Stewart and Michelle Schilling compare notes after the Dairy Roubaix. PHOTO BY KIERSTIN KLOECKNER
Stewart and Michelle Schilling compare notes after the Dairy Roubaix. PHOTO BY KIERSTIN KLOECKNER
There’s a reason we Wisconsinites are called cheeseheads. Our state, after all, plays leapfrog with California for the most milk production. Whether it is the expansive dairy farms in eastern Wisconsin or the smaller dairy herds dotting the driftless area, we are full of all things dairy, including bike events.

Deep into the fabled area which cyclists either flock to or run from, lay the routes for two of the best bike events to which I’ve ever been exposed. If you have ever done either the Dairyland Dare or the Dairy Roubaix, both put on by Michelle and Stewart Schilling, you know there will be cows, hills, burning legs, sweat, tears and more hills. Oh yes, smiles are mandatory as well. 

Did I mention the hills? 

I have found most folks I talk to around the Midwest know about the Horribly Hilly Hundreds ride, held June 14 this year, but I was surprised to find most didn’t know about the Dairyland Dare. For the brave riders who sign up for the latter event, starting from the Lands’ End campus in Dodgeville, Wisconsin, on August 9, the choice of routes ranges from 100K to 300K through some of the most beautiful landscape in the country. 

I’m not kidding. After living a number of places in the U.S. and spending some time outside of the country, I can say I have ever experienced anything like the driftless region as a cyclist. No, there aren’t “mountains,” but climbing hills with grades of 16 to 20 percent again and again feels a heck of a lot harder than anything I’ve tackled out West. Here there are no switchbacks where you can catch your breath, after all.

When Stewart and Michelle started the Dairyland Dare, they didn’t know if anyone would actually sign up for the 300K route, let alone finish it. 

This year, on the ninth annual ride, they will host over 1,400 sets of strong legs and lungs. The payoff, thankfully, is well worth the gallons of sweat these riders will lose while climbing those countless hills. There are views which stop people dead in their tracks and send their jaws to the pavement. Each road seems to be named “hollow,” “ridge,” “valley,” “hill,” “creek” or “coulee.” When you look at the course maps, you’ll be hard pressed to find a straight road. Instead, the route looks more like a drunken sailor tacking up wind. 

I’m relieved knowing the Dairyland Dare is held in August when my legs have sufficient miles on them to tackle the beastly hills. Dairy Roubaix, on the other hand, is a gravel grinder held in April – Earth Day weekend each year – a time when my legs may have been kissed by sunshine only a few times.

This brilliant event is like most true gravel grinders. It’s free or “pay what you can” and is completely unsanctioned. Although some folks come out to race it, most come out for the camaraderie and to simply enjoy the countryside around Wyalusing State Park, resting like a giant near both the Wisconsin and Mississippi rivers. The routes offered are a 54 miler and a 107 miler. Both are challenging, but the 107-mile option puts riders on hills so steep no compact crank is low enough. Think 20 percent grades covered in sand or gravel. I call these wonders “black-out hills” because just about when I think I’ll either pass out or puke, the crest comes into my narrowing vision and I get to rest for a few brief seconds on the following descent.

When I asked Stewart and Michelle how and why they started the Dairy Roubaix, they said it came to them after participating in the mid-May Almanzo 100 gravel ride in southeast Minnesota. They, too, wanted to see what would happen if they put on a free gravel ride.

They make it happen by using leftover supplies from other events they put on and in-kind donations (thanks to Kickapoo Coffee for supplying the pre-ride fuel, for example). About two thirds of the participants make a free will donation, and this year, $2,500 was raised for Dream Bikes and local Iowa County scholarships. Volunteers from Wisconsin Bikes For Good Inc. based in Dodgeville help make the event possible on a shoestring budget.

Although I’ve only known Stewart and Michelle for a couple years, I have to thank them for several reasons. First, they put on the first gravel grinder I’ve experienced. Second, they spend hours upon hours putting together amazing events for bike obsessed people while working full-time jobs at Lands End.

Third, they are some of the state’s best cycling advocates. Over the past year, Iowa County has been trying to pass local ordinances restricting group rides and making it almost impossible for cycling events to be held in the county. With the backing of several business owners in the Dodgeville area, the Wisconsin Bike Fed and the president of Bombay Bicycle Club, Stewart and Michelle were able to get the county to back down and reconsider what damage laws like this would have on rural areas.  

When I asked them why such issues have come to the fore, Stewart listed the parties responsible: inconsiderate road users (both cyclists and motorists), irresponsible event organizers and a small but vocal minority of residents.
On the other hand, there are a plethora of business owners who benefit greatly from these events. Think grocery stores, gas stations, hotel and restaurant owners. The positive impact on businesses goes beyond the day of an event. People often come out to the area to pre-ride the courses and leave money in the communities along the way.

Another positive outcome is the money raised for nonprofit organizations in the area. Since the Dairyland Dare’s inception, over $100,000 has been raised for local charities, and $20,000 will likely be added to that total this year.
Stewart and Michelle feel their mission, as event organizers, is to do the best they can within their rights. I would say they are going far and above as just good citizens. Every community in the country would be lucky to have these two.

In 2004, Michelle saw Stewart’s e-mail address on a flyer for the first QuadruPedal Spring Century, which benefited the Iowa County Humane Society (the ride is cancelled this year). She contacted him offering to volunteer. That moment was not only the beginning of their team, but also an amazing relationship. Shortly after QuadruPedal, they started what they consider the event most “near and dear” to their hearts: the Dairyland Dare in 2006. They followed up with the Dairy Roubaix and the Triple Crown. The Wisconsin Triple Crown, a series of three challenging rides, included Arcadia’s Brute, Kickapoo Kicker (both discontinued) and the Dairyland Dare.

I have met many amazing cycling event organizers in my day, but very few are so detail oriented and considerate as the Schillings. I can’t promise that your legs and lungs won’t scold you for signing up for one of their events, but I can promise one heck of a party after you finish.

Kierstin Kloeckner used to race bikes and now commutes by bike in Madison, Wisconsin, where she is a personal trainer and yoga/pilates instructor. She blogs at