Here’s a list of Wilderness Encounters created by Xanth that I found over at the Dungeons & Goofs tumblr.

1A friendly stray dog appears, when asked to speak the dog has a lot to share
2Materializing out of thin air, a magician appears claiming one of the party members is their long lost cousin. Surely this must be a mistake?
3The sky above turns into a strange hue, birds begin flying in strange patterns in response
4Copper sign on a large oak tree warns of a dangerous beast that hunts in the area
5Strange traveling merchant appears selling exotic fish and unique magical spices. They’re desperate for loyal customers, surely this won’t be the last the party sees of them
6There is a shift in the aura, the party have crossed into a large-scale summoning circle
7A faint tune is heard, a pleasant and somewhat familiar whistling. But only half of the party can hear it
8The trees appear to be sickly, covered in an acidic substance. The source of the infection lies deeper within the woods. It is hungry
9Ruins of an abandoned town lie before you, only a few decades old. What awaits within the shadows?
10A strange marketplace is stationed near a spring, all the merchants seem to be friendly but you can’t help but feel like something suspicious is going down…
11The temperature drops to an insanely low degree almost immediately. Destroyed trees and earth lie ahead covered in ice crystals and blood
12A carriage rides toward you in the distance, the driver smiles and waves. As they pass by, a tied up body wriggles and falls out of the carriage
13Pointed plant spurs shower the party attaching to their clothes, they are difficult to remove and grow in size very rapidly
14The aroma of baked goods floods your nose, it’s rich and enticing. A colossal sized monster is baking goods in a makeshift oven near a river
15Goblins camping on a hill loudly argue about a dishonest game of cards. Looks like their betting pool is full of interesting treasure
16Forest spirits glow and awaken as the party enters their domain. The spirits offer a safe way through the forest as long as they promise not to steal any of the enchanted flowers within
17A wounded Minotaur rests against a tree slipping in and out of consciousness
18Blessed by a beautiful night, the party gaze upon a shooting star. It glows brightly, increasing with size as it makes contact with the earth itself not too far away
19Travel is pleasant until the party notices their packs seem to be lessening in weight
20Twin travelers, no more than 6 years of age, approach the party lost and scared. They refuse to let anyone open up their knapsacks
21A band of muggers attack the party, they are completely drunk and can barely hold a dagger
22It seems you’ve stumbled onto the hidden base of an Alchemist, strange abominations infused with Chromatic Orbs guard the premise
23“Huh. That’s weird, did that plant just move or was it just me?”
24While scavenging for food, you stumble upon an adorable but frightened rabbit. Every time it sneezes it changes forms, starting with Owlbear
25An abandoned grain mill provides some convenient shelter for the night. Inside the mill the party discover a complex mechanical endoskeleton, the rusted metal gears creak uneasily
26Nearby, a crowd has gathered around a clay golem without a master. The crowd watches, enchanted as the golem paints masterpieces. The paint has a strange property…
27Two Monsters are locked in combat, bloodied and breathing heavily. It seems their glorious duel is one of honor, maybe bet on a winner?
28A Dragon flies overhead holding onto a hoard of gold and treasures. A sudden change in direction causes a piece of their treasure to fall
29Dozens of fish with human legs crawl out of a lake. This school of peculiar fish seem to be on a mission
30Rock music is heard in the distance followed by bouts of cheering, strange aromas fill the air. It seems you are approaching a Music Festival
31You’ve wandered onto the premises of a camp for young Wizards. A Wizarding tournament is taking place and things get very dangerous, very fast
32A cobblestone bridge stretches across a deep ravine. An Orc guarding the bridge demands you pay the toll, fortunately it is very small. After crossing the bridge you simply cannot remember where you are or where you’re going- Oh, a hey! A bridge! (And repeat)
33A Mage stands in front of an unfinished tower. Upon seeing the party, they ask for assistance
34A few hundred feet ahead, a strange house on wheels attached to two horses is parked on the side of the road. The house is somewhat destroyed but a sign on the roof is visible, “The Legendary Vagabond’s Sensational Creature Exhibit”
35The ground below rumbles as a Monster emerges catching one of the party members in their teeth
36In the center of the forest clearing, an abandoned field of flowers sway. These strange flowers are growing out the decayed body of a Dryad
37A wild chicken jumps out of the bushes, it’s beak covered in blood. Surely this chicken is no threat, right?
