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Yes, I do mean city proper. Your answer is a perfect example of why I asked the question. I understand most, but what makes Madison and Cincy great? I have never been to either, but Cincy has been on my radar, so I'd be interested to know about them.
Ann Arbor MI due to having so much to do for its size. Ithaca NY is another for a similar reason as Ann Arbor. East Lansing MI's Downtown is nice as well.
I like the Armory Square and Hanover Square areas of Downtown Syracuse due to the architecture, history and both have some restaurants, nightlife spots and shopping. Clinton Square is cool in terms of its fountain, ice rink in the winter and festivals.
Chicago, DC, Seattle, and believe it or not Downtown Columbus, OH is actually pretty nice for a city it's size.
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