An endless stream of random encounters

Market Day
A young boy walks around the edge of a market square with a basket selling fresh eggs. He is quite vocal about the quality of his wares and that there are only a few left. In his enthusiasm to make a sale, he inadvertently steps into the path of the party, trips and falls, smashing the last of his eggs. The boy looks up at the adventures, looks at his smashed eggs and begins to cry, blubbering something about how now he won't have the money to "help ma."

It is up to the DM whether the party is just the target of the boy's grift, or he actually is an unfortunate victim of circumstance.

The Geese
Just outside of town the party finds a gaggle of geese loitering along the path, unattended. Nearby lies a basket and a shepherd's crook, implying that someone was leading the geese to market up until a short time ago. The situation looks like something sinister may have taken place.

If the party investigates, the young goose-girl responsible for the geese is found a short ways off the path, having a secret tryst with someone she shouldn't be having a tryst with. it could be a person from a different social class, or from a rival town, or from a different humanoid race. One or both of them may be betrothed to another, or have taken up religious orders that don't allow for canoodling in the woods with anyone. In any event it's complicated, and now that the party knows their secret it could either prove advantageous or complicate the party's lives.

The Herd
The party stands above a valley they need to get across in order to continue on their quest. Down in the valley, a massive herd of creatures slowly makes their way along a course perpendicular to the party's own. The creatures could be a colossal swarm of locust-like creatures, or a slow-moving herd of giant dinosaurs, or even some sort of mass-migration of humanoids. In any event, the party could either wait for the herd to pass (which will cost them time) or pass through the herd, with appropriate skill checks to avoid being devoured or trampled.

The Huntsmen
The party hears the yapping of dogs growing closer as they pass through the woods in a relatively civilized area. A small animal runs up toward the party, looking pleadingly at them before dashing into one of the party's sacks as the sounds of the dogs draws nearer.

The party has stumbled across a hunt, being carried out by a decadent group of nobles. The animal they are hunting is actually a commoner who has been polymorphed into the creature by the unscrupulous Master of the Hunt to provide the nobles with a more skilled quarry (the nobles may or may not know this, or care).

The Sandwhirl
As the party treks through the desert, they encounter a massive whirlpool of sand, nearly a mile across. If they wish, they can stand in the current of sand and "ride" it to the other side, saving them quite some travel time but requiring some skill-checks to avoid sinking into the sands and becoming trapped. The further the party gets toward the center of the swirl the faster they'll go, but the harder it will be to get out when they reach the other side. Then there's the matter of the cause of the sandwhirl, a cluster of massive purple worms performing a strange mating ritual at the center.

The Noble
The party meets a young man or woman of Nobility, seeking a worthy cause in order to earn an inheritance, impress a true love or qualify to join a military order. If the party can succeed at some skill checks they may convince the noble to join whatever cause they're pursuing. The NPC may prove to be a burden or a great help to the party, or could simply be an agent of the Big Bad sent to betray them at an inopportune time.

The Sea of Grass and Ghosts
The party must pass through a vast prairie of waving grass. Along the way they find a few ruined structures that resemble docks, or the rotted hull of an ancient boat, hinting that long ago there was a sea here. At night, the ghosts of massive prehistoric sea creatures swim through the grasses, while ghostly pirate ships sail the eerie waves of grass. The ghost ships might lead the party toward long-forgotten wrecks loaded down with booty, or a means to travel quickly across the prairies, or just a menace to overcome.

The Circle of Stone

On top of a hill lies a mysterious circle of stones, with within it a second smaller circle of even smaller stones. This strange landmark seems to be some kind of ancient calendar. Evil creatures cannot approach the circles and good-aligned rituals are more effective if performed within the circles.

The Obelisk of Conquest

A tall stone obelisk stands along the road. An ancient reminder of a conquest that happened long ago. The players may be able to decipher the inscriptions and images on each side of the obelisk, that tell in detail of a historic battle.

