Of the college "towns" that I've spent significant time in, I think Madison is my favorite. Lovely setting, unpretentious Midwesternism, and the core is super walkable.
I've visited Columbia, MO many times over the years and have always enjoyed it. The core is very walkable/bikeable and active. It's an artsy, unpretentious small city.
I spent a summer in Ann Arbor 20 years ago and liked it but... 20 years ago.
I lived in Boulder for 2 years. The foothills and proximity to the mountains are nice but otherwise it was was pretty meh. Very West coast pretentious. The area around Pearl street is urbanish with some decent architecture but outside of that it feels like a suburb.
I lived in Charlottesville for over a decade. The scenery is lovely and the very small core is pleasant, but there's not much else to it. The city is horribly connected (no grid except right around the downtown mall, lots of dead ends and cul-de-sacs), automobile traffic has exploded due to sprawl, and little to no effort has been made to improve conditions for pedestrians and cyclists. Culturally it's pretty stuffy and Vinyard-Vines preppie.
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