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– We left the pavement early on the morning of Day 2, crossed the Root River and came face to face with a mile-long climb on a slurry of mud and gravel.

It was late May. Our group of five was a few miles south of Houston, Minn., and immersed in the Driftless Area, an ancient landscape of deep coulees and high ridges connected by long, snaking roads. Formed by 500 million years of wind, rain and snow melt, the region would define every aspect of our 230-mile ride from Winona to Lansing, Iowa, across the Mississippi River, and back through Wisconsin. We would feel every foot of elevation gain as we each hauled 30-plus pounds of bikepacking gear from valley floor to ridge top on a mix of gravel and paved roads. And we would experience more than the usual fare of that landscape-defining wind and rain.

But our immediate concern was the climb. Before long, all of us, including Tom McDowell, the strongest, and Pablo Armas, the youngest, had dismounted to push our bikes toward the summit. For Nina Clark, who used her 28-mile round-trip commute as the base for her training, it was an opportunity to see more of the wildflowers lining the road. The rest of us raised our heads reluctantly and admitted they were pretty.

The summit offered a new challenge: a sudden, driving rain powered by wind gusts reaching 50 miles per hour. Kristen Paulsen, who toured extensively in the Appalachian Mountains with her husband before taking time off to raise a family, felt herself being blown toward the ditch. Tom showed early signs of hypothermia. We needed shelter and found it in a farm’s machine shed. At the far end, a section of sheet metal roofing lifted in the wind, then slammed hard on the rafters in a rhythmic clanging that didn’t stop until the wind died and the rain backed off to a drizzle. We rode on, leaving tire tracks in the gravel driveway to baffle our absent hosts.

Day 1 had been so different: Delicious $5 burgers at the Witoka Tavern, a photo shoot with kids at the Houston Nature Center, a private tour of the International Owl Center, and, to the southwest, a night at Outback Ranch, a campground for horse people.

We reset on Day 2 in Spring Grove with an extended lunch and a detour to the local car wash where we lined up our rides, plugged in quarters and sprayed grit from five crud-encased bikes. The weather reset as well. By the end of the day, with nearly 40 miles behind us, we were rolling down a shaded gravel road, past a couple of trout fishermen enjoying a beer on the tailgate of their pickup, and into Dorchester, Iowa. Tom secured a campsite across Main Street from Wings Supper Club.

Dinner and Iowa-made Templeton Rye carried us through several hours of tornado warnings, broadcast nonstop on local television. We stepped outside to study the boiling sky, then returned to cocktails until the weather passed. We slept under stars and woke to the promise of sunshine and 70 degrees.

We reached Lansing, in the northeast corner, around noon on Day 3 with nearly 100 touring miles under our belts. Spread across a narrow strip of public land beneath the bridge that would take us across the Mississippi River and drop us in southwestern Wisconsin, we feasted on Kristen’s special blend of beans, rice and veggies, supplemented by snap peas sauteed in olive oil with fresh garlic.

We needed all of that meal’s nutrition for the afternoon ride. Rush Creek Road set the tone. Nearly deserted, the road allowed us to ride in clusters rather than the single file pattern of paved, busy roads, but it rose in an endless, energy-draining climb punctuated by steep rises that pulled us off our bikes. We walked until the grade moderated, hopped on our bikes to grind out another mile, then dismounted at the next rise.

Feeling relief

Water became an issue, solved at a farmer’s spigot near a yard sign proudly displaying a rifle and the words “We don’t call 911.” The farmer was helpful, but not friendly, perhaps the only person on the trip who took no interest in our travels. The ride resumed, mostly up, occasionally down, always through breathtaking scenery of trout streams, small pastures and wooded hillsides, until we reached camp feeling relief, triumph and exhaustion.

We still had tents to pitch, a meal to cook and two days of sweat to shower off. When the chores were done, Pablo heated water in our largest cooking pot, added a brick of Guatemalan cocoa and powdered milk, and treated us to pure hot chocolate.

By this point Nina knew there would be more gravel road tours in her future, Pablo discussed the merits of a touring specific bike, and Kristen, an experienced paved road tourist, marveled at the camaraderie that low-traffic gravel roads encouraged. Bike touring is part of Tom’s DNA, but this route pulled him in like a magnet. “It couldn’t be better,” he said, then said it again.

No one missed the gravel on Day 4, an all-pavement day with a net drop in elevation. Instead, we reveled in switchbacks that, at one point, had our group (“The Drifters”) staggered on three levels of road. I watched from the top as they swept through turns, disappeared behind a red barn, reappeared briefly in the shade of an oak, and chased a ribbon of concrete into a grove of trees.

Then it was my turn.

While Day 2 threatened us with hypothermia, Day 4 brought near heat exhaustion. We stumbled through camp set-up and retreated to cold showers. Dinner was tenderloin tips at Features Restaurant on the edge of West Salem, Wis., followed by a street dance downtown. The kids and families had gone home by the time we arrived, leaving only the drunks. It wasn’t our style. We turned in early.

Day 5 — Memorial Day — came with the promise of all-day rain and low temperatures. We were on the road by 7 a.m. By 8 we were drinking gas station coffee and eating bakery food, huddling under the eave at Kwik Trip. The all-day rain had arrived. It bounced on the concrete.

The route was mercifully flat along the Great River Trail, a narrow ribbon of land boxed in by the swollen backwaters of the Mississippi River and drenched from above. Seasoned veterans now, we ignored the weather and spent the morning talking, pedaling and peering into the bayou-like mystery of the flooded forest.

The mood changed near the town of Trempealeau, where a bathroom stop and extended break under another eave dropped our body temperatures. Hypothermia became a risk again. Conversational chatter disappeared, replaced by a focused effort to finish the ride. We rolled into the Amtrak station in Winona by noon, changed into dry gear and summoned spouses.

We were cold, wet and done with this trip, but also animated, posing for group photos and overflowing with stories. Bike touring has always had rewards and challenges, but this trip through the Driftless Area, with its stunning vistas, challenging hills and unpredictable weather, gave us both in spades. It won’t be the last.

Doug Shidell is an avid bicycle tourist. He publishes the Twin Cities Bike Map.

More details: View and get maps of the Driftless Area bikepacking trip at avenzamaps.com/a/zbpagod.

More details: View and get maps of the Driftless Area bikepacking trip at avenzamaps.com/a/zbpagod.