Coming out of High Hrothgar to go back down the mountain for the first time on my very first playthrough. While I was inside, night had fallen and the aurora was out in full force. First time I'd seen it. Granted, Skyrim is the first ES game I've ever played, and the first game I got and played when it was *new* because this time around I actually had a system where I could do that. On high settings even! Glorious! So I was always inclined to be thrilled by the graphics. But standing on the mountain looking up at the amazing, imposing structure I'd just walked out of, pondering what had just happened to me inside, with the lights filling the sky behind it... I was not prepared for that. It was awesome.
Speaking of first playthroughs, starting up the game for the first time and getting that wonderful opening sequence. Again, first time ES gamer here, so had no idea what to expect. And so I was probably as taken aback and confused as my character was, except in a good way. And then the way *that* turned out... oh my. I really was scared playing through that for the first time, and not being an RPGer at all, had very little idea what I was doing or was supposed to be doing but somehow I got through it and it was terrifying and amazing and quite a rollercoaster of experiences and emotions all stuffed into that opening tutorial which I didn't even realize was a tutorial until it was all over. Mostly I was just running for my life all the way through.

The first time I met Paarthurnax. I guess I should've put two and two and two and so on together and figured it out beforehand, but I was totally not expecting that either. And with every character I'm inclined to go back up there when the events of the "life" I'm living down below get a little too overwhelming, for no other reason than just to stand in his presence. Scripted moments of the MQ aside, for me it's the most peaceful, relaxing place in Skyrim. And I would probably marry the big lug if it were possible, I love him that much.
Taking up that drinking challenge and then, after a couple drinks, realizing that something very strange was happening... oh crap what have I gotten myself into. Then waking up and gradually realizing what a long strange trip it had been. "I sold a
what to a
what? Aw man..." I spent the entirety of that adventure running around trying to find the guy I'd been drinking with, wondering what had happened to him, thinking that he was probably in danger or had been kidnapped by bandits or necromancers and it was my fault and I had to save him. And then... surprise!
Those are just a few of my highlights so far.