Any ideas for a cool (and cheap) place to take a roadtrip from NYC

[sexypanda]

So I just found out that I have 7 vacation days to take off work before the end of this month and am thinking of taking a roadtrip with a friend. She's kind of broke but I have about 1K sitting around and wouldn't mind paying for some stuff (she's my ex, but we've been friend for like 5 years now). I'm in NY and she's in Philly so we're going to start from one of those locations. Any ideas?