I grew up in Madison and currently live in the Twin Cities. I have a deep love for Upper Midwestern cities, especially Madison, Twin Cities, Milwaukee and Chicago and would recommend any of those cities to anyone. Yes, it's cold and snows in the winter, so if you can't handle that, you probably can't handle the Midwest in general. If you're looking for martini bars and clubs, Madison's probably not the place for you. But if you'd like farmers markets, coffee shops, laid-back bars, and lakes, it's perfect! I remember when growing up people always like to say that Madison has the most restaurants per capita than any other city in the country. Not sure if that's technically true, but if feels true. I'm a big fan of the Weary Traveler on Willy Street.