Red Barn Delight—Madison Area Cycling

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Are you looking for a fantastic challenge without leaving the Midwest? Roller coaster hills and and pastoral views? This ride is for you!

Written by

Kierstin Kloeckner


47.5 miles

This route will bring you into the edge of the driftless area—a part of Wisconsin untouched by glaciers. Because of this, there are hills galore. Be prepared to be a distance from towns, water sources and cell towers.

Destination Distance From Downtown

5.8 miles


4 of 5 diamonds

If you thought Wisconsin was flat, think again. This ride will test your strength and endurance but will give you beautiful views from every climb. A triple chainring or a compact crank is recommended since the hills will go up to 18%.

Time To Complete

3 hours

For the seasoned cyclist, this route will take about 3.5 hours. For those who want to enjoy the scenery and take things at a slower pace, 4.5 hours is suggested.


Spring, Summer, and Fall



Wisconsin is an agriculture state. It is known for dairy, corn and soy production, and yet the state has lost about 9,000 farms in the past five years.

To the East of Madison lay flat corn and soy farms.To the West and Southwest, however, endless hills with smaller farms are tucked into every valley. Welcome to the driftless area—a space untouched by the last glaciers that receded from the area 11,000 years ago. This is where you will find some of the most beautiful farms in the United States—almost all accessible by smooth roads first paved for the dairy trucks.

What Makes It Great

Thirty years ago, seeing red barns was common. Because these red barns are so difficult to maintain, many of them have fallen, one by one. This beautiful ride through the driftless area showcases close to fifty red barns—that’s almost one per mile! You’ll be treated to both wide valleys flanked by the hills, and narrow ones where farms seem to snake there way through. This area is also known for the plethora of CSAs (community supported agriculture) and organic farms.

As you head West out of Middleton, you’ll go through the towns of Cross Plains and Black Earth—your last two spots to grab some water or take a bathroom break until your return. Here is where you’ll also be crossing over the Ice Age Trail (a trail that runs the length of the state, following where the glaciers moved through). Take a moment to admire the old limestone houses, the rocky outcroppings, the wildflowers in the prairies and the enormous old oak trees.

As you turn West into the steeper hills, you’ll be treated to scenery which rivals Vermont and the Pyrenees as well as an old church that holds a “blessing of the bicycles” each summer. After all that climbing, come back into town for a well deserved meal and a local beer.

Who is Going to Love It

Because Madison is only a few short miles from the start of the driftless zone, you’ll be climbing hills in no time. This ride was meant for those who love a vertical challenge, but even if you don’t, the views from the top of each hill will take your breath away more than the exertion. Although there aren’t many towns to stop in for provisions or bathroom breaks, when you do come through one, you might find farm stands brimming with potatoes, honey, sweet corn or pumpkins. Just be sure to bring either a compact crank or triple chainring since a few of the rolling monsters top out at a grade of 18%. Also make sure you bring at least two water bottles.

Directions, Parking, & Regulations

You can start this ride anywhere along the route, however, the mapmyride route has you starting in downtown Middleton, a suburb just west of Madison. Here you’ll find taverns and breweries to grab a beer as well as some food after the ride, and cafes to get coffee or breakfast prior to the ride.

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Middleton, Wisconsin

1902 Parmenter Street
Middleton, WI, 53562
43.096133, -89.511937

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