I spent the summer watching Lael Wilcox’s tracker as she rode around the world and ultimately broke the Guinness world record. As luck would have it, I had the opportunity to ride with her on the last day as she headed to Chicago. I couldn’t help but be inspired by her to plan an adventure of my own. I’d been toying with the idea of riding from my front door to Madison, Wisconsin, stitching together various trails to avoid busy roads.
The Planning
I worked with my cycling friends to fine-tune the route, asking for suggestions regarding unfamiliar sections. I wanted to take my favorite area trail, the Des Plains River Trail (DPRT), north until it ended near the Wisconsin border. But the section between the end of the DPRT and just north of Racine, WI, was more of a challenge. Not knowing if I’d take this adventure solo, I prioritized avoiding sketchy neighborhoods and high-traffic roads.
One route would require adding 10 miles to an already 85-mile route to reach low-traffic country roads. That option wasn’t ideal. After much research, I settled on a more direct route with a 25-mile segment on the frontage road adjacent to the I-94 expressway. It wouldn’t be the most scenic portion of the two-day ride, but it had a wide shoulder and hopefully minimal weekend traffic. In addition, there would be no shortage of pit stops for food and bathroom breaks.
I selected the October 19-20 weekend and kept tabs on the weather a few weeks out. The thought of battling a north wind had me worried. Not only would it be chilly, but I’d likely be contending with a headwind for 85 miles! But lo and behold, a week out, the forecast was a cyclist’s dream – sunny skies, 70s, and tailwinds the whole first day. Hallelujah!
Lael’s invitation to have people ride with her as she circumnavigated the globe inspired me. Pop-up rides and parties followed her like the Pied Piper on a bicycle. In that spirit, I contacted several local and Wisconsin friends and invited them to join me for any part of the ride.
Day 1 – Chicago Suburb to Brookfield, Wisconsin (85 miles, 2077 ft elevation gain)
I selected my gravel bike for its comfort because much of the ride would be on crushed limestone. Due to road construction, I adjusted the first few miles the night before our departure. As with any ride, you must always be flexible and ready to implement plans B, C, or D.
As my friend and I prepared to set off from my front door at 7 a.m., the sun had yet to rise, and it was a brisk 46 degrees. I powered up the SPOT GEN4 tracker I was testing (keep an eye out for a review soon) and shared a link with friends and family eager to follow our journey. With just the two of us riding, the tracker offered peace of mind with satellite tracking, messaging capabilities in case of spotty cell service, and an S.O.S. feature for emergencies. It also lets folks keep tabs on our progress. Additionally, my Garmin Edge 1040 Solar has LiveTrack enabled, which a couple of friends keep an eye on.
The first few miles had us riding neighborhood streets before jumping on the DPRT. Steam rose from the river since the water was much warmer than the air. As we pedaled north with a soft south breeze at our backs, the sun peaked through the trees, illuminating their gold and orange fall colors. We were alone on the trail, except when the peacefulness was interrupted by deer leaping across the path and a few squirrels foraging for food.
Another friend joined us about ten miles into the ride, planning to escort us to the end of the DPRT, about 20 miles north. We stopped for snacks and the bathroom before hopping on the road to head slightly west and then turn north along the I-94 frontage road. The road had a wide shoulder with very little traffic, probably because it was Saturday and businesses along the route were closed. The south wind provided a welcoming tailwind plus kept highway I-94 traffic noise minimal.
Pedaling north, we passed the Haribo gummy bear factory and Mars Cheese. Next time, I’ll have to check if Haribo has tours. Apple Holler, a popular orchard with parking spilling onto the shoulder, was farther up the road.
Around noon, it was time to think about stopping for lunch. We were close to Racine, WI, and our choices were fast food or fast food. Culvers has outdoor seating, allowing us to watch the bikes. As we ate, several people stopped to ask where we were heading, curious about our adventure. A few folks even said they wanted to ride with us if they had their bikes. It was exciting to inspire others.
It started to get hilly as we turned west at 6 ½ Mile Road (yes, that’s really the street name) and then north. Finally reaching the Milwaukee County Sports Complex, we jumped on the Oak Leaf Trail’s Root River Line. The trail is a combination of paved paths and parkways. It meanders along the Root River through neighborhoods, forests, wetlands, parks, and an arboretum. At one point, we came across something I’d never seen ― an albino squirrel. Unfortunately, I couldn’t get my phone out fast enough to take a picture. It’s incredible that the squirrel survived to maturity with no way to camouflage itself.
As we continued riding on the parkway, a sign read, “Beware of Flying Discs,” exactly then, a Frisbee flew by. Thank goodness for helmets. Farther along the trail, we encountered flooding, but the water receded enough that it was only 4-6” at its deepest.
