I have a little story to share with you.
So I was going about my business on my Mage profile, and happened to be near the end of the Mage's Guild questline. This happened just after Archano took over the mages guild. I went down to winterhold to kill the 10 anomalies that spawned there, and there had the most random ass battle I have ever had in Skyrim.
I summoned my two Daedra lords, and went to battle along with the two mages that accompany you for backup. It was then that I noticed more than just my two allies and screaming dremora in the fight. A random person from town was stuck outside, fighting the anomalies. Durak, from the Dawnguard was fighting the anomalies. A courier was fighting the anomalies. A random wizard challenger was fighting the anomalies. The guards were fighting master vampires and death hounds.
Pure random chaos. I didn't want to use any spells other than my summons and healing for confirmed allies.
So I watched. And it was beautiful. I wish I were one of those random Russians with a recorder running it all the time to catch random stuff. When the battle was finally over, the town citizen and guards had been resurrected several times by several different groups. One of my Dremora went after the vampires and went on a beheading spree, the other went after the anomalies. Durak got ganged up on by death hounds and anomalies.
When all that was over, the challenger challenged me to a duel, while the courier delivered mail to me in the middle of the fight. Durak then decided it was also a good time to talk to me about vampires as I stood still getting shock spammed. My one surviving dremora did all the work and then promptly went back off to oblivion.
I sauntered off to Labyrinthian after going through massive piles of corpses for loot.
So, tell me fellow Skyrim bretheren, what interesting, random battles have you ever gotten into?
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I went to the College of Winterhold to buy some new spells, when I hear this roar. I look up, and I see a dragon passing on ahead, then I hear another one, and then shit got real. Pretty much every resident of the college happened to be outside, even Savos Aren. Needless to say it was an epic, but incredibly short, battle. The dragons didn't last two seconds with all the atronachs attacking them.