The Mystic Obelisk

This strange stone structure is covered in arcane symbols. When touched by the chosen one (DM's choice), the symbols light up with a bright white glow. After a deep rumble the obelisk shoots a bright beam of light into the sky, which remains activated. The beam of light can be seen from great distance. More importantly the obelisk acts as a beacon across dimensions, to help guide travelers back to this location, even if they are on a different plane of existence. Additionally, the DM could have this object be guarded by a dangerous foe, and award the players with a stat increase for activating it. Legend has it that more of these obelisks are hidden across the land, forming some kind of interdimensional network. Activating all of them could have incredible results...

The Rogue Portal

A purple swirling gateway to another dimension. This supernatural phenomenon is always on the move, leaving a trail of destruction in its wake. The Portal can be dispelled, and either leads to a different location on the same plane, or a different plane entirely.

Roll a D12 to determine the destination

1: Leads to another plane of existence, determined by the DM.
2: Leads to another nearby land location on the same plane.
3: Leads to another distant land location on the same plane.
4: Leads to another nearby location in mid air on the same plane, 30 ft. high.
5: Leads to another distant location in mid air on the same plane, 60 ft. high.
6: Leads to another nearby location underground on the same plane, 30 ft. deep.
7: Leads to another distant location underground on the same plane, 60 ft. deep.
8: Leads to another nearby location underwater on the same plane, 30 ft. deep.
9: Leads to another distant location underwater on the same plane, 60 ft. deep.
10: Leads straight into a nearby building.
11: Leads straight into a distant building.
12: Doesn't lead anywhere. Creatures simply exit on the other side of the portal.

The Forsaken Library

The players stumble upon the ruins of a great ancient library. Most of the building is overgrown with plants and covered in sand. A large hole in the roof allows sunlight to fill the dusty halls. At night, the players can hear the sounds of voices from the past inside the halls of the library. Optionally, the DM may rule that some of the ghosts are not so welcoming to visitors, or that perhaps a lone ghost is actually willing to talk to the players. The players can also search the ruins for ancient scrolls, though most of the library's scrolls will have decayed a long time ago.

The Frozen Ship

Teetering on the edge of a large frozen waterfall, is an ancient great ship, that now functions as a town. The only means of reaching the ship from below, is a wooden cage that functions as an elevator, that can be lifted up to the ship. Access from above on the other hand is quite easy, because of the frozen water. Various stores, an inn, blacksmith and houses have been constructed on the four decks of the ship.

The Magic Garden

The party encounters a lone house with a garden. The house may or may not be occupied, but what is quite remarkable is the magical vegetable garden next to it. The vegetables in this garden grow to three times their normal size, and so each vegetable is the equivalent of three whole meals. Alternatively, the DM may rule that eating the vegetables also has random magical effects.

Lair of the Beast

The party stumbles upon the lair of a dangerous creature; a natural cave that smells of death. In the lair are the remains of its usual prey, and perhaps various valuables that the creature did not digest. Does the party linger to collect valuables and risk the creature coming back? Optionally the creature may have young that attack the players.

Tremors

The party is startled by a minor earthquake during their travels. The event may be a natural phenomenon, or perhaps it is caused by something supernatural that resides in the vicinity. The players can use a Survival check to determine which of the two is the case.

The Haunted Cathedral

The party encounters an old cathedral. The roof is broken and looks charred from a fire that must have happened a long time ago. It looks like it has been abandoned for a long time. The plants surrounding the cathedral are dead. Things refuse to grow here. From a distance the party may hear a bell toll, but the cathedral is silent and abandoned upon approaching it. During the day the cathedral is a silent and spooky place. But at night the events of the tragic fire repeat themselves in ghostly form. Both the fire and the people trying to escape the cathedral seem real, unless interacted with (treat this similar to a very convincing illusion). If the party believes the fire to be real, it can harm them, just like normal fire would. As people scream to escape the fast spreading fire, at some point the roof will collapse, and the ghostly memory ends. The cathedral is once again an abandoned ruin.

