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I am looking for a destination that is <5 hour drive from Chicago and is a good biking destination. I want to stay in a cheap hotel and go on a few rides between 40-80 miles each day (3-4 days). Proximity to beaches, breweries and/or backpacking are a major +.

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West and SW of Madison WI is pretty nice riding. Microbreweries at New Glarus and Middleton, probably some others.

While I have yet to ride there myself, the exact same things can probably be said about SW Michigan. You can probably find some good routes around Three Oaks, MI (where the Apple Cider Century is held). Plenty of camping options can be found at the Warren Dunes State Park as well.

Depending on your location, this is about a 5hr drive: 400 Trail, Elroy-Sparta Trail, LaCrosse River Trail and Great River Trail. It's about 101 miles from the beginning of the 400 Trail to the end of the Great River Trail. Several small towns with restaurants, bars and other attractions. Along the trail, there are multiple places to camp or motels to use.  The last leg of the trail follows part of the Mississippi River north.

I think (?) 5 Hours will get you to the southwestern UP, no? I don't think there are many trails up there, but that's where I'd go.

David

Wisconsin: Green Bay & Door County?  I've never been to either, but they're on my list.

Pete Peterson at the Corner Tap in Reedsburg brews up a pretty good variety of beer. It's right at the start of the 400 Trail. 

Shawn C. said:

Depending on your location, this is about a 5hr drive: 400 Trail, Elroy-Sparta Trail, LaCrosse River Trail and Great River Trail. It's about 101 miles from the beginning of the 400 Trail to the end of the Great River Trail. Several small towns with restaurants, bars and other attractions. Along the trail, there are multiple places to camp or motels to use.  The last leg of the trail follows part of the Mississippi River north.

The Driftless Region of Wisconsin has already been mentioned, and I'll second that...

Also Southern Indiana - especially Brown County - is a fantastic cycling area.

Door County is crowded.  Madison has many great rides and breweries, beaches.  5 hours also puts you within the Stillwater Mn area, great on all counts and Hills!   

no way, even leaving from the north side of chicago it's a 6hr+ hour drive to cross out of Wisconsin.

From Chicago to Mt Bohemia, where I go snowboarding occasionally, it's almost 9hrs (with tag team drivers).

https://maps.google.com/maps?hl=en&q=holton+michigan&ie=UTF...

David P. said:

I think (?) 5 Hours will get you to the southwestern UP, no? I don't think there are many trails up there, but that's where I'd go.

David

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