2023 Spring Road Trip Day 2 Travel Log: Wandering Southeast Indiana, hoops and horsehide


My 5-day trip in April took me to Indianapolis, Cincinnati, Owensboro, a part of Old Route 66, and many other places along the way. I enjoyed it a lot! I made 27 unique stops in the 5 days, and putting it all under one report just isn’t going to do. So I have my travel log broken up into each day, to give you in idea of what it was like behind the driver’s seat.

Link to Facebook Photo Gallery (Days 1 and 2)


Day 2: Backroads, hills and the REAL Hoosiers

The second day of the five-day road trip began at a Super 8 in southeast Indianapolis. Before I checked out, the lobby staff let a guy lay on the floor to nap. Moving on …

I planned to make it to Cincinnati today and see where I was on time when I got there to figure out what I wanted to do the rest of the night and for Day 3.

The first stop for Day 2 actually is more of a true guess of a site. The Indianapolis suburb of Southport was where baseball Hall of Fame player Chuck Klein was born. He attended Southport High School and graduated in 1923. Klein was one of baseball’s greatest hitters during the 1930s, but few of today’s casual fans know of him because his stats were overshadowed by greater legends such as Babe Ruth, Lou Gehrig, Joe DiMaggio, Lefty Grove and Dizzy Dean. Klein, nicknamed the “Hoosier Hammer,” hit .320 for his career with 300 home runs and 1,200 runs batted in, and won the 1933 Triple Crown – one of the most glorious feats of baseball statisticdom.

The old Southport High School was a few blocks west of downtown, but was razed many years ago. Southport Park was another few blocks east of downtown, and I can only assume it was there where Klein and Southport High played their baseball games. That’s where I stopped at, at around 8 a.m. with the sun still beaming bright. Obviously much has changed in 100 years, but there is a baseball diamond at the park. Home plate location notwithstanding, I can mark this one down on the “famous sports athletes’ high school alma maters” road trip list of mine. I will write up a full list at some point.

The way from Indianapolis to my featured stop in Milan meant traveling on the historic Michigan Road, which cuts diagonally through the state, northwest to southeast, starting up north in Michigan City, Indiana. This road, which once was US 421, paralleled Interstate 74 at certain stretches. I decided to see what was out there between Indianapolis and Milan, although my friend Rex told me about a certain place in Greensburg.

The first primary pass-through was Shelbyville, a town of about 20,000 people. The most amazing thing that I saw there was displays of art work found on the city’s traffic light control boxes. Typically, these boxes are just a bland, boring lug of a thing that sticks out from the ground. More often than not, they are made of shiny silver steel. However, in Shelbyville, these boxes are given visual appeal with wrap-around art. What a way to bring color to town!

Shelbyville also has an old high school building close to downtown. I mention this because it’s quite unusual for a high school building to be close to a downtown, regardless of when it was built. I forgot to snap a picture of it, however.

Next was Greensburg, which was the start of a trek through rolling hills reminiscent of the Driftless Region back home. Greensburg is home to one of the weirdest county courthouse attractions in the nation: There’s a tree sticking out of the bell tower, and it’s been growing since the 1870s. You’re not going to see that every day. Greensburg is also known as the Tree City because of this weird attraction. It reminded me of the phone booth on top of a building near the Logan County Courthouse in Lincoln, IL.


On a personally curious note, I had never seen a drive-up ice and water vending machine until visiting Greensburg. Apparently these things exist.

The road out of Greensburg took me through the small town of Napoleon. I was anxious to get to Milan, so I didn’t stay too long. It was a stop on the Underground Railroad, and also has a well-preserved bank building in its downtown: painted with street scenes of years ago, and preserving its old burglar alarm.

Old Milan Road (pictured at the top of this page) took me closer to Milan. The Nissan Altima that I’m driving (and renting) was almost wide enough to take up the entire road. Obviously I didn’t know that beforehand, but that only means that the road has retained its look from 75-100 years ago. The speed limit is slower and the hills and curves are more apparent. However, it’s called Old Milan Road because it takes you to the crossroads of Old Milan, the town before the current town, about a mile south.

You know you’ve made it to Milan when the road sign commemorating the 1954 Indiana State High School Basketball Champions is approaching – that, and the modern, cylindrical water tower with “Milan” in all caps descending vertically. This water tower, however, isn’t the one that was active in 1954 – that one still stands and is painted as needed on the west side of town.

Milan High School is the real life version of the Hickory team from the 1986 film “Hoosiers,” starring Gene Hackman and giving us fictional heroes such as Jimmy Chitwood (who, in reality, is based on Bobby Plump). The film is about the boys from a small town who overcome obstacles to face and defeat a state powerhouse to win the state championship. In reality, the Milan Indians did this in 1954 and beat Muncie Central in the title game.

I will write more about Milan in a separate entry, but there is a neat museum of artifacts about high school sports and the 1954 team in an old bank building. The display is impressive given that most things in other towns would likely be discarded or not preserved. You can also hear interviews with the team members of the ’54 squad.


