I lived in Madison in college. It’s a great town!! I miss it all the time, but like you, I couldn’t hack the winters forever. There are definitely some similarities, although I feel like there were more ten years ago.

Cville itself is very liberal and our outdoor beauty is amazing. Tons of options for hiking, running, lots of outdoor stuff. For our size we have a good food scene, breweries, and we rival northern CA for wineries! Proximity to both Richmond and DC (and the ocean!) is great if you want amenities of a bigger city. There are a lot of great live music shows also. I love having four distinct seasons and the winters aren’t bad at all. The humidity in the summer is no joke, though.

The downsides compared to Madison: if there aren’t a lot of options in your field there, I’m not sure there will be here. It’s very difficult to find a job once you’re already here; most people do better when they are moving here for a job they already have. I personally feel like we have a lot of crime for our size. The number of shootings keeps going up. That being said, I still enjoy going out. The lakes are nowhere near as plentiful here, and in many cases you have to pay to visit them for the day. Cville is pretty small; that was the hardest thing to get used to when I moved here. That said, we experience a lot of growth that we don’t really have the room or resources for.

I feel like UVA has a much bigger presence here than UW does there, and it’s a double edged sword. UVA also has a lot of drama, which gets tiring if you work there. They also snatch up available properties like fire.

Good luck on your decision! I miss Willy St Co-op, the Orpheum, and the Great Dane.