The Ride to Red Wing: Meandering Through the Midwest

The rails follow the river.
The rails follow the river.

The planning session for the ride had been laughable. We were three old farts, card-carrying AARP members, edging into retirement. Gary had suggested a three-day trip to Red Wing, Minnesota. Dick fiddled with a recently acquired GPS. I unrolled a map. “What’s to figure out?” I’d asked. “We head west from Lake Michigan. When we hit the Mississippi, we turn right.”

The riders follow the rails to Red Wing, Minnesota, home of Red Wing Shoes.
The riders follow the rails to Red Wing, Minnesota, home of Red Wing Shoes.

The point of the trip was to get back in the saddle. A year earlier, Gary had been riding his Harley Road King near Duluth when he encountered freakish weather. “I saw a wall of water headed straight for me. There were no overpasses to hide under. So I stopped and braced myself.” A derecho, the 100-mph microburst that can precede a Midwest storm, flung the bike like a child’s toy, throwing Gary to the ground with a crushed foot and broken hip. He watched his windscreen spiral into the sky, on its way to Oz. It was never found. Trapped under the bike, unable to move, he thought he would drown before help arrived. A year of therapy, not to mention work on the bike, and he was ready to ride.

I was coming off a situation only slightly less extreme. For a year, my wife and I had tried to sell our house. The process involves something called “decluttering.” Not unlike living in a padded cell while a stream of strangers walked through my life. My BMW had been imprisoned in the garage, behind a wall of cardboard boxes. It had taken me two days to dig out my riding gear and prep the bike.

Dick was slowly handing his photo studio over to his son. He’d bought a BMW F 700 GS and enough electronics to stock a Best Buy and was eager to try them out.

The night before we left, I’d watched “On The Road” and listened to Dean Moriarty explain the nature of spontaneous road trips: “We were leaving confusion and nonsense behind, performing the one noble function of our time…to move.”

We started early from our homes near Chicago. The ground fog formed a false horizon, above which floated a pale white oval. At first, I thought it was the setting moon, spreading the way the sun does, puddling like candle wax. On approach, the disc became a water tower perched like a golf ball on a tee, the name of a town emblazoned on its side. Nothing says prairie like a water tower. For the next two days, these water towers acted as old-school road maps, announcing the towns along the way.
Just miles from Chicago we encountered farmland. One-word signs, weathered with age announced: HAY. SOD. CORN (the latter sometimes adding the qualifier “SWEET” to distinguish their offering from corn grown as feed or ethanol). Out here, everything that is not road is a cash crop.

TripAdvisor says that there are 62 things to do in Galena, a tourist mecca. Numbers 1-61? Finding a parking spot.
TripAdvisor says that there are 62 things to do in Galena, a tourist mecca. Numbers 1-61? Finding a parking spot.

We rode through towns that haven’t seen a paint salesman in this century. Every other house posted notice of a garage sale. We passed a house, the front yard filled either with incredible antiques, or debris from a flood. There were signs of desperation, signs of pride. I noticed details: a mailbox shaped like a John Deer tractor, another with a planter of flowers. This was how people living on a rural delivery route announce themselves. Every town had a civic directory on its border—like knights of old hanging shields on the walls of Arthur’s court, to signify alliances. Here there be Lions and Rotarians. Baptists and Lutherans. The local legends who won the AAA high school state championship some decades in the past. It’s the same town, over and over—the water tower, the body shop, the salon where women pamper their nails, the bar named for whatever road you’re on.

As we neared the Mississippi the terrain changed. We wound through hills, threaded exposed rock bluffs. The signs now announced ski resorts, golf courses and equestrian academies.

Red Wing, Minnesota, is home to really big kinky boots.
Red Wing, Minnesota, is home to really big kinky boots.

In motion, you notice other things in motion. Sort of like entering a dance hall. The moment comes when you don’t see the floor, only the dancers. I became aware of two egrets, necks outstretched, wings pulling them forward just there. A chevron flight of geese. A hawk flaring its wings, landing atop a fence post. On the river, the white wake of a speedboat. A three-engine train pulling 100 boxcars, light glinting off the steel wheels.

