I know RPG's have random encounters, but in my experience, Skyrim has perhaps the "MOST random" of random encounters and I've ever experienced in the series, if that makes sense. Because of that, I'd like to ask what your most random encounters were.
-Two Companions vs The Thalmor and a Dragon
[spoiler] In the post-mainline Companions quest, The Totems of Hircine (first part) with Aela the Huntress, after I picked up the first Totem and left the dungeon. A group of Thalmor Justicars were just running head on to kill me (Aela likely would have been next if she wasn't Essential) in retaliation for my numerous actions against them prior to joining The Companions (such as randomly attacking Thalmor patrols, stopping them at the College of Winterhold, helping Delphine investigate the Embassy, etc). After we won... a Dragon attacks (and even then, I still won).
I consider the Thalmor attack sort of weird in a sense that they don't have a reason to be going after The Companions, but knowing what they did at Winterhold, I wouldn't put it past them if they did become an eventual target somehow. [/spoiler]
-Werebears following me into an inn (Dragonborn DLC)
[spoiler] This happened to me while I was taking a sort of alternate route back to Raven Rock on Solstheim. I had Serana (Dawnguard DLC) at the time and I decided to sell and buy something at the Retching Netch. Suddenly at the front door after I talked to the bar keeper, Werebears came in through the front door. [/spoiler]
What were yours most random of the encounters you had?