After having lunch at an old tavern in town, I left Milan to head toward Cincinnati. There was one more stop along the way, a little burg called Mt. Sinai.

Those who know me well know that I like to have a little fun on these solo trips. Mt. Sinai – not this one – was the place where Moses received the 10 Commandments from God. So, with walking stick in hand, I did a short Moses impression and took a picture of it near a church. I had also “asked” for the five commandments that the Mel Brooks version of Moses dropped and broke in the film, “History of the World, Part 1.”

Descending on Indiana Route 350 toward Cincinnati, I arrived in Aurora, where the view was tremendous. Green mountains all around. And it was going to be that way for a while.

I did have one unfortunate situation happen while driving in Aurora. I filled up the car tank and accidentally got gas all over the body below the fuel door. This necessitated a car wash, pronto, and the one I pulled up into was one that I had never used before – the one with the wavy shams and foam cylindrical wheels. I didn’t understand the instructions, and the card reader was not working. Backing out became a problem because the curve was tight and I couldn’t maneuver it with this big of a car. I was stuck. I had to get out, and took the lesser of the two evils: going through the wash and its equipment as it stood there. Doing this is scary. Doing this in a rental car is even worse. I got out without a scratch, but not before a clerk flagged me down and wondered what I was doing. He was going to fix the credit card reader and I pulled back inside. He gave me instructions on how to park the car in neutral and let it move all on its own. On top of all of that, the wash sucked and the water was hard that it left streaks on the windows. At least my fuel mess was gone.

After that scare, I crossed into Ohio and entered Cincinnati. My only Cincinnati stop of the day was going to be Western Hills High School, the alma mater of baseball icons Pete Rose and Don Zimmer. Getting there was quite interesting, countless hills and countless curves on this ONE road through the northwest part of town. Driving through Cincinnati is like the noodles of Cincinnati chili.

Through all of that, I made it to Western Hills and got to sit in the stands of the school’s baseball diamond. Reds legend Pete Rose graduated from Western Hills in 1960, and Zimmer in 1949. The diamond structure has changed since their days with a more modern setup having been built in recent years. However, home plate is in the same location, and the high school building is still on the other side of the left field fence. I brought a couple of baseball cards to take along for selfies.


I was going to explore the rest of Cincinnati in Day 3, so I made my way to my hotel in the Kentucky suburb of Fort Mitchell. That meant going across the Ohio River on the double-decker I-71/75 bridge to Kentucky – a state that I had only been to once, and that was to do a U-turn near Cairo to “say I’ve been to Kentucky.” The view at the end of the bridge, looking at Covington was amazing! It felt like I was in a mountain range.

Day 2 came to a close, but not without issue. The room I was going to check into, another Super 8, did not have housekeeping done: Empty cans of Coke in the garbage, its box with one left unopened on the desk, a pair of slippers near the bed and the sheets undone. And this was discovered only after I had trouble getting the room key to work. Another room was promptly ordered, which was much better. This was a two-night stay, the cheapest hotel in suburban Cincinnati, and it left me thinking about hotel expenses.

As a solo traveler, I don’t require much: a comfortable bed, a working restroom; and maybe a working TV and maybe a working mini-fridge. I try to keep my hotel expenses at a minimum, because those can be costly come bookwork at trip’s end – Yes, I save receipts and track and double-check purchases at the end of the trips. Hotels like Holiday Inn, Radisson and Embassy are great for family stays (like we did as a family when I was young) because they have extra services and a big swimming pool. I don’t wish to pay for all of that because I don’t need it.

When I wrote about sports, there was a Super 8 in Washington, Illinois, near Peoria – where the Illinois state basketball tournament was. The Washington Super 8 was the cheapest “non-‘Meth’odist” hotel in the Peoria area, and it really wasn’t all that bad. However, over the years, and especially after the pandemic, I have come to be fed up with Super 8s. The Motel 6s may be another $20 more, but I think I will start converting to them (and did so beginning with Day 4 into 5). I am, however, a Wyndham Rewards member on top of all of this, so I’m not sure what to think heading to the next trip.

Yes, I rambled more about hotels than I did about Milan. However, it and a few other featured destinations will have their own entries on this website in the near future.

Not many miles driven for Day 3. To be continued.


Indiana, Cincinnati, Owensboro and more

Spring 2023 5-day, multi-state road trip

**Links will be posted over the course of April and May**

Link to Photo Galleries

Day 1 Travel Log

Day 2 Travel Log (you are here)

Day 3 Travel Log

Day 4 Travel Log

Day 5 Travel Log

Road Trip Stop: NCAA Hall of Champions, Indianapolis

Road Trip Stop: Milan ’54 Museum, Milan, IN

Road Trip Stop: William Howard Taft Boyhood Home, Cincinnati

Road Trip Stop: American Sign Museum, Cincinnati

Road Trip Stop: Bluegrass Music Hall of Fame, Owensboro, KY

Road Trip Stop: Ariston Cafe on Historic Route 66, Litchfield, IL

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