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I live in Madison, on the West Side, and regularly ride many of the roads you're considering. The county roads between Madison, Spring Green, Viroqua, LaCrosse provide some of the best riding in the country.
I agree with everyone here regarding Hwy 14. It's a dangerous road to be on for longer than a few miles, IMO. There are rumble strips before the shoulder in some limited stretches, but for the most part it's a 2-lane 55 mph speed limit major highway that nearly everyone goes 70 mph+ on. There's been a few distracted driver accidents out there this year too which reinforces my wish to avoid it.
I'd have no problem running 25's on paths like the Military Ridge trail. Those paths are maintained such that you can have a less than ideal setup and be totally fine. I think the only time you'd require a wide tire out there is if the trail is waterlogged.
PM me if you would like assistance building routes through the area. I'd be happy to help.
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