First Stop: Grand Central
Ah yes, where S was first “spotted getting off the train at Grand Central” in the pilot episode of Gossip Girl! In that scene, she had just arrived from boarding school, to the delight of Dan and to the consternation of Blair and her posse…

In real life, Grand Central station is a busy transport hub that brings in commuters from Westchester, Putnam, and Dutchess counties in New York State, and Fairfield and New Haven counties in Connecticut.
So yeah, realistically speaking, this could definitely be a homecoming queen bee’s first stop from her New England prep school. But, why didn’t the family driver just pick her up from school? That’s one secret I’ll never tell! (Well, really because I don’t know why! Ha!)
Address: 87 E 42nd Street, NY, NY 10017

