10 bandit gangs which ambush you along the road.

1. Avery's Autarkic Army

 As you walk through down the road, dozens of identically clad bandits step out of the shrubbery. They're all brandishing similar swords in similar poses. One of these is Avery, the lone bandit. The rest are magical puppets mirroring Avery's moves.

2. Brutus and Billy, the Brute Brothers

A couple of beefy blokes relax out in the open next to the road, big cudgels in their hands. If your group looks weak, they'll step into the middle of your path, and demand that you hand over your valuables. If you look tough, they'll smile and wave as you go past.

 

3. A Cloudy Encounter

There are rumors of strange thefts on the road between Castletown and Cabletopia. Some evenings, a strange thick fog rolls in, acompanied by the clanking of bells. Then three silhouettes and 6 glowing eyes are seen charging forth from the darkness. The burly silhouettes shoulder past travelers, knocking them aside. After the fog clears, these unlucky travelers  find that they're missing their satchel or waterskin or somehow their shoes.

 

4. Denny (and his devilishly deceptive traps)

The cobbled road in front of you suddenly gives way to a short section made of regular red bricks. A crude amateurishly-carved statue has been recently installed along the road-side, with a wooden chest at its feet. From here, you can just barely see a set of cables running out of the back of the chest and into a hole in the statue.

 Ah, the local shire-reeve warned you about this. And sure enough, when you look around, you see a man in wizard's robes off in the distance, poorly concealed behind a small boulder and accompanied by several bored-looking mercenaries.

The man in the robes is Denny, a former wizard's apprentice with a concerningly pulsating growth on the side of his head. The growth whispers to him in dreams, gifting him grand visions of elaborate traps. Even when his devices manage to catch a traveler unaware, he rarely walks away with a haul worth more than the cost of their construction, so it's a bit of a mystery how he's managed to operate for so long.

 

5. The Most Earnest Tax Collectors

Five shining knights in golden armor stand resolutely alongside the road,  refusing to let pass anyone who hasn't paid their taxes. These are both literal taxes - for somehow they always know - but also metaphorical taxes. 1 copper coin for each time in your life that you've lied. 1 silver coin for each time you've broken a promise. 1 gold coin for each time you've forgotten to wash your hands before supper.

Most people just take the long way around.

6. The Fabulous Fowl Festival

You're walking through the woods. Suddenly, a parade of ducklings walks out in front of you. A little gremlin wearing an elaborate outfit with hat and bowtie saunters out carrying a hoop, and starts trying to coax the ducklings to jump through it. Two more gremlins follow. One begins loudly shouting about the "Fabulous Fowl Festival", while the other begins playing some horrible music on something best described as a bagpipe built by someone who doesn't understand what sound is.

A fourth skips up from behind your group, acting like she's your friend and trying to start a conversation about "how great it would be to have snacks to go with the show". At this cue, the final two gremlins appear. One falls from a tree branch, landing face first and scattering wet corn kernels all over the road. The other rises out of her hiding place in a shallow mossy puddle, and tries to sell you a crate of water-logged loaves of bread.

The trap, you see, is that the delicious plopped corn and soggy buns are laced with a powerful sedative. If the gremlin gang's ruse works as planned, and your entire group eats the snacks on offer, then you will all wake up hours later, a dozen yards from the road, with all your coins and rations missing, and your bags filled to the brim with sour mushroom jam.

7. An unnamed gangrenous gang

A plague recently swept through this region. In a small portion of people, the disease lingers, leaving them weakened and scarred. Outcast by society, some have turned to banditry. A disorganized group of such people now threatens you with knives. It's doubtful they could succeed in combat against you, but there's desperation in their eyes.

 

8. A Horrible Surprise

Some skeletons pop out. The skeletons want to steal your skin. Spooky!

 

9. The Insane Dragon Posse

A group bandits crest the hills to either side of the road. They have crazed hair and claw-like nails. They point flaming arrows your way and bark out demands. They want your gold, every last scrap you have on you. They're afflicted with a dragon's curse. They would sooner die than leave even a single gold piece behind. They don't spend the stolen coin. They're compelled to just pile it up in a nearby cave.

10. Captain Mudflip's Jumping Fingang

You're crossing a bridge. Suddenly, a tidal wave of trout leaps out of the water, soaring and flapping over the bridge. As the fish slap into you, they try to grab hold of pocket change, necklaces, and other loose valuables. The trout are a notorious pirate gang, you see.