Around 80 miles into our day, we took a sharp left off the Oak Leaf Trail and west onto the New Berlin Recreation Trail. This paved trail is straight as an arrow, heading east-west for only 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. We quickly noticed it was void of any real character ― no trestles, tunnels, or trees ― as it parallels a working railroad and passes beneath power lines.
We were only riding five miles of the trail to a hotel in Brookfield, WI. Our bags were waiting for us at the hotel, delivered there by a friend in town for an event.
Day 2 – Brookfield, WI to Cottage Grove, WI (62 miles, 958 ft elevation gain)
It was a beautiful sunny morning as we got back on our bikes and continued where we exited the trail the night before — heading west on the New Berlin Trail into a headwind that we’d “enjoy” the entire day. After two miles, we meandered through the quiet streets of Waukesha, WI, and picked up the Glacial Drumlin State Trail at the Fox River Sanctuary.
The trail gets its name from the glacial formations left behind. Drumlins are rounded, elongated hills shaped like half a cigar. They are made of the jumbled rocks, gravel, and soil left behind by moving glaciers. They are often covered with trees because their soil is too rocky and steep for plowing and farming.
Per TrailLinks, “the landscape challenged the Chicago and North Western Railway’s builders as they established the rail line between Madison and Milwaukee in the 1880s. The wooden pilings that supported bridges sank in the deep muck of extensive wetlands, creating dangerous passages for trains. Declining rail traffic forced the railroad to stop using the route in 1983, and it was transformed into a rail trail in 1986.”
The Glacial Drumlin is a typical rails to trails ― straight and primarily crushed limestone ― with an appearance similar to a long country driveway. Being a state trail, it requires a daily pass costing $5/day or $25/year. We would be riding the entire length of the 52-mile Glacial Drumlin Trail ― 13 miles of asphalt and 39 miles of crushed limestone. It travels through 10 small towns with minimal amenities on the trail. The online trail map shows 12 bathrooms; however, a couple were locked, and there were no port-a-potties at the trailhead parking lots. The website states that they are primarily open during the summer, but we found the Lake Mills depot had open bathrooms and showers.
There are several trailside ice cream, coffee, and bike shops. Mama D’s Café in Wales, WI, is a must stop. The trail is open year-round, with snowmobiling and cross-country skiing in the winter.
The trail offers plenty of wildlife, which is even more abundant during the summer. For most of the ride, we tried to avoid chipmunks that would stick their heads out of the holes they dug in the middle of the trail. It felt like a real-life whack-a-mole game you didn’t want to win. A bonus to the game was avoiding Isabella tiger moth caterpillars crawling across the path.
The highlight was when my friend spotted a bald eagle perched in a dead tree along the Rock River. We paused on an expansive wooden bridge, watching and hoping to see it grab a fish out of the river, but no such luck.
Our ride ended at the Cottage Grove trailhead which is just east of Madison, the capital of Wisconsin and home of the University of Madison. Our friend awaited us to arrive at the trailhead, and we all drove home after lunch at a local restaurant.
Final Thoughts
Would I do anything different? That’s a hard no. The time of year, mid-October, was perfect as we were mesmerized by the beautiful fall foliage. The temperature was ideal, 70s both days, with favorable winds on Saturday but headwinds on Sunday. Some stretches without tree cover, especially along I-94, would have been brutal on a hot summer day. The route was great, and I recommend riding the section along I-94 on a weekend when traffic is minimal. Or, if you don’t mind adding about 10-15 miles, there are quiet roads several miles west that parallel I-94 for part of the way north.
I encourage you to also be inspired by Lael and plan your own bike adventure. It doesn’t matter if it’s one day or three months ― get out there. It’s so rewarding.
Gear Selection
My gear selection was spot on. Below is a list, including links to my past reviews:
Trek Domane endurance bike
Trek Aeolus Elite 35V wheels and Girona RSL GR 700×38 gravel tires (tubeless with sealant)
Topeak Tubular handlebar bag to carry snacks and layers of clothing
Trek RSL MTB shoes with SPD 2-bolt cleats
Garmin Edge 1040 Solar LiveTrack activated, route navigation, and never needed charging
Garmin Varia RTL 515 rear radar with light
Bontrager ION front light
SPOT Gen4 tracker – Review to come at a later date
Bib choice for the two days included cargo pockets, awesome chamois, and nature break friendly design, so I would need to remove my hydration pack for bathroom stops.
Day 1 – Rab Cinder Cargo Bib Shorts
Day 2 – Jelenew Quick Release Zipper Bib Shorts
Resources
TrailLink – Glacial Drumlin State Trail
TrailLink – Des Plaines River Trail
As initially seen on Road Bike Rider
Sunflowers and Pedals 