A Story of Cycling, Friendship and Perseverance Along Wisconsin's Glacial Drumlin Trail 

The worst bike rides can sometimes become the best bike rides. Show me an easy, uneventful ride and I'll show you a boring ride that you'll forget as soon as it ends. Show me a ride with obstacles to overcome and I'll show you a ride you'll remember for the rest of your life.

I've learned this many times but never more than the day I rode the Glacial Drumlin Trail, a 52-mile gravel path between Milwaukee and Madison in the heart of Wisconsin.

Our group's problems—which started with a flat tire before we took the bikes off the car—had nothing to do with the trail itself. The fact that the Glacial Drumlin is flat and gravel, as opposed to hilly and a road ride, became part of the solution. The trail map shows 14 trailheads between the two terminuses, for a total of 16 entry points, and all but 1.5 miles follow an abandoned railroad corridor. The ride snakes through cities and rural areas and crosses subdivisions and farms. I saw parents with children, joggers and hikers, fitness buffs and aspiring fitness buffs. You're never far from a trailhead.

We split our group of 10 men into two, sending the five faster riders to one end and the slower riders to the other. We traded car keys when we crossed each other—a technique we use often that works great and did so this time in an unpredictable way. Josh—who had badly sprained his ankle in a hike two days earlier—was in my group, and his derailleur broke shortly after we passed the other group. "I'm done," he texted. Someone in the other group had the tools necessary to take off the derailleur and cut the chain to essentially turn his bike into a one-speed. If we hadn't just passed the other group, Josh never would have finished the ride, and at least some of the rest of us wouldn't have, either.

Because the trail has no hills, Josh was able to keep pace with the group even with only one gear. The "new" chain fell off repeatedly. It helped that when we had to stop for him to put the chain back on, we were on a gravel trail and not on the side of a highway.

The highlight, for all 10 of us, was the sunset. The trail runs east-west, and even the group heading east—away from the sunset—was awed by it. I rode west, toward a purple, pink and orange tableau as the sun dropped below a marsh. A creek reflected those colors back into the sky. Even though we were hours behind schedule, I lingered to watch. We would have missed it if everything had gone smoothly.

The beauty of the sunset made everything funnier, prettier, better, more. All my senses crackled. The moon watched us, a silver-yellow eye wondering why these five men were giggling. My headlight turned the woods lining the trail an ethereal gray. A raccoon scampered across the trail, its eyes floating white dots. A rabbit kept pace alongside me to the right, its white tail bouncing, before darting into the trees. Bugs (so many bugs) pinged off my eyes, my cheeks—blech—my teeth.

Finally we saw the end. Mike's black Ford pickup sat bathed in light in a parking lot. Tim skidded to a stop, exhausted, giddy, silly. Rob spread out on the ground like a giant starfish. Suddenly a glowing light grabbed my attention. One hundred yards ahead of me, 1855 Saloon Bar and Grill shined as if overflowing with Shekinah glory.

I walked across the parking lot and barged through the doors. Only then did I remember I was wearing skin-tight black padded shorts, a neon yellow biking shirt visible from space and a look devoid of mental acuity. Josh hobbled in after me, his hands black with grease from monkeying with his chain. We looked around … white tablecloths … customers in their first-date suits … servers in pressed shirts … I didn't literally hear a needle scratch across a record, but I might as well have.

Nearby, we found a bar with a live band playing too loud, collapsed into our seats and ate enough to feed a small country, and that was just me.

Before You Go

Fifty-two miles separate the beginning and ending trailheads at 810 West College Ave, Waukesha, Wisconsin, and 200 South Main Street, Cottage Grove, Wisconsin. My group ended at Cottage Grove, which allowed us to ride through a wooded section at night, which I loved, but some riders might not.

Riders 16 and older need a Wisconsin state trail pass to pedal the Glacial Drumlin Trail.