Day 2 – 8/3 Vienna, OH to Menomonie, WI
The first morning of a long road trip always feels different.
Yesterday was about leaving home. Today, it finally felt like I was crossing America.
The morning began with a stop at Planet Fitness in Richmond, Indiana. One of the challenges of traveling by SUV is figuring out the daily routine, and a nationwide gym membership quickly proved its value. While I got in a workout and a hot shower, Jack patiently guarded the Tahoe from the parking lot. He’s becoming an expert traveling companion, although I suspect he’d vote to skip the workout and spend more time sniffing trees.
Back on the highway, the miles disappeared beneath the tires.
One of the highlights of the day came as I approached Chicago. Even from a distance, the skyline dominates the horizon. I’ve always enjoyed driving toward great cities, watching them slowly grow from tiny shapes on the horizon into towering skylines. For a few miles it feels as though you’re being drawn into the heart of the city.
Then, almost as quickly, the interstate bends west.
The skyscrapers fade into the rearview mirror, replaced by open highways stretching toward places I’ve never seen. There was something symbolic about that moment. Chicago marked the edge of the familiar. Beyond it lay Wisconsin, Minnesota, Canada, the Canadian Rockies, and eventually Oregon.
The unknown had officially begun.
Around 12:30 p.m., I stopped for lunch at City Works in Schaumburg, Illinois, just outside Chicago. It was another excellent brewery stop, a chance to relax for a while before continuing west. One thing I’m learning on this trip is that the destination isn’t the only adventure. Some of the best moments happen during these unplanned pauses—good food, a local beer, and watching the world pass by before getting back on the road.

By evening I crossed into Wisconsin, finishing the day after an impressive 672 miles. Rather than finding a campground or hotel, I pulled into Rest Area 62 near Menomonie. It wasn’t glamorous, but it was quiet, safe, and exactly what I needed after a long day behind the wheel.
As darkness settled over Wisconsin, I realized something.
The East Coast already felt a long way behind me.
Tomorrow, I’d wake up knowing the Great Plains—and eventually Canada—were waiting.
Jack’s Notes 🐾
Dear Journal,
Dad abandoned me this morning.
Well…not really.
He disappeared into a building called Planet Fitness while I bravely stood guard over the Tahoe. Nobody stole it, so you’re welcome.
Later we visited another place where humans gathered around shiny glasses filled with things I wasn’t allowed to taste. I continue to believe this is one of the greatest injustices in modern civilization.
The really exciting part came when giant buildings appeared on the horizon. Dad kept pointing at them and smiling. I looked too, but honestly they didn’t smell like much.
Eventually the buildings disappeared, the traffic faded away, and we headed toward wide-open country.
I have a feeling we’re getting close to the really good adventures.
— Jack