Desert Mummies

The party passes through a rocky valley, where various hollowed-out partitions in the wall are filled with the mummified remains of an ancient people, along with possessions they were meant to take with them into the after-life; coins, boats, vases, urns, jewelry, statuettes, weapons and armor. The valley is a cemetery, where the dead have been mummified naturally due to the dry climate. The dead sit upright, placed in natural poses. Stealing from the dead could cause the party terrible misfortune.

The Forest Guardian

In an old forest, the party encounters a large stone statue of a warrior, sculpted as if dressed in ancient armor, and armed with a very large stone sword. Flowers grow on the statue, and birds perch on it. A clay bowl in front of the statue contains various offerings, to repay it for its service. If the statue senses that nearby good or neutral creatures are in danger, it animates and helps to protect them, while fighting off any that would harm them. The Forest Guardian cannot communicate. It does not speak, nor understands any language. When the threat has passed, it will return to its original position and fall back into an eternal slumber. Alternatively, the DM may rule that the statue considers the party as intruders, and that it will defend the forest from them.

The Phantasmal Bridge

Across a foul and foggy swamp, a sturdy looking stone bridge has been built. The bridge looks strong, but this is but an illusion that is covering up the real bridge. Touching the railing may reveal it for what it really is. Upon stepping onto the bridge, nothing will happen at first. But halfway across, the players will suddenly plummet down into the swamp below. Once the illusion is broken, it is revealed that the bridge is broken, and has been for quite some time. Hungry creatures await the unlucky victims in the swamp below, ready to drag them to their death.

The Telling Tree

The party encounters a bizarre looking tree, with its branches bent in strange shapes. The tree looks as if it almost has a human face, and tiny fey creatures can often been found near it, along with lots of flowers. The tree responds to questions, and can give directions. Although it cannot speak, it will try its best to answer any questions that are asked by bending its branches and pointing. The tree can only answer questions that relate to the surrounding area, such as the location of nearby towns and outposts, or things that the tree may have overheard from travelers, or from the fey creatures.

The Cursed Bog
The party comes to a boggy marsh. It smells quite badly, but it does not seem to be that far to cross - going around would add at least an hour onto their journey. While it is a smelly bog, it is not terribly difficult to cross. However the stench cling to anyone crossing is, they have disadvantage on all Charisma ability and skill checks until they have a vigorous bath, or 72 hours have passed. Wild creatures will do their best to avoid any creature that has been in the bog (Hunting related Nature & Survival checks are also performed at disadvantage). If cornered, wild creatures will react with hostility and violence toward a creature that has been in the bog.

From my homebrew setting, when following the "King's Road" (2d10):

2 The Faerie Fiddler* (a bard cursed to appear as a frog-man for a crime against noble family's children, aligned with courts of the shadow fey)
3 Posters affixed to trees, boards, or buildings - wanted posters, postings for work, warnings of monsters, and festival announcements.
4 1d6 elven scouts acting as highwaymen targeting wealthy and nobility.
5 A humble roadside way-station with minimal accommodations run by a cheerful halfling couple who brew their own cider, are eager to find work for their many children, and relish sharing ghost tales with travelers.
6 2d4 wolves (50%) or 2d6 deer (50%).
7 Criminals trapped in crow cages and/or corpses hung from trees as a warning.
8 2d4 hobgoblin mercenaries spoiling for a fight or ale & wenches.
9 1 incredibly dumb Chaotic Neutral troll overseeing a bridge which it charges an unusual toll to cross (e.g. whiskey or cake).
10 2d4 redcoat thugs on patrol, at a checkpoint, demanding unlawful tolls, transporting captives, or hanging a “criminal.”
11 2d4 commoners (villagers, merchants, or mendicants) en route or in need of aid.
12 2d4 bandits led by a bandit captain as former soldiers turned to brigandry, targeting anyone.
13 Lone messenger riding at a gallop with an urgent message for a lord. At the DM’s discretion, the messenger may be wounded, pursued, or actually a spy or doppelganger.
14 1d4 knights on horseback (50%) or 1d4 loup de noir* disguised as knights (50%).
15 Damaged wagon. A search may turn up mundane items, survivors, or clues about what happened at the DM’s discretion.
16 Steady ominous clippity-clop of a horse’s hooves around the bend, but no horse in sight.
17 1 priest prostelyzing and offering healing to those who will listen to his parables.
18 1 commoner carrying a bundle with something hideous (e.g. talking head or mandrake root) for a witch; if interrupted, the witch sends her minions (stirges, swarms of bats, and/or wolves) to harangue the troublesome PCs.
19 A recent corpse (day). A ghost that cannot recall how it died, only that it was betrayed (night).
20 Prominent NPC noble, merchant, or champion with a full retinue of 4d6 guards or redcoat thugs, 2d4 knights, attendants, and either a priest or a mage.

