As a nerdy, lanky, white dude who looks suburban on a new hybrid bike but has urban riding experience and can sustain a fast speed, will I survive cycling, alone, on the Capital City and Southwest Commuter trails in the southwestern area (Allied Drive area) of Madison?
While checking out my favorite city forum, these are supposed to be the really bad areas of the city, but as far as the trail goes, will I be safe remaining on the trail, or is it secluded and scary and actually the opposite is true? (For example, we have a really nice trail here in Minneapolis, but it's below street grade and cyclists riding in packs and alone are getting ambushed by packs of teens, even during the day/morning, during the week, and it's not even a "bad" area.)
While I am at it, is there anywhere in Madison that I absolutely must ride while I am there? I will have a good 8-hour chunk of time, alone, one day during the week to ride, with a few random hours here and there to ride two other days. (Distance and trail/road conditions do not matter, except I will not ride on straight, boring, rails-to-trails through corn fields, as I see Madison has a lot of those when I research via Google Maps' imagery. Uh-badgerstatetrail-hem.)
The area around the campus and the capitol is beautiful, and is where I would head for that 8 hours of alone time. You'll see lots of lanky dorks around there (I wish I was one of them some days), and you'll see lots of other riders. I can't comment on the safety in the other areas, but keep in minds it's not only the capitol but also a college town - lots of easier pickings for the bad guys. And go to the union for a beer on the lake if you can. Tell them you left your membership card at home and they'll get you the temporary card you need to buy a beer.