Random encounters can happen almost anywhere in The Elder Scrolls games. The fifth in the series, Skyrim, is especially full of these unexpected occurrences. Sometimes they can take the form of ambushes by vampires, mages, or even Daedra. Though, not all involve sudden combat.
Some are merely parts of the story unfolding in front of the player. Hilarious or boring, they have a wide range. However, some are not often seen due to certain criteria not being met in most cases. There are plenty of planned random encounters that occur in towns and cities, though the ones found out in the wilderness of Tamriel are the hardest to come by as well as the most interesting.
10 Babbette's Snack
If the player has joined the Dark Brotherhood and has the Dawnguard DLC installed, there is a chance that they can see a familiar face upon the streets at night. Babette, the child vampire one meets in the Falkreath sanctuary of the infamous assassin's guild, can be found next to a corpse between sunset and sunrise. When asked what she is up to, she will greet the Dragonborn pleasantly before stating that she was just out for a snack.
9 The Drunken Dare
If one has completed the daedric quest 'A Night to Remember', there is a small chance that upon entering a new area, an argonian will approach and claim that the Dragonborn owes them 10'000 gold. If the player pays they will leave peacefully but if not they will attack, intent on retribution. This scaly citizen of the tundra was apparently dared by the player, while drunk, to break into a bandit camp and steal their leader's hat.
8 A Wizard's Flight
While traveling around the frigid shores of Solstheim, players can potentially come across an elf wizard seemingly practicing magic. Though, after a few moments of muttering, they launch themselves incredibly high into the air, only to return to the sandy beach and die from the impact. On their remains, their journal can be found. It, as one might expect, is full of the ramblings of one obsessed with attaining flight.
7 Wedding Guests
Another occurrence tied to the Dark Brotherhood questline can be encountered before the 'Bound Until Death' quest when the player will be tasked with killing Vittoria Vici, the emperor's cousin, at her own wedding. A noble couple will be on their way to the event with a bodyguard.
Though, they never make it there. After 'Bound Until Death' is completed, this same couple can be found upon one of Skyrim's many roads, however, this time they are significantly less regal in appearance. They were apparently robbed after meeting the Dragonborn the first time.
6 The Wanderer And The Wabbajack
If 'The Mind of Madness' quest has been completed and the Dragonborn has the Wabbajack staff in their possession, it is possible to bump into an elderly woman by the roadside. She will recognize the player through their dealings with the Daedric Prince Sheogorath and ask repeatedly to be hit by the staff's spell. If one agrees and unleashes the Wabbajack upon this woman, she will turn into a rabbit temporarily. Though, upon returning to her human form, she will not acknowledge the player unless attacked or pickpocketed.
5 A Big Fan
Although Balbus, a culinary enthusiast, can be found at any point in the game, there is a special dialogue option available if one has completed the quest 'Recipe for Disaster'. In this quest for the Dark Brotherhood, the Dragonborn impersonated the famous chef known as The Gourmet and at one point obtained written identification saying so. When in conversation with Balbus, the player can see this as a third option below the standard two and engage Balbus about cooking.
4 A Special Contract
Being part of the Dark Brotherhood holds many benefits in that there is access to very interesting quests and unique equipment, though there are some downsides.
If the Dragonborn DLC is installed and the player has completed the 'Served Cold' quest, it is possible to get ambushed by Morag Tong assassins while exploring Solstheim. This group of rival assassins likely wanted to take out some of their competition.
3 Roadside Meal
Sigar can be encountered near a dead body found in the wilds of Skyrim, though his dialogue will be different depending on whether or not the Dragonborn has completed the 'Taste of Death' quest. If one had partaken in eating the flesh of humans during this quest, Sigar will recognize the player and offer them "a bite" of the corpse. Though, if the player has not become a cannibal he will pretend that he was merely going to bury the body out of respect. Maybe he and Babbette will bump into each other someday.
2 The Many Thieves Of Skyrim
Thieves accosting one on the road are relatively common as far as random encounters are concerned, though how they will treat the player differs on how deep one is in the Thieves Guild main quests. If the Dragonborn happens to be wearing the Nightingale armor after completing the final leg in the questline, instead of trying to take their money, the thief will give the player a "share of the take" in the form of a few septims.
1 M'aiq The Liar
Probably the most famous of random encounters, though rarely seen, is M'aiq the Lair. This khajiit wanders around Tamriel spreading humourous misinformation and appears as an easter egg of sorts in multiple Elder Scrolls games. His first appearance was in The Elder Scrolls 3: Morrowind and he has been in every title of the series since then. He often shares his witty observations and comedic falsehoods with the player when they bump into him, though when that is can be a mystery. There's nothing that seems to correlate between all of M'aiq's sightings, so the player will just have to rely on sheer luck if they want to have a chat with this cat.