Orange County, NY
I grew up in Maybrook and I'm surprised it's not in the list of places, as at one time, it was a major Railway hub of the Northeast.
Newburgh and Middletown are two of the largest cities in Orange County. My High School was in Montgomery (one post card for it) and I used to go to a church in Walden (one post card for it). West Point is probably the most famous place in Orange County. The grounds there are gorgeous, and the views from the college are spectacular.