On the road, the pcs encounter a halfling wagon selling the best tacos for miles around. They're expensive, but worth it!

The prisoner
A carriage with two horses passes, carrying a cage with a man in it. Two guards from a nearby town/city are carrying the prisoner to a crow's cage out on a hill. They mean for the man to die there under the hot burning sun. When the prisoner sees the players he pleads with them to set him free, offering his services if they do. The prisoner was imprisoned for the crime of sleeping with the wife of a nobleman (or some other person of influence and power), along with some other petty crimes. He is however lawful good.

The bandit camp
The players see some smoke in the distance. If they approach, they stumble upon a small camp with a group of 6 armed people who claim to be a traveling caravan of merchants, but they are in fact bandits. The players have caught them off guard, and the bandits do not want a confrontation with an armed group of capable adventurers. So they will try to lie their way out of the situation, and hide the fact that all of their merchandize is stolen. The players may notice that the bandits are a bit on edge, that they are very well armed, and that their goods are very varied and are all valuable items. Only if the players become too nosy, will they attack. Their leader is well spoken and friendly, and will try his best to not rouse any suspicion. If the players offer to accompany them, he will kindly refuse their offer, assuring them that they are quite capable to hold their own.

The injured bear
The players hear the distressed growls of a wild animal nearby. A bear is caught in a trap and heavily injured. If the players want to set the beast free, they should be carefuly in handling it, or they'll get mauled. If they are able to comfort the animal and set it free, it retreats into the forest. They earn an ally that will come to their help at a later point. Alternatively, they can wait for the hunter who set the trap, who claims this bear attacked and killed a boy. He is however mistaken (the true culprit could tie into the plot some how). The hunter will not be happy if the players tampered with his trap and demand compensation.

Alternatively, the bear may be a shapeshifting druid, and the trap may be magical in nature, preventing him from changing back.

Go no further!
Near a path, the players encounter an old sign in the forest/jungle that reads "Go no further!", and a skull has been drawn underneath the text. If the players ignore the sign and proceed, they'll notice that the path is partially washed out. The ground is sloped as if there has been a recent mud slide. The players should be careful not to loose their footing, or risk a tumble down a steep 20 ft. decline. There is an overwhelming sense of dread here. The trees and plants here are dead, and bare branches tear at their clothing. There are faint footprints leading further down the path, indicating that other travelers have taken this path before. As they proceed further, they will encounter some old items belonging to these travelers: a backpack, a shoe, a belt, an empty scabbard, a waterskin. Eventually they stumble upon a horrific graveyard; countless skeletal remains of the travelers, their arms and feet sticking out of the mud. These people didn't sink. It looks as if they were pulled into the mud while struggling in vain. While the creatures that attacked these travelers are no longer present, there is an opportunity here to have this threat make a reprise later on in the campaign.

The carcass in the tree
The players stumble upon the half-eaten remains of a deer dangling from a tree. If the players visit this location at night, they may encounter the predator that hoisted it up there, returning for another snack. Alternatively, the carcass may attract scavengers.

The resurrection ritual
A corpse of a female druid lies wrapped in cloth on top of a simple stone altar. A gathering of druids are attempting to bring her back to life. If the players disrupt the ritual, they may anger the druids. The resurrection may go wrong as well, resulting in the druid being brought back as a hostile undead. The ritual lasts for several hours, after which the druids rest to try again the next day.

