Love random encounters, but tired of the monotony of "Ten bandits show up to rob you. Roll for Initiative."? Try throwing one of these encounters the next time your PCs get a random encounter on the road. These are meant to be strange, unexpected meetings that favor roleplay and diplomacy over combat.

NOTE - Most of these encounters just say what the party will literally experience. The DM is advised to read these beforehand and come up with some sort of explanation and resolution. Or not, if you like to keep your world mysterious and your improv sharp.

1. The party comes upon a long line of hooded figures. They move slowly, swaying side to side with their hand folded in front of them, and frequently looking skyward. If the party asks what is happening, the figures will respond that they are on a holy pilgrimage for a local deity. They will also describe miracles that they have witnessed personally, and try and convince the party to join them, at least until the next town where there is a renowned prophet who is expected to perform more miracles.
2. An old man shuffles down the road, followed a few paces back by about a dozen people eagerly watching his every move. As the party passes, the man collapses and begins convulsing, and the other travelers surge up and surround him. The party can hear through the excited whispers of the other travelers the old man chanting in Abyssal.
3. A minstrel and two flag bearers are stopped on the road up ahead, along with about a dozen soldiers. The party recognizes them as bearing the crest of a large, well-known kingdom. The minstrel will stop the party and ask them if they had considered joining the local military “for the defense of this fair land from her enemies”. If the party refuses, the soldiers will step forward and the minstrel will ask again, reminding them that all they need to do is sign this agreement that says they will serve in the future. Whatever the players do from this point, they will face consequences next time they return.
4. An overturned cart lies next to the road up ahead. As the players pass it, small rocks come flying out of various holes in the cart. The rocks are small enough that they don’t do any damage and are an annoyance at most. After a few seconds of the barrage, a young child’s voice yells out from under the cart “Give us all your stuff or we won’t stop!”
5. A flock of crows clusters around something up ahead accompanied the shouts of a young woman. As the party approaches, the crows fly off to reveal the corpse of a woman, half-decayed, clutching a stone chest. The small engravings on the chest depict a beautiful woman's face with striking red hair. A green light animates from within the chest along with the voice of the young woman, who thanks the party for scaring off the crows. The voice will deny that anything is unusual and seems unaware that it has no body and can’t move, insisting instead that she’s just tired and needs to rest for a while before continuing her journey.
6. A calico cat comes wandering down the road. It stops as the party passes and meows/hisses at them loudly. It will follow them around, constantly trying to get the party’s attention; rubbing legs, climbing in backpacks, and scratching up valuable magic items. The cat is actually another traveler who has been polymorphed, who needs to be “killed” for the spell to end.
7. A gnome saunters down the road ahead, carrying under his arm a cage with a chicken inside of it. The gnome appears to be chatting with the chicken until he notices the party, with whom he will engage in friendly conversation. The gnome will quickly turn the subject to his chicken if the party doesn’t. According to the gnome “Old Dan’l” can match any animal in the fighting ring, and if the party has any familiars he will offer to set up a fight, with betting of course.
8. An awful smell wafts up from around a bend in the road. As the party follows it, they find a large, abhorrent corpse curled up on the road; something with black blood and too many limbs. The party also notices sickening sounds of gnawing and slurping coming from the corpse as they approach. Edging around the corpse, the party finds the noise is coming from what looks like a small girl, smeared with black visceral juices, and apparently eating the corpse. If the party confronts her, she will tell them that she won’t share with anyone, no matter how hungry they say they are.
9. A loud thumping is heard from up ahead, and the party can feel the earth rumble beneath their feet. Shortly after the party spots the source, a stone giant plodding down the path. The giant is oddly dressed though, clad in bright colors and flamboyant styles. If the party gets his attention, the giant will ask if they have seen Haakon (“a very loud small one like yourself”). The giant will look despondent when the party says they haven’t but will offer to show them his talent anyway. If the party says yes, the giant will look around briefly before picking up three of the party members and start juggling them.
10. The party come across a large river, too wide and swift to swim across safely. Fortunately, just downstream there are two ferrymen right next to each other, each with their own boat and willing to take the party across. As the party approaches, the ferrymen will both enthusiastically offer their services, but shortly begin arguing with one another. After a little bit, it becomes clear the ferrymen will do almost anything to win the party over to their side, as not many travelers come this way and they are both close to penniless due to the competition.
