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.