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Ideas for trip this Fall

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I've got 5 vacation days to burn and no idea where to go. Hopefully this thread can help my wife and I out.

We're looking for somewhere not too cold (a.k.a. < 40 degrees Fahrenheit) or too hot (a.k.a. >80 degrees Fahrenheit), within about 8 hours driving distance of central-southern Pennsylvania. She likes urban settings, I like the outdoors. We enjoy people-watching, architecture, music, and history. I would like to keep the budget under $250 a day including everything.

Any ideas? We're hoping to avoid Philly and NYC, as we've been there a lot and are looking for something fresh. Thanks!

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