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yeah, I'm still looking for 4 seasons just not winter for 7+ months (depending on the year). Bloomington, IN looks geographically much farther south, so if I were taking a blind guess I would estimate that winters are not as grueling or cold; that is kind of what I'm going for here.
Charlottesville may be likable but I'd never move there. I think its way too isolated, with a tiny airport, expensive flights in and out, only a few Amtrak trains passing through every day, and hours drive to any big city. (I don't count Richmond as a big city)
Too bad the cold weather is turning you off or I'd say head up to Burlington, Vermont, which would be perfect in every way.
I don't think it's THAT BAD, if you're talking about being isolated. Richmond, VA has its own airport(albeit I don't think it's like say Dulles, Charlotte, or Atlanta Hartsfield, which have international flights), and more than makes up for the lack of flight service out of Charlottesville. (I always knew C'ville was more like Lynchburg, when it came to # of flights) Plus it has regular Amtrak service inbetween New Orleans(& also Atlanta) and up to NYC(plus DC and other NE corridor cities inbetween), so I don't think it's that terrible when it comes to isolation. DC isn't too far of a drive north of C'ville, if you need a big city experience. Plus of course, Baltimore isn't too much further away.
I also like the suggestions of Asheville and Chattanooga. I actually thought about suggesting Athens(as much as I also like that city too, my uncle, aunt, and cousin live there), but was a little hesitant to, since it can get very warm there in the summer. (albeit not as bad as say, Savannah can get) But what the hell, I may as well suggest Huntsville, AL as well, since I enjoyed the vibe of that city when I traveled there many, many years ago. It's similar to the size of Athens, Chattanooga, Asheville, etc. Plus, I've always heard good things about Knoxville(home of the University of Tennessee), but I've never had an opportunity to actually visit there myself.
Finally, I like Tallahassee as well(visited it once long ago), though I worry Tally may be a bit warm for the OP's wishes in regards to the ideal climate she was looking for(not too warm, nor too cold). Well, I wish the OP luck in her search for a mid-size city she likes.
Salem, Oregon? Somewhat close in size to Madison, located in a fairly scenic area of the country, very progressive area, easy access to other interesting cities via car or train, and a good liberal arts school within the city and major universities fairly close by. It's a state capital, to boot.
I'd say just pick a college town in the Mid-Atlantic, Pacific Northwest or upper South/lower Midwest. Chapel Hill, Salem (OR), Knoxville, Bloomington, Champaign-Urbana, Charlottesville, Columbia (MO), etc...
Columbia is also a scum pit. I've heard good things about Madison, so I wouldn't recommend someone going Madison --> Columbia.
Maybe I'm biased though due to my Clemson roots.
Columbia would be a better choice than Greenville, Spartanburg, or Clemson. Those places are pretty "red", and would make most from outside of that area and point of view pretty uncomfortable. Columbia at least has some resemblance of independent thought.
To the OP:
I would definately look at say Raleigh-Durham, or Asheville, NC although it is not really much of a college town.
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