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Oxford Mississippi is the most perfect small town - you should visit before you make your final decision. Fly into Memphis, TN - Oxford is about an hour from the Memphis airport. The people are super friendly, great art community, shops, restaurants, lots to do with the University, Sardis Reservoir, etc..... You also may want to visit Ocean Springs, MS on the gulf coast - neat art community but not as much to do - I am not sure that you would want to live there but it is a great place to visit.
Winters in Asheville: You can have cold days, but I'm not sure if it's as cold as Pennsylvania. Just last weekend, Asheville got a foot of snow, and some surrounding areas received as much as two feet. The average high in January is 45 and the average low is 25. The temperature can fall as low as 0F, and the record low is -17F. The record high is only 99F, so the summers aren't too bad. Usually days are comfortable, only in the upper 70s or lower 80s.
that's not much, if at all, warmer than New Hope. Asheville is much higher in elevation.
I'm surprised that Shepherdstown, WV isn't on the list of 25. It's very close to Wash DC and Baltimore (the same way that New Hope is close to NYC and Phila) - Shepherdstown is very artsy and bohemian, it has an annual international film festival, and is near several other interesting scenic and historic attractions.
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