Madison vs Dane county is different! I've lived in downtown Madison and village of Dane. Still work in Middleton, but live in Portage. There are a lot of passionate people here who ride, and take pride in the trails. Dane county actually has a pretty good network of trails. Would we all prefer the northwoods of WI, vs farm fields, absolutely. But when you can ride out of front door, it's really nice. Saves the lodging and travel expenses. Which add up fast!
I always hope for a couple weekends of local riding, but not so lucky every year. Like this year. A lot of taverns on the trails are very accommodating to riders. There are still some scenic trails in S. WI, but you need to know which ones they are. I've done a lot of riding in the CP area.
Indy made a good point with the lodging. I'm actually staying in Eagle River this weekend. First time ever staying in Eagle River in 20 years of taking trips up North. I've always avoided Vilas due to traffic. I'm bringing my son, and my mother. This will be my mom's first trip with us on a sled trip. Since my son is going, she wanted a place with a pool, and some areas to shop. Not too many options in Northwoods winter time, so we chose Eagle River. Normally traffic goes down once we hit March.