11. As the party rounds the next bend in the road, they see a lone willow tree standing near the road ahead. As soon as the party approaches, a voice from the tree will command them to stop. The willow will then begin to shift and turn to show its face to the party. The willow treant will rigorously question the party about their goals, motivations, pasts, and appearances, showing clear disapproval for an answer that refers to using non-natural magic. Should the party tell the willow too many answers it doesn’t like, it will tell them to go back to where they came from and return once they are more attuned to nature.
12. The party hears some low growls and snarls coming from off the road up ahead. Investigating the noise leads the party to an owlbear (or some other suitable animal) caught with its leg in a hunting trap. The owlbear will growl at the party, but it clearly has been here for a while and is in a weakened state. As the party is debating what to do, a man in outlander garb appears. He looks at the party in shock for a second, but then shouts “Thieves! Get out of here, this one’s mine!”
13. A small cart, piled high with stuff, moves down the road towards the party. As the party gets closer, the cart will stop and a merchant will rush out to greet the party. He eagerly offers his wares, but most of it is worthless junk (“combination hookah and coffee maker -- also makes julienne fries”) and horribly overpriced. The merchant will do everything in his power to get the party to stay and buy something, and even if they leave he will follow them, still trying to get a sale.
14. A rhythmic, grinding, sliding sound echoes from the path ahead. Moving toward the noise, the party finds a heavily damaged stone golem dragging itself along the road. The golem has been reduced to just a single arm but is determined to move ahead. It will answer the party’s questions with single-word answers, saying it’s been “called,” but it won’t stop even while talking.
15. The sun has set, and as the party is looking for a spot to make camp, they see a lone villager walking down the road. He is carrying a large sack over his shoulder and is so preoccupied with nervously looking over his shoulder he doesn’t notice the party until they are quite close. Once the party reaches him, he will anxiously try to get through them and deflects any questions, with varying degrees of success. The party does notice that there is a foul smell coming from his sack and the villager never stops looking over his shoulder.
16. The party spots something glinting in the sunlight on the path far ahead, but can’t quite make out what it is due to the glare. As the party gets closer, they see the object is about the size of a halfling and is moving toward them slowly, but still can’t make out any details through the reflection of the sun. Once the party gets within about 50ft, the glare suddenly disappears, revealing a small, oddly shaped golem whose surface is polished to a mirror finish. Even stranger, when the party takes a look at themselves, they see that they now resemble the golem (but with their reflections in the golem unchanged). The golem is happy to talk to the party but constantly gets confused about which person it’s talking to. It also seems unaware of any of the races in the world, since it only ever sees reflections of itself.
17. The party hears the sound of someone singing up ahead, but can’t quite make out the words. Once the party gets closer, they see a brightly festooned bard skipping down the path, singing loudly to himself. After listening to a few verses, the party realizes that he is singing about them; their heroic deeds and other exploits. However, he is also singing about things that he has no right to know (a party member’s secret backstory, unsavory things the party did and tried to cover up, etc.).
18. Rounding a corner, the party finds that the narrow path has been completely blocked. A huge silver dragon is snoozing right in the middle of the path, it’s stomach clearly bloated with the dragon’s latest meal. If the dragon is woken by the party (intentionally or unintentionally), she will immediately apologize for the inconvenience, but reveals that she is too full to move.
19. Shouts come from up ahead on the road. The party runs to investigate and find themselves facing a tense standoff between two identical-looking young men. They both have their swords drawn and are slowly circling each other while a young woman clutching two small children watches nervously. One says he was returning from a business trip when he found his doppelganger leading his family away; the other says he returned early from that trip to save his family from the danger he discovered they were in.
20. As the party approaches a bend in the road, a carriage suddenly comes careening around the corner at tremendous speed. Spotting the party too late, the driver tries to swerve away but ends up losing traction and causing the carriage to topple over. Immediately after the crash, the driver gets up off the ground, draws his sword, and quickly runs to put himself between the shocked party and the downed carriage. “Stay back!” he says, “Don’t come any closer!” Between the shouts of the driver, the party can hear a multitude of whispers coming from the carriage.