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Text: Jasmin Welter | Video & photography: Brian Vernor

As the third-largest city in the United States, Chicago boasts an abundance of cultural highlights, architectural gems, and exquisite coffee and cuisine. All that comes paired with a seemingly endless Lakefront Trail and friendly people teeming with Midwestern charm.

As a year-round commuter, I’ve come to love my daily adventures on my way to work. Because I generally run late in the mornings before I’ve had my coffee, I usually skip the scenic route by Lake Michigan and ride the straightest line possible through the city to get to work. This takes me through lovely neighborhoods like the Southport corridor, past Chicago’s iconic Wrigley Field, through beautiful Lincoln Park and the bustling, ever-changing Loop.

After a long day at work, however, I wind down by returning home along the Lakefront Trail. There is not a more calming feeling than taking in the grandeur of Lake Michigan as the sun sets over the skyline, fellow cyclists you’ve come to know throughout the years waving as they pass by.

Image by Jason Lee

While the city is convenient for bike commuters, recreational cyclists face quite a few obstacles — the elements (think merciless 20+mph headwinds, or extended periods of sub-freezing temperatures), limited diversity in route options due to the city’s flat geography, and the usual traffic frenzy that comes in a major metropolitan area. But since reality tends to be what it is, I have learned to work with what is given to me — or to work around it. 

Luckily, not all of Illinois is urban and pancake flat. Towards the state’s northwestern frontier, a cyclist’s paradise exists. Enter Galena, where hills and gravel routes abound, and the ratio of cars to cows is heavily dominated by the latter. 

A mere three-hour drive from Chicago, picturesque country roads and rolling hills greeted me and my riding companion Frankie Andreu. A former pro, Frankie has ridden and raced the most iconic routes in the world. Yet because he was born and raised in Michigan, he still appreciates the nostalgic sense of home that riding in the Midwest evokes.

Now let me say this: I don’t usually ride with Tour de France legends or former Olympians. Naturally, I was very eager to pick Frankie’s brain and observe how he works, on and off the bike. Once in Galena, we explored the picturesque downtown area for a few miles. Immediately, Frankie and I wondered if we already got in more elevation than doing our regular riding around Chicagoland — or Metro Detroit, respectively.

To close out the day, we found ourselves at the Galena Brewing Company for a casual dinner, discussing our ride for the following day, getting excited at the thought of uninterrupted miles through gorgeous scenery. Our route was set up to incorporate the essential elements of the Midwest: a hundred miles of beautiful farm land, endless rollers, and forests abounding with different shades of green, with our grand finale being the banks of the Mississippi River.

For the fun of it, we decided to stay off the roads and hit gravel as often as possible. I fell asleep peacefully, with a smile of anticipation on my face.

Waking up to rain and gray skies, we decided on an extended breakfast at the local Victory Cafe. Though our hopes of a fair-weather ride were dashed, we tackled the route in good spirits. After all, unfavorable conditions go with gravel riding like post-ride beers and chili. With dark clouds looming above, we rolled out on our metric century. Soon enough, we were thankful for the sprinkles that kept us cool during the climbs — and they kept coming.

Left: Photographer Brian Vernor, Frankie and Jasmin. Upper right: Breakfast of champions. Lower right: For fast mixed-terrain riding, the Schwalbe G-One is hard to beat.

While I held my own up the hills, Frankie casually zoomed past me on the descents, flicking his fingers off his levers as he sped by, gleefully yelling “No brakes, Jasmin!”

We approached one of the tougher climbs on our route, appropriately named Devil’s Ladder. Starting out with a 1km climb at 10% gradient, it released us into a deceptive downhill before we hit another wall, and then another. Just as we headed into climb, the sky opened up and unleashed its full humid heat upon us — including all of the mosquitoes in Illinois, apparently. However, knowing our rest stop and the banks of the iconic Mississippi were just around the corner — more like 15km and a few hundred feet of climbing —  we kept moving onwards and upwards. 

The town of Hanover was a compact collection of a few streets, perched on the banks of the Apple River. Its faded ambience seemed to come straight out of a Steven Shore photograph – gas station Americana at its best, capped by a memorable side conversation with a few locals and their take on conspiracy theories in US politics.

Topped up on water and slightly confused, we made our way towards the Mississippi. Frankie’s excitement to see the world’s fourth-longest river was almost tangible. 

Leaving Hanover, the weather began to turn on us once more. A storm appeared rather quickly, and the hot sun rays piercing through the dark clouds created a dramatic backdrop as we worked through fierce crosswinds on the final stretches of gravel road.

Just as the rain started to hit us, we heard a rattling freight train approaching. The scene could not have been more perfect. Alongside the spectacular skies, and the sensation of relentless, heavy rain drops on our faces, all of a sudden, we picked up the pace and the race was on. As the rusty but colorful freight containers roared past, I couldn’t help but smile at this little intermezzo and how alive it made me feel.

And as if this wasn’t the best feeling one could have during a ride, we were taking our last turn to our final destination. Before us, the majestic Mississippi spread out in all its vastness and beauty. Immediately, the sight of this essential pillar of American mythology made us forget the miles and hills our legs worked hard to cover, and we soaked in the spirit of what was once the last frontier.

For more information on where to find the toughest climbs and picturesque routes, contact, or explore Galena Country online –