The Road West: Indiana, Chicago & Our First Wisconsin Adventure

There is something about a road trip that makes me feel like an adventure begins long before you reach your destination.

For me, traveling isn’t just about getting from Point A to Point B. I love seeing what is along the way. I want to pull off the highway, read the historical markers, see the little towns, stand beside the water, find the lighthouse, and experience places that I might have completely missed if we had simply driven straight through.

And that is exactly how this trip began.

We packed up, hit the road, and started making our way west through Indiana, Illinois, and Wisconsin.

We had a much bigger destination ahead of us, but before we got there, Wisconsin gave us plenty to explore.

Through Indiana and Into Chicago

The first part of our drive took us through Indiana before heading into Illinois and the Chicago area.

Driving through Chicago is an experience all its own.

There’s the traffic, of course, because apparently Chicago believes a road trip isn’t exciting enough without adding a few extra lanes, a whole lot of cars, and a little stress.

But there is also something exciting about traveling through such a huge city and then watching the scenery begin to change again as you continue north.

Before long, Illinois was behind us and we crossed into Wisconsin.

That was when this part of the trip really started to feel like an adventure instead of simply a travel day.

Exploring Wisconsin Along the Way

One of the things I love about traveling is discovering the history of a place.

Wisconsin gave us plenty of that.

We stopped at historical markers, explored wooded areas, learned about the history of the Black River Valley and Wisconsin’s logging days, and came across stories I never would have known if we hadn’t stopped to read the signs.

One of those stories was about the passenger pigeon.

It is hard to imagine today, but enormous flocks of passenger pigeons once traveled across North America. According to the historical marker we found, one of the largest nesting areas ever recorded occurred in Wisconsin in 1871.

Those are the little things I love about road trips.

You can read about history in a book, but there is something different about standing in the actual place where that history happened.

We also stopped at an overlook surrounded by miles and miles of trees. Looking out over that landscape was one of those moments when you realize how much of the country you never see when you stay on the interstate.

And then there were the rock formations rising above the trees.

Wisconsin surprised me.

I think sometimes we picture a state one particular way before we visit it. Then you actually get there and realize how much variety there is: forests, rock formations, history, small towns, beaches, and the beautiful Lake Michigan shoreline.

A Stop in Kenosha

Eventually our exploring brought us to Kenosha, Wisconsin, right along Lake Michigan.

And this was one of my favorite stops.

We visited the historic Southport Lighthouse, which was built in 1866 on Simmons Island. It once served as an important navigational light for ships approaching Wisconsin from the Chicago area.

Standing there and seeing 1866 carved above the lighthouse door really put its age into perspective.

This lighthouse has been standing beside Lake Michigan for more than 150 years.

Ships have passed it.

Storms have rolled across the lake around it.

Generations of people have stood where we were standing and looked out over the same water.

That is the kind of history I love experiencing when we travel.

The North Pier Lighthouse

We also stopped to see the Kenosha North Pier Lighthouse.

The North Pier Lighthouse dates to 1906 and became the active harbor lighthouse after the Southport Lighthouse’s original navigational service ended.

The two lighthouses are completely different, which makes seeing both worthwhile.

Southport feels historic and traditional with its tall brick tower.

The North Pier Lighthouse sits out near the water and feels connected to Kenosha’s working harbor and Lake Michigan.

Seeing both helped tell the story of how important the lake has been to this area for generations.

And Then, Of Course, There Was Lake Michigan

I couldn’t visit Kenosha without going down to Lake Michigan.

I have a little travel goal that I absolutely love:

I want to stick my feet into every Great Lake, and I want to do it from different places whenever I get the opportunity.

It might sound simple, but those are the travel memories I treasure.

I don’t need every stop to be an expensive attraction or a perfectly planned excursion.

Sometimes I just want to take my shoes off, walk down to the shoreline, put my feet in the water, and think:

I’ve been here.

Lake Michigan is so large that standing on its shore can almost feel like standing beside an ocean.

And every section of shoreline feels a little different.

That’s why I don’t consider putting my feet in Lake Michigan once and checking it off a list. If I’m somewhere new along the lake and I have the opportunity, I’m probably going to find my way down to the water again.

It’s becoming part of the adventure.

Our Wisconsin Hotel Stay

After a full day of driving and exploring, we stayed at the Holiday Inn Express & Suites Racine by IHG in the Racine/Mount Pleasant area.

For a road trip, I appreciate a hotel that gives us a comfortable place to reset before getting back on the road.

Our room gave us space to settle in after traveling, and the hotel also had an indoor pool and fitness center.

Those amenities might not be the main reason we’re traveling, but they definitely matter after spending hours in a vehicle.

A good night’s sleep, a shower, breakfast, and the chance to recharge can make the next travel day so much better.

Where we stayed:
Holiday Inn Express & Suites Racine – our booking link

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Why I Love Traveling This Way

This part of our trip reminded me why I enjoy road trips so much.

Yes, we had somewhere we needed to be.

But we didn’t make the journey only about the destination.

We stopped.

We explored.

We read historical markers.

We walked through the woods.

We looked out over miles of Wisconsin landscape.

We found pieces of history.

We visited lighthouses.

And, naturally, I found Lake Michigan and got close to the water.

Those little stops turned what could have been nothing more than a long drive into memories.

That’s the kind of traveler I’m becoming.

I want to see the big attractions, but I also want to discover the places people drive right past.

I want luxury hotels and beautiful destinations someday, absolutely — but I never want to lose my love for pulling off the road because I spotted something interesting.

Because sometimes the unexpected stop becomes one of the best parts of the entire trip.