Random encounters can accomplish a lot of things. Some groups see them as annoying obstacles. Others like them for a bit of bonus XP while the GM puts a little extra strain on their resources. But they can also give a hint of weirdness to tell your players that the world has more going on than kobolds and goblins, even at low levels.

Your traveling party takes a rest on the side of the road. Or perhaps they have struck out cross-country, across farms and fields. What do you find, besides 2d4 goblins or whatever other ho-hum combat encounter your sourcebook says?

Encounters for the Strange and Wondrous:

1. Ring of Standing Stones:

As you approach the sage, the ground hums with faint energy. Suddenly, the stones pulsate, and the sage throws herself to the ground, chanting in an unknown language. The air crackles, and a shimmering portal appears within the circle. Intrigued, you approach, only to be met with a glare from the sage. “Foolish mortals! This is no mere spectacle! The stars align, and a doorway to another realm beckons. Tread carefully, for what awaits beyond is unknown.” Will you risk stepping through the portal, or heed the sage’s cryptic warning?

2. Child and Scarecrow:

The child, pale and breathless, bursts from the cornfield, pointing frantically at the scarecrow. It looms impossibly tall, straw limbs twitching, a twisted grin carved into its pumpkin head. As you draw closer, a disembodied voice whispers from the field, “He took my eyes! He devoured my dreams!” The scarecrow remains silent, but its straw eyes seem to flicker with mischief. Can you unravel the mystery of the missing eyes and appease the vengeful spirit, or will the scarecrow claim another victim?

3. Eyeless Picnic:

The halfling family smiles warmly, offering you a slice of pie. Their eyes, though, are unsettling voids, dark and bottomless. As you hesitate, the eldest boy whispers, “We lost our eyes to the Whispering Woods, but don’t worry! The food is safe, blessed by the Forest Mother.” Will you accept their hospitality, trusting their word despite their unnerving features, or flee deeper into the woods, haunted by their hollow stares?

4. Masterless Wagon:

The mules seem content, plodding forward without complaint. The wagon is filled with strange contraptions, gears whirling, pistons clanging. A note reads, “Gone seeking the Everforge. If found, tinker within! But only if your wit is sharp and your tongue nimble.” Do you dare tamper with the unknown marvels within, risking an explosion or unlocking unimaginable power, or leave the masterless wagon to its mysterious journey?

5. Singing Shrub:

The shrub belts out a bawdy tavern song, its branches swaying in rhythm. Intrigued, you join in, your voice weaving through the melody. The shrub cheers, leaves rustling with laughter. Suddenly, a twig shoots out, snagging your necklace. “Toll for a tune, friend!” it chirps. Will you barter for your trinket with another song, risk a prickly confrontation, or leave the singing shrub to its merry solitude?

6. Deadly Dance:

The duelists’ blades flash, each movement precise and lethal. Is this a deadly rivalry or a macabre dance of respect? You’re drawn into the spectacle, mesmerized by their skill. Suddenly, a misstep. One duelist stumbles, offering you a fleeting glimpse of fear in their eyes. Will you intervene, disrupting the duel and potentially inciting their wrath, or watch as the dance reaches its inevitable conclusion?

7. Spectral Invitation:

The spectral parade shimmers past, whispers brushing against your skin. The last spirit, though, lingers. Its eyes pierce you, and a voice whispers, “Join us next year, in the Land of Forever Twilight. Your light is beckoning.” This offer of an afterlife comes unbidden. Do you embrace the unknown, accepting the invitation and passing into the spectral veil, or reject the summons, fearing the consequences of accepting?

8. Night Rainbow:

The vibrant colors defy logic, painting the night sky with impossible beauty. A nearby owl hoots, “Beware the Weaver’s Loom! Its threads spin worlds and destinies!” Is the rainbow a mere anomaly or a doorway to another plane? Do you risk unraveling the tapestry of reality by touching the light, or leave the spectacle untouched, forever haunted by its impossible nature?

9. Limericks and Trinkets:

The gnome’s stall overflows with wondrous gadgets, each humming with arcane energy. He winks at you, “A trinket for a rhyme, friend! No coin will do in this realm of whimsy.” Can you craft a clever limerick worthy of his wares, unlocking the secrets of his inventions, or will your wit fall short, leaving you empty-handed?

10. Enchanted Journey:

The lovers and their loyal companions glide effortlessly, legs frozen in mid-gallop. As you approach, the mastiff eyes you with ancient wisdom. “We seek the Fountain of Everlasting Love,” it barks telepathically. “Will you guide us, and find your own heart’s desire along the way?” Do you accept the quest, potentially finding your own soul mate on this fantastical journey, or leave the enchanted pair to their eternal gallop?


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