been ransacked. None of their normal gear is missing but their items are strewn everywhere (perhaps an important quest item is missing). A search reveals tiny fey footprints all over the campsite, and fairy laughter is heard nearby. This side quest would involve no combat, but would be rife with traps and dangerous illusions that would cover deadly traps.
A crazy backwoods seditionist has made up his own country, with its own legal system and economy only he uses. He’s a fairly powerful hedge wizard, and demands the PCs obey his laws.
A startled and disheveled merchant approaches and warns you to be careful of the road up ahead.
He tells you a large number of locals have taken to harassing and, in some cases, robbing all who travel the new road that bypasses their town. Apparently, they are upset about the dwindling trade from people bypassing their town and have decided to take matters into their own hands.
The road becomes a crumbling spiral staircase that scales a cliff.
The road before you becomes paved with smooth, shiny cobblestones. A tremor runs the length of the road and too late you realize what you mistook for cobblestones are actually the scales of a giant serpent.
A leathery-faced farmer asks for help. He runs a successful bee farm and produces the best honey in the land…or he did.
Yesterday he purchased a new queen bee, but after gorging herself on the farmer’s existing honey overnight, the queen has grown into a giant bee and gathered the farmers’ bees into an aggressive swarm that attacks anyone in the vicinity.
A traveler warns you to turn back as a dragon has been terrorizing the local populace. Forewarned, you slip off the road and cautiously advance. It is then you find dragon tracks heading east, but strangely, after each dragon print lies a small puddle of oil.
A tree of local renown, the Old King, stands atop a nearby knoll. The ancient tree is withered and gnarled, but legend says the boon of the gods is granted to any who offer it a blood sacrifice.
You decide to camp not far from the roadside, but while setting up, a ghost rises up and tries to possess you. (If successful, the PC runs off into the night, leading the party to a cave-in that claimed the ghosts’ life, hoping the party will complete his long forgotten quest and allow his spirit to rest. If the possession fails, he beckons the party to follow. If they do not, he flies into a rage and attacks.)
A couple has chosen a small glade along the road for their wedding. However, the bride is weeping and the wedding party is frantically scouring the grassy area, for it seems the ring has been lost or maybe stolen.
A disreputable merchant has set up a road stall that sells pies. Unfortunately, the pies are made with rotten meat, and whilst the pies taste fine, all who eat them become violently ill.
Outside the entrance to a silver mine, a group of protesters wave signs and shout racial slurs about dwarves stealing human jobs. As you watch, a group of dwarves entering the mine is set upon by some of the protestors.
A young couple feverishly digs alongside the road, bickering all the while. It seems they’re after something valuable buried by the road.
Off to one side of the road you see a patch of glowing, flowering plants nobody recognizes.
The PCs encounter the corpse of a rare monster.
A traveler with the PCs slowly becomes undead.
A vampire hunter seeks to temporarily join the team, warning of the dangers of his prey. Is the hunter actually the vampire?
A military force tracks a fugitive and insists on searching the PCs’ retinue.
A small community in the middle of the hostile wilderness looks like a good place to stop. The morale there is kept high by a preacher. It is unknown what motives the preacher has.
The PCs encounter a cattle stampede. The stampede is nearby but no threat. The PCs are blamed for causing the stampede by the chasing cowboys.
The PCs come to a rough and crumbly road. The ground was disturbed recently by a bulette and the PCs may fall into an empty tunnel, an occupied tunnel (by the bulette or something taking advantage of the tunnel), or just find the road travel difficult.
Gnomes decide to test a new contraption near your camp. It’s not such a surprise on this side of the world, but this early in the morning? Time to put a crossbow bolt in a gnome’s rear side.
A thin, elderly man hands out copper pieces to every child that walks by. Turns out he is the King. A small gesture to promote his good standing with the people. People who have started to think the old king is growing soft and cold hearted.
Three types of meat hang on a spit over a campfire in a makeshift camp. You try to convince yourself that it is indeed animal and not humanoid that sits above the open flames.
