Oh man. I love flying over the mountains!
I remember a few years ago, I was flying back home to St. Louis from Portland, OR. I was flying Southwest, where you can choose your seat. So I asked a flight attendant what side of the plane Mt. Hood would be on. She wasn't sure, so she asked the Captain (I think?) and she told me it would be on the right side of the plane. A fellow passenger behind me heard our conversation and said, "No, it won't. It will be on the left side. Here, sit behind us." So I did, and they pointed out every peak in the area as we took off, and pointed out where their home was. Turns out they were from St. Louis and they told me, "We basically moved here because of Mt. Hood." That's got to be my favorite flight story.