(1 of 10) Gossip Girl Goes to the HamptonsThese preppy Upper East Side guys and gals have hopped on the Jitney for a chic trip to the Hamptons. Glam shows you all the exciting action on and off the set of Gossip Girl. Blair Goes for a Bike Ride Ever the girlie girl, Blair takes her cutesy bike for a trip in the Hamptons. She looks adorable and preppy in an adorable floral frock. While she looks feminine, it's not the most practical bike-wearing ensemble.