38Seated beside the river shore, an ethereal creature weeps. They reveal themselves as a Demigod with daddy issues
39Hungrily, a non-traditional Chimera stalks the party. The beast is stitched together poorly
40Inside the log of a fallen tree lies a poorly concealed treasure chest full of stolen loot. I’m sure nobody will mind if we take it?
41Mysterious beasts occupy a dark hollow inside a hill, they want to play a bizarre game with promise of a grand reward
42A sleeping Cyclops presents an awkward obstacle for the party, sleeping on the path. Nothing seems to be waking them and going around them is dangerous due to the environment
43A nearby earthquake collapses the ground, revealing some glowing ore
44Rotted flora is everywhere, upon further inspection this rot spreads out for miles
45Wonderful! A village! Oh and everyone here is so nice… New mayors? Oh no, you must be mistaken! Oh, you’re certain? Well then
46Lightning strikes the ground creating a dimensional rift. Certain conditions must have been met for this to have happened. Why not investigate?
47Faint, indescribable sounds are heard from every direction. As you leave the dense foliage you discover beasts and Monsters of all types in cages. Welcome to the zoo
48Little miss spider sips on some cider, eating her curds and whey. Along came the party, all powerful and hearty who scared miss spider away… You guys should probably apologize
49A few tattered shacks sit beside the open road, nothing of interest is found within. The only thing to note is that they seem to be breathing…
50Something straight out of Monster Factory is now stalking the party. Are they friend or foe?
51A poet down on their luck bumps into the party. Did I mention they’re a Beholder? Let’s hope somebody can inspire this beast, or else
52Just outside the village a group of angsty Bards are practicing their instruments. Their music is loud and dangerous, they don’t seem to understand a thing about Bardic magic
53The coolest wizard you’ve ever seen dogsleds past your crew, spraying them with glittering ice. Did I mention it’s summer?
54Just ahead, you see a ruined castle covered in moss and vines overlooking a quiet lake
55Looks like a small creature has found its way into someone’s pack. This menace has eaten all of your rations and drank all of their booze!
56YUCK! A swarm of bugs have gotten the best of your party. Fortunately, only one of you was bitten. Unfortunately, it looks like now they’ve developed a new, very unfortunate allergy
57Blistering heat has rendered your whole party sweaty and exhausted, movement is quite difficult. I sure hope some baddies don’t show up right now
58The unluckiest member of your party has their luck turned around, they found a precious jewel lodged in the dirt. They feel inspired
59The unluckiest member of your party continues their trend of haplessness, they find a precious jewel lodged in the dirt. It whispers to them at night, haunting their dreams
60After a hearty sleep the party awaken to find that they’ve been sleeping on top of a buried tomb
61A large scale battle is taking place, bodies everywhere. Wait, this doesn’t seem to be a battlefield but a serious LARP session
62Rusted weapons have been lazily discarded into a sunken pit. As the party approaches they discover this heap of weapons is actually somebody, or something’s collection
63A drunken Necromancer attempts to impress the party by casting hazardous spells
64Arrows fire at the party from behind. Someone’s been hired to take them out
65For the past few hours you’ve felt as if someone has been watching you from afar. A Druid has been tracking your party. Outsiders are rare in this forest
66A group Merchants are completely lost. Neither of them can remember anything from their past
67Religious statues are placed haphazardly around the area, nothing is out of the ordinary until the sun goes down
68Dozens of animated skeletons are exercising and doing some really intense yoga
69Beside a babbling brook, a young cow drinks alone. They’re irresistibly adorable
70An uneventful day of travel, the weather is calm the trees are- THUD! WHAT THE- The party leader has bumped into something invisible
71All metal objects are intensely pulled toward an unknown source. Steel weapons and armor don’t stand a chance
72It appears resting on that rock was quite the mistake. The stone rumbles and animates, grumpy and combative
73Meditating on floating chunks of earth is a powerful looking Monk. They claim to have been awaiting the party’s arrival. The Monk issues a challenge, a test of strength
74You’ve somehow stumbled onto a delightful Toad farm. Do you think a Witch lives around here or is there just a Toad enthusiast in these parts?