Sightseeing
The players stumble upon a collosal statue carved into a cliff. The statue is big enough to have flocks of birds nesting on it. The statue resembles an important historical figure (possibly a king or some hero), portrayed in his armor and clutching a sword and shield. Names have been carved into the rocks nearby by other travelers and there are signs that people have often camped at the foot of the statue. The players earn bonus experience simply from visiting the statue. The statue can be seen from afar. If climbed, the statue provides the players with a good view of the surrounding area. This could allow the players to spot the next random encounter before it happens, and possibly avoid it. Two other sightseeing locations may be visible from the top of the statue, which can also earn the players bonus experience when visited.

Lights in the dark
At night the players can see flashes of light coming from the wilderness. The flashes are caused by a wizard teaching a girl how to cast spells. The girl has a natural talent for magic, but due to her social class is not allowed to study it. The wizard is teaching her in secret. The wizard offers to teach the players one new spell. Also, his apprentice may be a helpful ally to the party. She knows the area well and can provide them with plenty of local information.

The diviner
A diviner lives in a wooden shack in the forest, near a small pool of water. She is shunned by the locals, due to her prophecies. For the right price, she'll perform a divination for the party, for which she uses the pool of water. The players can see her vision in the water and hear sound emanating from it with a ghostly echo. If she is asked to spy on enemies of the players, and these enemies have any magical aptitude, then they may seek out the diviner and kill her.

The mapstone
The players find a large upright stone with a rudimentary map carved into it. The map is very old and will not show newer locations. The players can however use it to learn of older important locations in the area (including areas forgotten by the locals). The map also gives them advantage on any further navigation checks in the area.

Lake of remembrance
A foggy lake has about 20 rectangular basalt pillars scattered about it. Candles burn in recesses in the black pillars to remember the dead. Locals take rowingboats out onto the lake and place candles and keepsakes inside the pillars. In response, the pillars bring back visions of the dead. The visions cannot speak or answer questions in any way. The pillars were built by an ancient forgotten people. None remain who know who built them. The lake is considered a sacred location and none dare commit any acts of hostility on the lake for fear of angering the spirits of the lake. There are always some empty rowingboats near the shore and the players are very likely to meet locals who are busy lighting candles. The players can use this location to bring back a temporary vision of a deceased person they know and loved. The vision can't give them any insights or respond to them. They merely appear as they are in the player's good memories of them.

Message from a dying soldier
The party stumbles upon a dying soldier, who has an urgent message for the local ruler. He asks the players to deliver the message with his dying breath, for which they will be rewarded. Any attempts to heal the man are futile, since his injuries are too severe, he always dies. Any attempts to resurrect him are also futile, since his soul does not wish to return (he died an honorable death). They find him amidst the scene of a battle, surrounded by the corpses of his comrades. He may be the victim of a war-party, a monster, or the main villain, and his death could easily be tied into the main plot. The message is a warning to the local ruler, and is directly tied to the people responsible for the death of the soldier.

The stargazing monks
The party encounter a group of meditating monks, who are sitting on the edge of a large overlook. They are waiting for the sun to set, to gaze upon the stars and gain new insights. The leader of this congregation offers the players to rest here with them and share in their food, for he believes that is the will of the gods, and their purpose. If the players choose to rest here, he will offer to provide them with divine insight regarding one topic of their choosing. The monks will then read the stars and provide the players with information directly from the gods. In this location the players cannot be attacked, should they make camp here. Their politeness to the monk earns the players the friendship of the monks and good standing with the locals, especially if they share food and drinks with them.

The Shaman on the plateau
Smoke can be seen in the distance. Atop a large stone plateau is a friendly old man carrying a gnarled stick, decorated with bells and beads. He has made a bonfire here, while dancing around it. Climbing up to the plateau takes some effort and requires a strength (athletics) check DC 8. The shaman introduces himself as Mfundo, the Smokereader. He will read the fortune of the party and bless them with his holy ashes if they partake in his ritual. All that is required, is for each party member that wishes to partake to burn an object belonging to them in the fire. It does not need to be an object of high value, just as long as it can be burned easily. They are allowed to join in with the dancing and singing, but this is not required of them. The ritual takes about an hour of the party's time, but will bestow great fortune on them, as long as they burn an object to gain this blessing. Players who do not burn an object, will not be blessed.

