Minnesota Monthly’s Border Bike Guide: A Winona Rider’s Take on Bluff Country

Winona was highlighted in a recent Minnesota Monthly feature: “Fringe Benefits – Exploring Minnesota’s borders by bike, from frozen rivers to gravel horizons.”

The piece centers on Chase Wark, a professional gravel racer based in Winona, who rides the Minnesota–Wisconsin border almost daily. Winona sits in a quirky spot geographically — Wisconsin lies both north and east of town, so the border actually runs southeast from his house rather than straight east.

His go-to route is Highway 61, which follows the Mississippi River south from Red Wing to La Crescent. He calls it one of the most beautiful roads around, since Wisconsin’s bluffs are visible across the river the entire way. It’s also a practical choice for cycling — rumble strips and a shoulder keep bikes separated from traffic, and he suggests riding midday to avoid rush hour.

For a longer ride, Wark extends this into a loop: south on 61 to La Crescent, west on Highway 16 (the Historic Bluff Country Scenic Byway) into Houston and the Root River Valley, then back north to Winona on any of the connecting bluff roads. He also has a nearby bonus route for checking Iowa off the list: County Road 2 between New Albin, Iowa, and Eitzen, Minnesota, which crosses the state line so many times that it’s hard to keep track of which state you’re in. He notes it’s a quieter ride than Highway 61.

Overall, the Winona section positions the area as a strong home base for border-focused cycling — one well-maintained scenic highway, a quiet valley loop, and an easy add-on into a second state, all within a single day’s ride.

Other Minnesota Borders Worth Exploring

Winona’s border ride is just one piece of the bigger picture in Minnesota Monthly’s Bike Minnesota guide. A few other routes worth knowing about:

• South Dakota border: Home to the DAMn (Day Across Minnesota), a legendary one-day, roughly 240-mile gravel race from Gary to Red Wing that starts at midnight and finishes out near the Driftless region by sunrise-lit stretches of the ride.
• North Dakota border: The Agassiz Recreational Trail near Crookston offers 52 miles of natural-surface rail-trail through sugar beet country, while the paved trails around Pelican Rapids lead into Maplewood State Park.
• Duluth/Twin Ports (Wisconsin border, north): Riders cross the Bong Bridge bike path into Superior, and in winter, some bike directly on the frozen St. Louis River between the two states.
• Canadian border (Ontario): Superior National Forest’s gravel roads between Ely and Grand Portage are a bikepacking favorite, with standout routes near Grand Marais like the Fire Box Loop and Devil Track Loop.
• The DUM (Day Up Minnesota): Chase Wark’s own creation, linking the Iowa and Canadian borders in one 473-mile push, following Highway 61 for much of the route north to Grand Portage.

Whichever border you’re closest to, the same idea holds: pick an edge of the state, and let it show you something new.