That would be perfect for me. My father in law lives in NW Illinois and it looks as if Dodgeville is around an hours drive from him, if not less. Some pretty good hill country in that area, not sure if this flatlander will be much good up there. If the ride is going to be in the WI, IL area, there is a rail trail that runs from Savanna, IL to Moline, IL and has both flatlands and hills. The trail is about 60-70 miles in length and runs along the Mississippi river and SR 84 for most of it's length. I rode it this year and it was a really good ride as some areas of the trial involved riding some back roads.
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HCFR Cycling Team
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2017 Colnago C-RS
2012 Colnago Ace
2010 Giant Cypress