Roll 1d12. The smoke will briefly assume the shape of animals below. The shaman will call out the name of the animal and explain its meaning to the party. He will then reach into the fire and grab some of the ashes, which are now cold to the touch. He will then rub the ashes of the fire on their skin (with their permission), granting them any of the following boons:

1. The Eagle: The party receives a vision of the road ahead, seeing an upcoming obstacle and/or warning. The eagle can reveal enemies that the party is unaware of, monsters that wait ahead, or a person that intends to betray them. It may also show them nearby towns and outposts and any noteworthy buildings.
2. The Cobra: The cobra is a symbol of protection, health, and aggression. The party is given immunity to poisons for 1d4 days, and is cured of any ailments. The cobra also temporarily coats the weapons of the party with a venom of the DM's choice.
3. The Bison: The bison gives haste and perseverence to the party. For 1d4 days all party members are given 5ft. of extra movement and receive advantage on any wisdom/willpower checks.
4. The Lizard: The lizard bestows endurance and resistance to the party. It hardens the skin of the party, giving them all 10 temporary hitpoints (which remain until spent), and a reduction of incoming elemental damage by 5 for as long as they have these temporary hitpoints.
5. The Crow: The crow bestows the gift of cleverness to the party. For 1d4 days they receive advantage on any intelligence checks. Further more, the crow shares a helpful bit of information with the party which will help them in the near future. The crow sees and hears all, and can share information discussed by other characters that he might have heard.
6. The Crocodile: The crocodile embodies strength and ferocity. For 1d4 days, every party member adds an extra +1 damage to their physical attacks, and they receive advantage on any strength checks.
7. The Bat: The bat embodies keen senses and reflexes. For 1d4 days the party receives advantage on dexterity checks and gains the temporary ability of echo location, allowing them to locate their enemies without having to see them, and allowing them to navigate in complete darkness without effort.
8. The Butterfly: A symbol of good fortune and protection. For 1d4 days the party receives a +2 to their armor class and they will not encounter any hostile encounters while traveling through the wilderness.
9. The Lion: Embodies great fortitude and strength. For 1d4 days the party gains advantage on any grapple checks, and advantage on constitution checks.
10. The Owl: Embodies knowledge and strength of personality. For 1d4 days the party gains advantage on any charisma checks, and the owl shares a piece of valuable knowledge from a distant past. The owl will also identify any unidentified items that the party carries with them by giving them the knowledge of what it does.
11. The Sphinx: Embodies challenges and magic. The sphinx reveals the nearby location of a powerful beast, which carries with it a valuable magic item of the DM's choice. It is up to the party whether they want to challenge this powerful foe to claim its treasure. This beast will only remain for 1 day, so delaying this fight is not an option.
12. The Dragon: The dragon bestows upon the party the gift of riches. For 1d4 days any gold rewards are doubled for the party.



The Whispering Tree
A mysterious tree in a clearing, whispers in a friendly voice for travelers to come near and eat from its fruit. The clearing is covered in beautiful flowers, but this is but an illusion. The players can use an action to examine the flowers, and upon a succesful intelligence (investigation) check DC 14, they see through the illusion. Instead of flowers, they see the hill is covered in the skeletal remains of other travelers. The players can search the remains for valuables, which is up to the DM. The fruit, when consumed, poisons the player. The type of poison is also up to the DM, but should be quite powerful. The tree is in fact not intelligent and cannot talk. The source of the whispering and the illusion is a group of a malevolent fairies living in the tree, wishing to give it nutrition. The players may be able to get the help of the fairies upon a succesful charisma (persuation) check DC 10. If the players roll exceptionally high on their persuation, the fairies may even give the players a valuable gemstone worth 20gp that they took from one of the less fortunate travelers. The fruit of the tree can be harvested for poison, but the poison and fruit only last for 3 days.