A militia practices their ranging with a local catapult. For fun, a few decide to launch themselves into the lake beside the road. Looks like fun, maybe they are willing to share their new toy.
The road is lined with criminals chained to stocks, with only hands and heads poking through. A visible punishment for wrongdoers. Many of the criminals shout they are innocent. Is this land corrupt or are the laws justly doled out here?
A coven of witches march along the hill’s top path as the sun drops below the horizon.
An old witch collects herbs from the bushes along the roadside while her cat educates passersby about the dangers of herbal medicines.
A field of kites litter the sky, their strings streaming down into a valley hamlet below.
A trail of blood leads from the road to a nearby barn.
An elf of questionable morality offers free potions to all who pass through the elf woods.
A dirt dwarf crawls out from the local dump sprawling across the road. The smell is putrid.
In the distance you can hear the music and dancing of the local brothel. Home to the most beautiful ogres and bearded dwarf women in the land. Take your pick.
Footprints filled with burning flames cross your path. Fire giant?
Large, strong arms wrap around a tree beside you and rip it from the ground, roots and all.
An ogre strides from the wilderness, offering his services as guide and bodyguard on a dangerous stretch of road. If paid, he serves admirably and departs. If attacked, he signals others of his band hidden nearby and they swarm to attack.
Gnomes hold yard sale.
A travelling peddler sells curses.
A path from the road leads to a collapsed house overgrown with foliage.
A collie stands in the middle of the road, it awaits the PCs and then tries to lead them somewhere. The dog leads them to an abandoned well in the woods. Ideas for the well: It leads to a dungeon with the collie’s lost master trapped inside. Or “Timmy” is a troll using the dog to lead prey to his well.
It is dark and a commoner stands next to a wagon with a torch, yelling a woman’s name and begging her to come back. After a fight over something stupid, like when to camp for the night, she stomped off into the dark woods. The twist: his wife is a visibly obvious monster (like a giantess or centaur).
As you turn the corner, a dwarf and elf are standing over a stack of goblin corpses. They argue over the kill count. For a twist, change to a hobgoblin and orc, standing over dwarf or elf corpses.
On the side of the road an old man and woman yell at each other about who forgot to pack lunch.
A knight of a holy church and his retinue have ridden out on a holy crusade against evil and demand others who serve the cause of good to join their cause on the spot.
Many years of spilled blood at a contested crossroads has lent the road itself a dark sentience. Those who camp nearby suffer nightmares and the attacks of evil ghosts.
You pass an inn at a crossroads when a sudden blast tears away the wall.
Kobolds attack a merchant’s wagon. Two kobolds attack the door with hatchets. The door blows open and a kobold is thrown out of the wagon. A dwarf appears in the doorway, brandishing a hammer. The dwarven merchant has purchased some of the kobold tribes’ eggs, which were stolen from their lair yesterday by an opportunistic rogue. The kobolds have tracked the eggs to the wagon, killing the rogue en route a few miles away.
Ahead, on the side of the road, sits a man, apparently a farmer. In his hands is a shredded blue dress, the size of a child and he clutches it to his chest, sobbing. Behind him is the smoldering ruins of a farmhouse.
A dead horse, in full tack, lies dead in a ditch. The saddle bags are full of adventuring equipment, a few gems, a gilded goblet, and a map to what appears to be a treasure trove. Cursory examination shows signs of a struggle and drag marks leading further off the road.
A wagon ahead has overturned. It appears to have been carrying four large metal containers that are now scattered about. The driver lies dead, some wicked pustules marking his exposed skin. One of the containers looks like it might be leaking some sort of liquid.
A wizard lies slain in the road, his insane Homunculus protects his body and belongings, swearing vengeance on all who disturb the corpse.
In need of food and shelter from the elements (or from enemies), the characters come to a ruined tower full of revelling adventurers. But the Rules of the House say no one may enter until they have entertained the rabble with a rousing tale.
Two young nobles recklessly race carriages along the road, heading straight for you.

