A abnormally large toll booth sits on the side of the road. A well dressed troll mans the booth. Instead of asking for a toll, the troll gives each traveler 5 gold pieces and wishes them a safe journey.Igor's covered and enclosed wagon has broken down. He is hastily repairing the broken wheel as the wagon is shaking and his horses are bucking. The wagon filled with ice blocks and a recently sedated yeti has stirred from his sleep.This stretch of road is filled with leaves and branches. A dozen ankle holes have been dug throughout the trail. Anyone walking on this stretch of road must make a dexterity check to avoid twisting an ankle. A twisted ankle reduces movement by 1/4. A cure spell or 1d3 days of rest will eliminate the penalty.You hear a voice in the bushes. A wife is nursing her husband who broke his leg. They are from a nearby town and are on the run from a gang of tax collectors and their goons. Her husbands debt is so much that his life is forfeit.A Gypsy caravan is parked on the side of the trail. A smattering of tents and wagons fill the rest stop. A group of baccae has been travelling with the Gypsies and reveling in wine and spirits. Anyone who approaches the caravan will have a baccae invite them to party with them. First refusal irritates the baccae, a second refusal sends it into a rage.You stumble upon a boulder with a vaguely humanoid face. The boulder whispers that he knows all. The boulder is actually a trapped elemental spirit who been on this road for a thousand years and extremely lonely. He has vast knowledge of everyone who has traveled this road and is willing to share knowledge in exchange for companionship. It is lonely being a rock.A greased pig is dashing down for the road in a panic. Two farmers are settling a bet on who can capture the pig the quickest. The group is invited to participate. Winner gets the finest swine in the land.. Dream Wolves stalk the road. A distant howl has been known to put travelers to sleep. A save is needed or you doze off. You awake in shadowy version of the road and terrain. Your physical and mental stats swap places as Wolves of Ethereal descend upon your location. You can't break the slumber until the wolves are dead or your sleep turns eternal.The roadside inn has a problem. It has been shrunk to 1/20th its size and its patrons are in a panic. A Witch has curse them for stealing fruit from her garden. They beg the group to parley with the Witch and negotiate an end to the curse.On the side of the road is a lemonade stand. Two dopplegangers are disguised as teenage girls. They are selling lemonade to raise coin for the local orphanage. Of course, the lemonade is poisoned.An exhausted knight returning home from a distant war. He believes he is the lone survivor of his unit and paranoid that he is being trailed.A barnacle covered galley frigate boat is overturned in the middle of the road. The boat is landlocked and many miles away from a body of water. The group can hear movement from within the boat.For more random encounters and tables of inspiration, check out my Random Encounter Index