I don't like "wandering encounters," per se. What I'd much rather do is compile lists like this one, pick one that suits me to throw in for local color, and then cross it off. Likely I'll get to the end of the list in a dozen years or so.
Obsidian: An outcropping peeking through a blanket of moss, there are several hundred pounds available, in both glossy black and charcoal grey, with the occasional paler striation.
Old hut: Nobody has lived here for a while, but it has been used as an emergency shelter recently; there are a few logs of firewood, a small cache of a few pounds of smoked meat (only mildly rat-chewed), a bundle of tattered blankets on a wood frame bed, and the place has been swept and tidied. It’s solid enough for decent shelter in a heavy storm, with a bit of patching up.
Mountain Man: Old as the hills, and his language is riddled with pithy slang. His weathered packbasket is full of herbal forage and interesting colored stones. If treated with courtesy – and especially if gifted with wares or foods from the lowlands – he'll be inclined to share his encyclopedic knowledge of the area for miles in every direction, and knowledge of everyone there is to know.
Children: Here for the fun of it, collecting nuts or rocks, scavenging herbs, or just playing; their holding or hamlet is within a mile. Whatever they're doing, they'll be annoying to the PCs. If they're molested outright, they'll scream, scatter ... and the PCs will find out that at least one of them has a sling that very much is NOT a toy.
Hawk: The hawk seems to follow the party, and occasionally makes diving runs at them, without quite striking home.
Campsite: The area has a number of campfire beds and a lot of trash, as if a hundred people had camped here, and only a day or two ago; the ashes are still warm. They seem lavishly equipped, from the debris around, and are very careless with fire setting, sanitation and the concept of living lightly on the land. The trail they took is thataway ...
Bearhunter: A man snores inside a decrepit lean-to, not willing to be awoken. If he is rousted -- which he'll do if anyone approaches too closely -- he’s irascible, unwilling to deal with the party, and a vicious, deadly, veteran fighter.
Amphorae: Four large capacity (30+ gallon) stone jars are half-buried in a gully. They look old and worn, and weigh over 50 lbs apiece.
Waterlogged saddlebag: This heavy 60-lb saddlebag has broken (or severed!) straps. It contains sodden tradegoods -- with current tax and tariff seals -- some waterlogged clothing, and water-damaged letters.
Odd dirt: The soil along this stretch is colored differently, strikingly so, than the prevailing soil in the region.
Serpents: Three large snakes sun themselves on a large, flat rock that’s underneath a break in the canopy. While they’re venomous, they’re not aggressive, and will flee into the underbrush if approached.
Pillar: On a rocky outcropping is a tall, weathered marble pillar, 30' tall and with a flaring pedestal at the pinnacle. It is carved in runes from a dead language, in the style of a bygone age. Just getting out to the base, on the outcropping, is a technical climb of moderate difficulty, and it’s exposed to the weather.
Statue: A weathered stone statue is set in a dell on the hillside. The statue is well preserved considering its antiquity, but is greenish from the moss and algae in the area. Locals like to leave flowers and gifts of fruits and nuts on it, believe it to depict a regionally worshiped deity, and will freak out if it's molested or in any way disrespected.
Sorrow: The still figure of a beautiful, auburn-haired woman, freshly killed by a deadfall that broke her back, is fallen couple dozen yards upstream from which the party was drinking, bathing or fording, just moments before – the water pooling around her.
Skinning knife: An uncommon knife made by local hunters, sporting a twelve-inch blade (which seems to have been salvaged from long-ago blademasters’ work), of fine craftsmanship, the haft and sheath made of polished bear bone. It can't have been lost long; the edge is keen enough for shaving.
Leviathan: The skeleton of an unidentifiable creature of impressive size is calcifying, stretched across the mountainside. Its fangs alone are the length of swordblades.
Bathers: Near a calm mountain pool, a group of naked bathers either wave, and invite the PCs to swim with them with suggestive comments ... or stare and cover themselves in embarrassment, whatever the opposite of the party’s prevailing mores suggest. (The water, if PCs indulge, is icy cold; the locals are used to it.)
Forester: A woman appointed by the Crown to patrol for poachers and enforce the Game Laws; the territory is either beyond the scope of the local noble, or the noble is opposed to her actions, and eager for her to be taken down a peg. She is an expert in the ways of the high reaches, and greatly knowledgeable – if not “book smart” – about natural philosophy. That being said, the locals have no use for her, and will give the cold shoulder to PCs obviously friendly to her.
Black pool: A natural crude oil release leaves a sticky, warm, viscous residue.
Shield: This steel shield (fashioned in the style of a bygone age) is weathered, but the heraldry is still visible – though even a trained lowland herald couldn’t recognize it. It's tarnished, but not rusty, which given the environment is flatly impossible.
Will O’The Wisp: Just after sunset, the PCs see dancing lights on a misted ridgeline.
Cultists: A clutch of Shub-Niggurath cultists pray in the thicket. They do not take kindly to having their ritual interrupted. Before turning irrevocably and implacably hostile, the cultists will demand (once only) that the party convert to their ways, and allow the Dark Deity’s holy soil to cover their bodies, in submission to the will of the earth.
Gravesite: A rotting plank, crudely carved, lists the names – so far as the locals knew – of a caravan slain to the last man near here. It rests on a large barrow under which the victims were buried, and exhorts passersby to pray for their souls. (PCs seen by the locals not to do so are treated as godless, and with suspicion.)
Look sharp! A strong brisk wind coming in off the mountains. The clouds overhead are moving fast, but you can see bad weather on its way ... rolling in like an avalanche.
Fossils: Fossilized stones and shells of common sea creatures, as well as ancient imprints of fabulous creatures long extinct.
Cache: A smuggler’s cache, marked by a strip of colored cloth (or a hatchet blaze) tied to a tree, allowing the smuggler to retrieve the goods at some later date. These are either illicit, or subject to taxes the smuggler is dodging.
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