Day 27: Madison, IN to Jeffersonville, IN

Distance: 50.3 mi, Climbed: 2,569 ft
Completed: 1,030.1 mi, 53,003 ft

It’s definitely about the journey. Today’s 51-mile ride connected two well-known Ohio River towns—each with bridges crossing into Kentucky. While our route loosely followed the river, we spent most of the day a few miles inland on quiet rural backroads.

Before setting out, Rich and I went to the Madison-Milton Bridge to take in the view. From there, we rolled through downtown Madison, which had a relaxed Sunday-morning energy—people out and about, but in no rush.

A few miles later, we turned north and returned to farmland—long, uninterrupted stretches of fields that seemed to go on forever. Like earlier rides, we were rarely far from homes, whether set back at the end of long driveways, other times gathered in small clusters that marked the edges of tiny communities.

With no trees for cover, the wind became a steady presence—nothing dramatic, just enough to wear on the legs mile after mile.

There were only a few towns along today’s route. We stopped at a gas station for a quick break—Sunday made for limited options, with most places closed. Later, in Charlestown, we were hoping for a lunch spot, but the pizza place was not open. So we went to the only store open in town, the ice-cream parlor. Muffins and ice cream do make for a welcome meal.

As we enjoyed our lunch on the bench outside the shop, Amanda came over to wash the next storefront’s windows. We struck up a conversation about the ride. She proudly mentioned—rightfully so—that while bike riding wasn’t her strength, she excelled on the StairMaster. Amanda owns and operates a commercial cleaning company, and her son Ethan was working with her that day.

When we shared our epilepsy mission, Amanda mentioned she had been taught—like I was—to put something in a person’s mouth during a seizure so they wouldn’t swallow their tongue. I told her that I’ve since learned that’s actually dangerous, and that it’s impossible to swallow your tongue. We also talked about how seizures can look—sometimes a person’s lips may turn blue, which can be alarming, but it’s part of how the body responds as blood shifts away from the extremities to support the brain during a seizure.

Amanda and Ethan kindly shared a few recommendations for Jeffersonville and Louisville, and it was clear how much they enjoyed living in this part of the country. With fifteen miles still ahead, we said goodbye, grateful for the connection. 

About ten miles outside Jeffersonville, farmland began giving way to large-scale development—massive warehouses already built, with more going up. At one point, a connecting road was under construction, leaving us with a choice: detour a few miles or try to ride through. We took the chance.

The pavement quickly deteriorated—cracked, uneven, and broken in stretches—with exposed drainage pipes running along the roadside. It wasn’t exactly welcoming, and we made our way through carefully, staying alert and steady. We got through just fine—though the “DO NOT ENTER” sign suggested we might have made a questionable life choice.

Somewhere along that stretch, we crossed the 1,000-mile mark of this journey. No sign, no fanfare—just the quiet satisfaction of knowing how far we’ve come, one mile at a time.

That evening, we followed Amanda and Ethan’s recommendation and headed to Parlour, right at the base of the Big Four Bridge. It was open late, and the pizza hit the spot.

With Jeffersonville just across the river from Louisville, we’re looking forward to exploring the city tomorrow on a well-earned rest day.

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