Madison, Indiana

Cracker Barrel opened at 7:00 a.m., and I figured I’d have the place to myself. By 7:15, the parking lot was packed. Apparently, this was the local breakfast hangout. I ordered blueberry pancakes—still hungry from yesterday’s long ride—and was greeted by an unusually friendly staff. They weren’t just polite; they knew the regulars by name, swapped stories, and checked in often. It felt more like a small-town diner than a national chain.

By 8:00, I was back on the road for the nearly three-hour drive to Madison, Indiana.

Jefferson Proving Ground

As I neared Madison, I passed a sign that only partially registered: “Army... Nature Preserve...” That odd pairing made more sense as I followed a massive barbed-wire fence that stretched for miles. Every few hundred feet, bold signs warned: “Do Not Enter – Explosive Ordnance.” Nature and leftover munitions—didn’t really add up for me.

Eventually, I reached the entrance of what was once the U.S. Army Jefferson Proving Ground, operational from 1941 to 1995. Today, it’s known as Big Oaks National Wildlife Refuge. Most of the land is still off-limits due to safety concerns, and the small portion open to the public is only accessible weekdays and every other Saturday. Today wasn’t one of those Saturdays.

At the end of a long access road, I parked near a row of abandoned building and made myself some lunch. It was eerily quiet. The building behind me had a “Tornato Shelter” sign—a first for me. All around were remnants of the old Army testing facility—overgrown buildings, rusted infrastructure, and a crumbling headquarters with a busted door, rotting siding, and a speaker and light still perched awkwardly on the roof. It looked like time had simply been left to do its thing.

Around the corner, I came across a residential loop of repurposed officer housing—modest homes relocated from different parts of the base. The were all occupied and I wondered how people had come to purchase these. As I slowly drove through, several people waved from their porches. Life goes on, even in forgotten places.

Prop Walkers Model Boat Club

On my way back to the main road, I noticed a crowd gathered near a pond. High-powered water jets shot into the air, and sleek model boats zipped across the surface at ridiculous speeds. I had stumbled upon the Prop Walkers Model Boat Club competition.

Naturally, I pulled out my camera and hoped for some interesting photos.

I spent the afternoon photographing the races, chatting with club members, and soaking in the energy of the event. These were model boats—they moved with high speed and precision, with elimination heats, multiple classes, and racers who brought multiple boats. It rained heavily, the sun would come out, off and on. They never stopped racing dispite how much it rained. I stayed around until 3:00 p.m for the final race. I never saw any trophies, they simply packed everything up, said their good byes, and drove away.

Madison was just ten minutes down the road. I made a quick stop at Walmart to confirm I could stay overnight (I could), then headed into town to explore.

Madison, Indiana

Madison, Indiana feels… different. And I mean that in the best possible way.

Tucked along the Ohio River, it has this artsy, laid-back vibe that feels more like a small town in Oregon or upstate New York than what most people expect from southern Indiana. You roll in expecting cornfields and strip malls, and instead you find beautifully restored 19th-century buildings, art galleries, funky cafés, indie boutiques, and a charm that never feels pretentious.

I parked my van on West street. No parking meters, no signs, no one bothered me. I wandered the streets taking in main street, the architecture, all the people, the fountain, and the neighborhoods. There were families with toddlers, travelers (Mexican, French, Indian, Middle Eastern, etc.), a couple of locals who seemed to be living rough, many people with tattoos and warm smiles, neighbors catching up like it was a Sunday morning. The vibe was effortlessly cool, grounded, and authentic.

That openness and vitality are part of what makes Madison so memorable—and it didn’t happen by accident.

The town was founded in 1809, I learned, by John Paul, a Revolutionary War veteran and frontiersman who saw potential in the riverfront site. I stopped at the park where he was buried. What grew from his vision became one of the most important towns in Indiana’s early history—a bustling port, railroad hub, and commercial center. Much of that early architecture still stands today, thanks to a remarkable effort that began in the 1970s.

Recognizing its historic importance, Madison was selected as one of the first three pilot cities by the National Trust for Historic Preservation. What followed was one of the most successful preservation projects in the country. More than 2,000 buildings are now listed on the National Register of Historic Places. I believe the entire downtown has been designated a National Historic Landmark District—one of only 12 in the U.S. to receive that level of recognition.

First Lady Laura Bush even named Madison Indiana’s first Preserve America Community, honoring the town’s dedication to maintaining its architectural and cultural heritage.

The result? A town that looks like it stepped out of history, but feels alive and evolving. There’s real investment here—not just in buildings, but in community. You can see it in the lovingly restored storefronts, the flower-lined sidewalks, the preserved riverfront, and the friendliness in every corner.

Madison is a place that challenges assumptions. It redefines what a small Midwestern town can be—and reminds you that preservation isn’t about freezing the past, but keeping it vibrant and relevant for the future.

It was getting late, and I was starting to feel the day catching up with me. I was about to head back to Walmart for the night when I had a thought—why not just stay here? There were no signs restricting street parking, no meters, and from everything I could find, Madison doesn’t have any ordinances prohibiting sleeping in a vehicle. The street was quiet, the houses well-kept, and the whole neighborhood had a calm, welcoming vibe. It felt safe and peacful. So, I stayed put. Sometimes the best places to park are the ones where everything just feels right.