been looking around and i am totally into a weekend drive/ride trail/beer-bbq/hot tub house rental situation with a crew. does any one have suggestions on cities with decent amenities but close to good trails? i have not spent much time at all in the cheese state aside from Milwaukee.

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Southern Wisconsin is hilly and beautiful around the Lake Geneva area.  There are trails to get you to Lake Geneva from Chicago via the Prairie Path, Great Western Trail, and Fox River trail among others.  Those trails aren't phenomenal but the backroads of Southern Wisconsin are.  There's lots of rolling hills that you can ride all day on.

New Glarus, the Sugar River trail goes right through it. Beautiful country.

 

http://dnr.wi.gov/org/land/parks/specific/sugarriver/

I recently rode the Badger trail from Brodhead Wi, north to Madison. Mostly shaded, with a great tunnel. It's an old railway trail, so gradient change is low. I wouldn't rate the path as smooth, but my 35c tires worked  fine. From Madison, I took the Military Ridge Trail west to Mt. Horeb, to have lunch at the Grumpy Troll;-). Then I took roads south to New Glarus. That was an awesome hilly ride, and mostly downhill. Some steep climbs, but worthy downhills. Mostly farmland, but some minimal wooded areas. Then I returned to Brodhead. I did this trip over 3 days about 2 weeks ago. Great riding. Madison has some great trails, and big bike culture too. I got my bike maps from http://www.bfw.org/store/index.php. Have fun!
Don't miss the "400" and Elroy-Sparta trails in SW Wisconsin. About an hour NW of Madison, near the Dells. Not particularly challenging, but the scenery is absurdly beautiful. Reedsburg has all the amenities,including a local brewmaster.

Thanks for the link Dave,

 

I'm doing the Elroy-Sparta trail in July.

Dave Jacque said:

Don't miss the "400" and Elroy-Sparta trails in SW Wisconsin. About an hour NW of Madison, near the Dells. Not particularly challenging, but the scenery is absurdly beautiful. Reedsburg has all the amenities,including a local brewmaster.

I love the Kettle Moraine trail system.  I've only been there once, but I'd like to go again.  Lots of great singletrack with good technical challenges and some pretty good hills.  It's not too bad of a drive, when I went we made a day trip out of it.  Leave early, ride yourself dead, then drive back.

 

Map to Kettle Moraine

If you are looking for some good back road rides Backyard Bikes has some really good routes on their site and Whitewater and Lake Geneva is not far from that area. If you are looking for some mountain biking Kettle Moraine (same area) is the best place around that is not hours to get to be car. If you want a bit more of a city settleing Madison is really bike friendly and has some good riding. A lot depends on what type of riding you are looking to do, there is a lot of varity up there. Backyard Bike

I'm thinking about camping in Kettle Moraine State Forest Southern Unit next month and will be using the Hank Aaron State Trail, the Oak Leaf Trail, the New Berlin Recreational Trail, and the Glacial Drumlin Trail.  Of these, only the Glacial Drumlin Trail requires a trail pass.  This is $20 annually, or $5 per day.  to get an annual pass,  go to www.bfw.org and shop their store.
The first question I would ask is are you looking to ride roads or trails?  Wisconsin has some great spots for both.  If you are looking for a mix of both (and are planning to bring two bikes) there are some great hilly roads and flat old railbed stone trails in the Elroy-Sparta area.
i am down to ride either, road or trails. i just noticed there were lots of trails which i am down with but we all ride roads on the regular so i am into it. just want a weekend trip or two. ride, beer, sleep, repeat. ha!
excuse me *roads*

A further drive, but Trempeleau is supposed to be awesome for road riding....  My first ever camping experience was there with some friends in college....  Perrot State Park....  We camped there for a weekend at the LaCrosse Oktoberfest in 1991....  I wasn't into riding back then....  But the area has gotten great reviews and it was written up in Bicycling Magazine a few months back....  We also had breakfast at little bed and breakfast while we were up there....  I would love to up there and explore the area on a road bike one of these days....

 

http://dnr.wi.gov/org/land/parks/specific/perrot/

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