Upstate New York has no shortage of escape routes—charming inns, boutique hotels, and endless Airbnb gems—and choosing one is always the hardest part. Even as a lifelong New Yorker, I’m constantly discovering new corners of the Hudson Valley. This time, I wasn’t looking for just a change of scenery; I needed to be fully engulfed by nature. City slickers will know the feeling—the kind of exhale you only get when you trade honking cars for wide, open roads. Just over two hours from Manhattan by car, we made our way to Pine Plains, a charming and ultra-scenic Hudson Valley town tucked right along the border of Dutchess and Columbia counties.