I went to Madison for grad school and I absolutely loved the place. I also grew up in Durham, NC which OP mentions so I can compare the two. Madison was absolu

I went to Madison for grad school and I absolutely loved the place. I also grew up in Durham, NC which OP mentions so I can compare the two. Madison was absolutely beautiful and I loved the culture and the people I met. I also loved that it's very pedestrian- and bicycle-friendly. I think the downside is that it's a little bit small, dominated by the university, and not very age-diverse. If you are in your thirties and explore Madison's cultural life, most of the people you meet are going to be younger than you. As for Durham, this has changed for the better since I lived there, but what I disliked was that it felt very suburban and car-centric. There are nice bike paths and parks, but if you want to get from place A to B, then you drive, period. That said, there's been a lot of development downtown in recent years, and I think this might be changing. The overwhelming positive of Durham is its diversity -- and the near-universal appetite for culture. For example I decided to try swing dancing, and I found huge and very energetic crowds -- and the people there were of all ages and walks of life. This felt very representative -- try out anything in Durham, and you will find an incredible community doing it. The wild-card about Durham is that it's sort of laid back, and people seem to move there because they want a compromise between culture on the one hand, and nice weather and an easy-ish life on the other. I met a couple of dance teachers who were at the absolute center of the swing dance scene in San Francisco, and got burned out and moved to Durham. Listening to them made me want to move to SF, which I later did. But for many, Durham strikes a perfect balance.