Riddleport’s Grand Finale

We just wrapped up the Riddleport campaign with a grand finale session that surprised even me, the GM.

To recap fast, the PCs were caught in a faction war within the pirate city of Riddleport. Crime lords played minions like chess pieces. However, as the characters became entangled within villainous machinations, they discovered outside powers were backing the crime lords. Drow, dragonspawn, sahuagin, duergar, githyanki and more.

Eventually, the party discovered why. 100 years ago a god was slain. Put in stasis, actually, as part of a pact between great powers to give each faction time to prepare to fill the vacancy.

Turns out the mysterious Cypher Gate in Riddleport’s harbour was a key to the process where a mortal can ascend to godhood. The eight factions bided their time, grooming the ultimate champion for Ascension and gathered their forces near the gate, jockeying for position for when the elder gods would arrive to pick a new god.

The campaign began with the PCs inheriting an inn. In the basement was an impervious door the group learned was the paladin’s holy mission to protect. In the last few sessions of the campaign, the paladin learned the door protected the still-beating heart of the fallen god.

And last time I wrote about Riddleport in Roleplaying Tips, I believe the PCs were sent on a quest to retrieve an artifact called The Black Book from the 422nd layer of the Abyss – Yeenoghu’s realm. However, they were tricked into entering a pocket dimension and had to fight their way out.

Well, it took a few sessions, but the PCs eventually made their way to the top of the tower that lay in the heart of the pocket plane. Two dead PCs later, the depleted group entered the final room. A floating energy ball shot deadly rays the PCs dodged until the ball was bashed into non-existence.

Within the ball was a Soul Gem. Without hesitation, the PCs shattered the gem, releasing the souls of the two PCs who had died in the tower plus thousands of others caught in the terrible crucible over time.

At that moment appeared The Guardian, a powerful entity that had built the tower 100 years ago and maintained it using nearby villagers also caught in the pocket dimension as fuel for the tower’s magic traps and foes.

The Guardian de-cloaked and surprised everyone, because it was none other than Syzzinar, the head of the Order of Cyphers – Riddleport’s Mage Guild – and sometimes ally and sometimes hindrance to the PCs.

It turns out Syzzinar was tasked by the gods to place the fallen god’s soul in the Soul Gem a century ago and to hide and protect the gem. So he built the tower but then manipulated the PCs into coming here to release the fallen god’s soul, thereby setting in motion the imminent arrival of the elder gods and the Ascension ceremony.

The PCs escaped the pocket dimension and continued onto the Abyss to quest for The Black Book. They hoped the book would give them an edge during new god selection.

[Sidebar] Vigor the paladin acquired an Unholy Avenger Silver Sword earlier in the campaign from a defeated githyanki captain.

By fulfilling several difficult requirements, namely besting powerful evil foes in Riddleport, Vigor managed to lift the curse. In so doing, he actually released the soul of his god, Ragathiel, who was trapped in the sword as fuel for the curse.

In appreciation for his release, Ragathiel gave his loyal servant Vigor the choice of who would be Ragathiel’s faction Champion during the Ascension ceremony. This means, if Ragathiel’s Champion ended up being chosen by the elder gods, then the paladin just won the right to pick who the new god would be! [/Sidebar]

More PCs die in the Abyss, but eventually the party finds The Black Book and returns to Riddleport with it.

However, it turns out the tower had sent the PCs back in time, and they arrived the morning of the same day they left. This gave them a free day to prepare for the Ascension Ceremony (Groundhog Day style).

The group uses their time wisely to study The Black Book and learn a secret phrase sure to give them an edge during god selection.

The time of Ascension arrives and Syzzinar appears. He instructs the PCs on how to open the door in their inn’s basement (using a prop I had handed out in session #1 the PCs had forgotten about). In the room beyond, on a crystal pedestal, beat the heart of the fallen god, Aroden, “slain” by treachery some 100 years ago.

