My home mountain, Sugarloaf (Maine), has a great story. In fact, a great big coffee table book about it just got published last year:
The Story of Sugarloaf by John Christie.
After WWII, Amos Winter (yep, that was his name!) and a bunch of his friends, now referred to as the "Bigelow Boys" (after the mountain range in which Sugarloaf is located) were hunting down the perfect mountain and location for a few ski runs. It was a long hike back in from the main road to the base of Sugarloaf Mountain, but "this is the place!" They began cutting a trail, and for the 1949-1950 season, Sugarloaf was "born!" One trail....
The rest of the story is in the book!

Which is in my closet awaiting DH's birthday next month!
Anyway, the place has a lot of history, and that one trail is now "Winter's Way" (among 100+ others) - and it's a gnarly one up top!!
Lots of history, and the first time I ever skied there, before moving out here, they were busy celebrating their 50th birthday!!