Illinois is home to two of the most iconic road trips in the United States. Route 66 and the Great River Road. I drove both, alone, and the contrast between them said more about America than I expected.
When people think about Illinois, they usually only think about Chicago. The skyline, the deep dish, the lake. But Illinois is one of the few states in the country where you can drive two of the most iconic road trips in America without ever crossing a state line. The Great River Road, which follows the Mississippi from the Wisconsin border down to the south, and Route 66, which runs from Chicago across the plains toward the southwest.
I drove both of them, starting from Chicago, heading north to Galena and then south along the river to Alton, and looping back up through Route 66. What I found was not what I expected. It never is.
Why two road trips, and why alone
I planned this trip the way I plan most of my road trips. A rough route, a flexible calendar, and no one in the passenger seat. Traveling alone changes how you move through a place. You stop more often. You take the longer road on purpose. You skip the interstate because the interstate has nothing to show you.
That became the rule of the trip. Avoid highways whenever possible, stop whenever something looked interesting, and let the day end wherever the light was best for photos. A hundred miles, which sounds like half a day of driving on paper, became a full day of small detours and quiet towns. The distances on the map stopped meaning anything after the first few days.
Illinois turned out to be the perfect state for that kind of travel. It is big enough to feel like a journey, but not so big that you spend the trip exhausted. And it gives you two completely different versions of America in one loop.
The River Road: a side of the Midwest people rarely talk about
I started by driving north from Chicago to Galena, a small town tucked into the hills near the Iowa and Wisconsin borders. Galena is the kind of place that feels older than the country itself. Red brick buildings, narrow streets, a slow pace that has nothing to do with tourism and everything to do with the way the town simply decided to stay the way it is. I spent two days walking around, eating well, and trying to understand why a town this small had so much character.
From Galena I followed the river south. This is where the trip surprised me the most. The Great River Road is sold as a scenic drive along the Mississippi, but what struck me was not the river itself. It was how different the river looked from one section to the next. In some stretches it felt like a lake, wide and still, with small marinas and people fishing from wooden docks. In others it became a thin border, almost forgotten, separating Illinois from Iowa or Missouri without making a show of it.
Moline was my next real stop. From there I kept driving south through smaller towns I had never heard of before this trip. This is where I started noticing something I had not read about anywhere. The towns along the river feel traditional, but they look forward. Farm to table restaurants in places with three streets. Independent coffee shops in towns where you would expect a gas station and nothing else. Young people running businesses in buildings their grandparents probably worked in.
This is the part of the Midwest that gets ignored in the bigger conversation about American travel. People talk about the coasts and the national parks and the desert southwest, but the Midwest is the part of the country that actually feeds it. The farms stretch as far as you can see, and the towns built around them are reinventing themselves quietly, without asking for attention.
By the time I reached Grafton, just north of Alton, the trip had taken a new shape. Grafton sits where the Illinois River meets the Mississippi, and the Aerie’s Resort overlooking the bluffs gave me one of the best views of the whole drive. I spent a full day at Pere Marquette State Park, doing nothing more ambitious than walking, sitting, and letting the spring weather do its job. May is a generous month in Illinois. The trees were full again, the rivers were high, and the towns were waking up after a long winter.
Then I arrived in Alton, and the trip changed again.
Alton, and the unexpected feeling of home
Alton is not what I expected. I had read about it as a historic river town with a heavy past, and that is part of it. But Alton has the same energy as some of the districts in Berlin, where I live. Independent cafés, small bars, restaurants that take their food seriously, a creative scene that feels confident without being loud. It is young, it is cool, and it sits right next to towns that feel a century older.
There is also a strong ghost story culture in this part of Illinois. Several towns along the river are known for their haunted histories, and the locals talk about these stories openly. Not as a marketing trick, but as something woven into the identity of the place. The Mississippi has carried a lot of history, and not all of it is comfortable. The towns along it do not pretend otherwise, and I respected them for that.
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Route 66, and the road built for memory
From Alton I turned east and joined Route 66, heading back up toward Chicago through Pontiac. This was a completely different kind of road trip.
Route 66 is not really about today’s America. It is about a version of America that mostly exists in memory now. The diners, the neon signs, the murals, the gas pumps from another era. Some of it is genuine, some of it is built for nostalgia, and a lot of the souvenirs are mass produced and made on the other side of the world.
But if you look past the obvious, the road still hides real treasures. In one small town along the route I found a 1946 Illinois license plate, made of wood, from one of the few years the state used wood because of metal shortages after the war. Holding it in my hand, I understood what Route 66 is really for. It is not a road trip about the country today. It is a road trip about remembering what the country used to be.
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Two roads, one state, two Americas
By the time I got back to Chicago, the contrast between the two road trips was the part of the journey I kept thinking about. The Great River Road is the Midwest looking forward. Route 66 is America looking back. Illinois holds both of them, one ending where the other begins.
If you had to pick only one road trip in the United States this year, would you choose the road that tells you where the country has been, or the one that quietly shows you where it is going?