With the fallen god’s soul released back at the tower, the PCs stab the heart until it stops, thereby granting Aroden his final rest. That’s when a powerful psychic alarm goes off through the whole of Riddleport, stunning everyone, signalling the Ascension ceremony was about to begin!

The group rushes to the Cypher Gate and runs up to the arch of it, some 250 feet above the harbour bay below. There they joined the other factions and their Champions, who were already in combat trying to sabotage each other’s chances for godhood.

An earthquake then rocks Riddleport to add to the chaos. Erupting out of the ground in the north end of the city is the tarrasque the PCs found chained in a cavern several sessions ago. The githyanki who survived the PCs’ attack figured out how to release the creature! (For, if the githyanki could not win, then no one should.)

The tarrasque stomped through the city, crushing buildings and causing mayhem. Then it spied the two storey tall fin of Xyryth, the mega shark the PCs encountered at the beginning of the campaign. A near god itself, the shark turned out to be the Champion of the sahuagin for Ascension.

But the tarrasque had other plans, and it jumped into the harbour and started wrestling with Xyryth. This caused tidal waves to further devastate Riddleport and its poor citizens.

As the massive lizard wrestled the mega shark in the harbour below, the fight continued on the Cypher Gate above. Magic roared and powerful foes reign supernatural destruction upon each other. Then the elder gods finally arrived.

Assuming the shapes of raw orbs of energy, the gods wrap a shield of protection around the area and stop the factions’ fighting. In the sullen peace that ensued, the gods took measure of the surviving Champions, including the party’s paladin as proxy for Ragathiel.

Then they announced who would ascend as the newest god…. The group was excitedly waiting for Vigor’s name to be called. And then the moment came. The energy spheres turned to look straight at Vigor and announced…

…Iggwilv as the new god!

[Sidebar] The PCs started out as minions of Rictus, a vampire crime lord. On a quest for him, they freed Iggwilv, a legendary vampire trapped within the Lost Caverns of Tsojcanth. Rictus ended up marrying Iggwilv and the couple then cast aside the PCs, their use to the vampire pair spent. [/Sidebar]

It was great seeing the faces around the table. Surprise, shock, dismay. But there was another twist in store for the party.

Because just then Iggwilv suddenly gasped and fell slowly to the ground, dead. A magic dagger lay buried in her back, and a grinning Syzzinar stood behind her.

The elder gods quickly recalculated and declared Vigor-as-proxy for Champion selection!

This next part is where the players turned tables and surprised me.

When asked who would be the new god, Vigor tells the orbs that the whole PC party would ascend as a new pantheon.

The elder gods agreed and made it so.

Session – and campaign – end.

For another hour or so, we chatted out of character about what to do next. We talked about the ending and what the next campaign would be about.

After group vote, we opted to play the new god PCs part-time, and to create a new group of 10th level PCs who would be the pantheon’s champions.

The elder gods would assign the pantheon to another plane, and the new PCs would gather there to serve their masters’ bidding.

We discussed in detail what kind of gameplay the group wanted for the next “season” of the game. Players wanted short dungeons, a bit of urban play, lots of NPC opponents, and large doses of action and adventure.

We’ll play the god PCs in an intrigue game with other gods. Their actions will influence the mortal PC group’s quests and challenges, though not entirely. So, god PCs and mortal PCs will be played in parallel, in a roughly 1:4 spotlight ratio (for every four mortal encounters, we’d play a god level encounter to further the divine plot).

All that decided, we packed up for the night. I have a new campaign to craft. The players have new high level PCs to build and figure out backstories for.

This is the first campaign this group has completed. Our previous campaigns were abandoned or derailed for various reasons. It was an awesome feeling to complete a campaign.

It took 40 sessions, 2.5 years, 7 players, 1 DM and 5 dead PCs (plus several that died but were raised).

Though it was a sandbox campaign where the PCs could do as they pleased, a strong central story emerged. There were lots of surprises for everyone throughout.

And, I finally got to see a tarrasque wrestle a 100 foot shark!

Booyah.