75The morning sun stirs you awake to an unexpected scene. You and your friends have been tied up and kidnapped, seated in the back of a caravan. It smells oddly of pickled vegetables
76A fishing contest is being held at the lake. The grand prize is a shockingly large sum of currency
77It is a moonless night, travel is nearly impossible. As the party decide to sleep for the night, glowing is seen in the distance. When investigated the glowing creature is seemingly friendly and it attempts to guide the party through the night
78Forest fairies are holding a festival for their gods, they invite the party to join
79ACHOO! The pollen in the air is really strong… Wait… Are those trees growing or are we shrinking? Of course we’re shrinking! Why wouldn’t we be shrinking!?
80In order to pass through this forest unharmed you must answer the goddess’s riddle. Unfortunately for the party she speaks a dead language, they hear only strange whispers
81A group of Goblins attack! After giving them a good licking you run into them again. And again… And again. Maybe we should just make peace with these dorks
82Introduce the most ridiculous NPC and have them stuck in some quicksand. Really let their character shine through, whether they are stupidly entertaining or horribly unbearable
83A strange light glows in the distance on top of a mountain. Is this a sign of good fortune or something much more sinister?
84A lone child plays the flute in the forest, they appear almost ethereal. It is a haunting melody
85Shattered Gargoyles sit in an overgrown garden, a treasure chest lies among the rubble
86Pick your favorite Cryptid and make them canonical to your world. Have the beast stalk the party for mysterious cryptic reasons. And yes, the Loch Ness Monster is an excellent choice
87The forest clearing leads to a crystal clear freshwater lake. In the depths of the water something terrifying is waiting to be discovered
88Two hyper intelligent, talking rabbits stop the party in their tracks. All they request are some books to read
89A tree, twice as tall as the others appears to be growing… Weapons? (All of those are cursed, of course)
90Next to the road, a group of Archaeologists are taking dirt samples. They’re convinced they will find some buried artifacts in the area. They are willing to pay a ridiculous sum of money if you give them some assistance, just as long as you keep this whole thing to yourselves
91Resting through the night was very pleasant for the party leader. When they attempt to greet their comrades, they have found themselves in a bed a long ways away from their resting point
92Dried up lake beds and decaying trees among a field of animal bones. You have reached the outside of a Necromancer’s circle
93Orcs with a sense of humor attempt to prank the party. Their prank is perfectly harmless, it involves just a little bit of bottled unicorn piss
94Travel is impossible on this moonless night. Unfortunately, sleeping until morning does not solve the situation, nighttime persists indefinitely
95A colorful formation on the side of the mountain piques your interest. Inside lies the abandoned home of a giant and it is full of unique treasure. Let’s just hope something else hasn’t taken residence within the forgotten halls
96Tons of bubblegum covers the roads, it is awful to travel through. The source of this mishap is a young Wizard with a sweet tooth
97Crashed into the side of a plateau, a metallic construct with strange markings and glowing lights. Surely this isn’t an actual extraterrestrial?
98While foraging for food, the party find a path of mushrooms leading into a dense Fungal Forest. Rare and undiscovered fungi grow within
99The most obnoxious bard in the world joins the party at their campfire. They claim to be weak and in need of good company, offering booze to win them over. Did I mention this bard is an infamous necromancer on the run? Yeah, that might be important to know
100Have you ever heard of the Adventure Zone? Well, Taako, Magnus and Merle have suddenly found themselves into your campaign. They are completely lost