25 year old Winnie has finally taken the trip to California that she's waited for since she was a kid. Ready to watch the local skateboarders on her day of relaxation in the park, she's surprised to find herself in the middle of a King of the Road challenge. When a broad, beat-up looking man approaches her with an offer, she's not sure how she ended up in the kind of situation she used to watch on Thrasher's website and Vice TV. Will she accept this handsome skater's offer, or will Winnie bail out on living her teenage skating fantasy?