A road trip reminds one that the business of America is motion. That rails follow rivers, that roads follow rails. We followed the roads. It was a sublime state, approaching grace.

Spending the night in Red Wing, we woke to a crisp, cool morning. We set out, the river on our left, and almost immediately felt the dance of movement. A tug pushed four barges, the white curling wake stark against the indigo water. A bicyclist pumped down the side of the road. Someone walked a dog. In a field, a bull mounted a cow. Each, in its way, winding the watch stem that turns the world.

The bluffs on the western side hold the highway close to the river.
The bluffs on the western side hold the highway close to the river.

We stopped for breakfast in Wabash, a small town of immaculate brick buildings, home to the Delta Queen paddlewheel riverboat. We parked near a statue of an important Native American chief, whose name was spelled differently on each block of the city. The attentive waitress topped off our coffee every three sips, and told us stories about the town, the kind of detail no plaque can capture.

We decided to go old school, to get information face to face. A group of bikers coming in for brunch told us the Iowa side of the river was worth exploring. They were not mistaken. The road caressed the flanks of 600-foot high hills—bluffs carved by the river’s relentless quest to return to sea level. You cannot follow the river without sensing that power. There were islands, wildlife, trees and scenic turnouts worth interrupting our momentum.

On the eastern side you find quaint towns like Prairie du Chein, home to Pete’s poached burgers since 1909.
On the eastern side you find quaint towns like Prairie du Chein, home to Pete’s poached burgers since 1909.

In Prairie du Chien, Wisconsin, we parked near Harleys tied to a hitching post on the shady side of Main Street. We asked one of the women where she liked to eat. She pointed to the line of people waiting at Pete’s Hamburgers, an outdoor stand that has been serving poached burgers with onions since 1909. Waving her hand down the street, she approved of the fried cheese curds at another restaurant. Finally, her companion pulled her away, saying, “Now dear, leave these gentlemen be. You know how you get when the meds stop working.”

The fried cheese curds were great.

The wild bunch stops for scenic markers.
The wild bunch stops for scenic markers.

We fired up and simply meandered. Meandering is the most spiritual form of motion. We rode through a town where families sat in lawn chairs in their front yards, facing the street, as though expecting a parade celebrating some previously unknown holiday. On a side street an unusually high number of people were sitting on John Deere lawnmowers. A precision drill team? The National Guard making do with whatever? A float peeked out from behind the outfield fence on the baseball diamond. The townspeople waved at us. We were the parade.

And then came the kind of moment you ride for.

Gary was leading, noticed horse droppings on the shoulder of the road, and slowed. Ahead I could just make out the rear view of an oddly shaped vehicle. We overtook a convoy of horse-drawn wagons, filled with Amish families on their way to church. The men wore hats, the women bonnets. A young girl sat on a rear-facing bench seat. She waved at us, bashfully. I waved back. We were partners in the great dance.

The highway climbs the bluffs on the western side of the Mississippi, giving a breathtaking view of Old Man River.
The highway climbs the bluffs on the western side of the Mississippi, giving a breathtaking view of Old Man River.
Map of the route taken by Bill Tipton/Compartmaps.com
Route map created by Bill Tipton/Compartmaps.com
Put a penny on the track. Roadside attractions in Bay City, Wisconsin, include a SOO line (now the MOO line) caboose converted to an ice cream stand.
Put a penny on the track. Roadside attractions
in Bay City, Wisconsin, include a SOO line (now the MOO line) caboose converted to an ice cream stand.
Along the road are numerous farmers’ markets like this one.
Along the road are numerous farmers’ markets like this one.
The GPS is purely decorative. Just ride.
The GPS is purely decorative. Just ride.
Main Streets in the Midwest have cornered the market on red, white and blue bunting, like these decorations in Galena, Illinois.
Main Streets in the Midwest have cornered the market on red, white and blue bunting, like these decorations in Galena, Illinois.

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