Driftless, Not Painless


Survey. Mill Creek. Dyerson. Just three roads that strike terror in the hearts of cyclists familiar with Southwestern Wisconsin’s “driftless” terrain.  The glaciers missed this area, and with elevations reaching 1,161 feet, these brutes are often featured destinations of the numerous cycling events that take place here from spring to fall. One such event, The Dairyland Dare, starts and finishes at the Comer Center, Lands’ End’s employee fitness facility.

I’ve always enjoyed cycling, but it wasn’t until I worked at Lands’ End that I discovered a true passion for it. I had heard about a group of cyclists who went on lunchtime rides from our corporate headquarters and one day I joined them. I wasn’t intimidated by the fact that 95% were men. Or 50% were half my age. Or that they wore neon cycling shirts and what looked like black girdles.  Or because their bicycles probably cost more than my Ford Focus. I was going to suck it up and ride.

That first ride was memorable. Memorable for its complete failure. Riding my cross-trainer, I trailed behind the pack from the get-go. Up the first hill? A piece of cake. The second hill? The sweat started to pour. By the third hill I was cursing all those young men in neon who left me in their dust. All except Terry, the leader of the group, who warned me: it gets tougher up ahead. LORD OH MIGHTY, WHAT? “Get a lighter bike,” Terry suggested. And that’s exactly what I did.

I purchased an introduction road bike and soon became a group regular. Those cyclists proved to be some of the most generous teachers I’d ever had, gladly sharing their accumulated knowledge: How to downshift while ascending a hill so your chain doesn’t fall off. How to position yourself comfortably in your seat when going downhill so you don’t feel like you’re going to flip over. And to always watch for animals, gravel and cars that can come up unexpectedly, potentially cause you to crash. Occasionally another rider would even offer a helping hand, gently placed on my back, pushing me as I struggled to climb a hill.

That first spring I trained for the 100K (67-mile) route event. To train I did hill repeats. Again. And again. I learned to wear cycling shorts in public without embarrassment. I learned to eat things like “Gu” and drink electrolytes without stopping. And after spending four months and 20+ hours a week in the saddle I thought I was ready. I thought. The morning of the event, surrounded by all that spandex, I was pretty nervous but I rode. And rode. And rode. And in just 7.32 (!) hours, I crossed the balloon-arched finish line to be greeted by a cycling friend, Dave, who ran to grab my bike as I was about to collapse and led me to a shady spot to sit and rehydrate. I guess I looked as bad as I felt. But I finished, and I didn’t walk up one single hill.

Despite that exhausting first event I kept cycling. Once I conquered the hardest hills in the area, everything else was just, well, downhill.

Why? Because my routes take me through forested hillsides that reach down to valleys cut into limestone bedrock beside trout streams with wildflowers and the frequent wildlife sighting. And I’ve learned a lot about how to motivate myself. I’ve learned that success is 95% psychological. But most of all, I keep going because of the freedom, the sheer fun of swooping up and down the hills of the beautifully sculpted “driftless” area. There’s nothing like it.

This year, the Dairyland Dare event that starts and ends at the Comer Center on the Lands’ End Campus takes place on Saturday, August 10. Care to join me?


Photos courtesy of: Al Lada.


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