Jim Winkle's Bike Routes from Madison, Wisconsin

Most of these popular routes start from the east Arboretum entrance. A few have a sustainability theme... organic/local food restaurants, solar/wind energy, a farm that grows food for people (these are surprisingly rare), a farm incubator, and certainly biking itself is an earth-friendly way to travel.

These use Ride With GPS; download the free client if you have a smart phone. Upgrade to their Basic level and it will speak the route to you (and more).

I organize small group rides using these routes; contact me early in the season if you're interested in biking together. We average 10-12 mph and often stop for lunch or coffee. The rides get progressively longer throughout the season and occasionally culminate in a century ride for me.

I've gotten a lot of positive feedback about these routes, and even thank-you gifts (which was totally unexpected, but I'm grateful)! Let me know what you think of these rides.

"More dramatic elsewhere, perhaps more strange, more thrilling, more grand, too, but nothing that picks you up in its arms and so gently, almost lovingly, cradles you as do these southwestern Wisconsin hills." -- Frank Lloyd Wright

A rare round barn, outside of Viroqua, WI

Day Trips

Many of these are lovely rides, especially the longer ones. There are generally restrooms and water at the halfway point. Some of these rides require a state trail pass to make it easier to get out of Madison. 

I lucked onto this road at just the right day of the year (Oct 20).




Great Blue Heron

Century Bike Rides

One hundred miles in one day... it's really not that hard; you just have to work up to it. A good bike helps, too... the longest I had ever ridden was 30 miles, but immediately went 70 on my new bike, and the next weekend did my first century ride. Here are a few century rides, give or take.

If you do the full century, you might need to stop here and say a prayer :)

Weekend Bike Tours

Weekend rides (2-4 days).


1-2 Week Bike Tours

The new Google maps broke many of these routes, but the cue sheets are still good. I now use ridewithgps.com, which allows infinite customizations to a route (Google allows ten). I'll be redoing the older routes as time permits.

These are mostly in the Driftless region of Wisconsin, which has quiet roads (a few cars per hour) and decent scenery.  Do you know of other places in the US like this? Please contact me with your favorite places to tour!






I love how this road looks almost like a bike path

LaCrosse to/from Madison, Wisconsin

There are many ways to get between LaCrosse and Madison, Wisconsin. Historically, most people on tour took the packed gravel trails since they're impressed they can make it the whole way without going on roads. That's cool, but I find the flat terrain becomes boring and the constant grind on gravel gets old. Plus Wisconsin has *great* back roads, so the off-road trails are not needed by anyone with experience biking.

If you haven't biked in SW Wisconsin before, you're in for a treat! Most back roads are paved and lightly travelled (especially the non-numbered roads). They're hilly, because this is the unglaciated "Driftless" area of Wisconsin (en.wikipedia.org/wiki/Driftless_Area), which adds to their beauty. I love zipping down a hill and am willing to pay the price of going up a hill.

I have two routes: one from LaCrosse to Madison, and the other from Madison to LaCrosse. They are slightly different to take advantage of conditions that are better in one direction.

While I've probably biked on all of these roads, I haven't done it in one fell swoop nor recently. But the routes should be fine... there are very few bad roads in SW Wisconsin. Note that there is camping in Viroqua and LaCrosse, but the icons may be hidden by the grocery store icons.

Please let me know if you take one of these routes!

Other Rides

You'll generally need to drive to the start of these rides.

Thanks for reading; please let me know if it was helpful!