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Home Lifestyle Travel

Jackson Purchase road trip filled with many quirks

Donna B Stinnett by Donna B Stinnett
November 12, 2026
in Travel
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Jackson Purchase road trip filled with many quirks

One of the many quirky stops in Western Kentucky’s Jackson Purchase: the Woolridge Monuments in Mayfield’s Maplewood Cemetery, where there are 18 life-size statues in the plot that were built for Colonel Henry G. Wooldridge, the only person actually buried in the plot. (Photo by Donna B. Stinnett)

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(This article first appeared in the November print edition of the Hendersonian.)

Sometimes you just need to change the scenery for a bit.

Especially if it’s Fall Break and it seems like everyone you know has vacated for the white sands of the Florida panhandle or Mickey’s Place.
We had 36 hours to spare, so just enough time for a quick road trip loop through the Jackson Purchase of Western Kentucky.

This was a time to seek out and enjoy “the little things.” Oddities is too strong a word. Let’s go with quirks.

We were armed with a homemade car game titled “Kentucky Road Trip Bingo: Western Kentucky Edition,” which had us on the lookout for such things as a coal barge, a train on a mural, a distillery, a barnyard of goats and 32 other items, the four of us hit the backroads.

Paducah flood wall murals
Our Ohio River neighbor to the west has made great use of their flood wall by using it as an art canvas.
In this UNESCO Creative City, the Dafford murals capture Paducah’s history from the days of indigenous people through the Atomic Age and beyond. The project began in 1996 and the first 20-panel timeline was finished in 2001. Another section was added in 2022.
It’s a beautiful piece of public art that can be visited any hour of the day or night.
Oh, and by the way, there’s a train on one of the murals.

Colorful place name
We needed to find a community that fit this bill for the bingo card, and we found them a-plenty in the Jackson Purchase.
But we aimed our sights on Monkey’s Eyebrow. There’s not a lot other than a sign that’s great for a selfie.
There were originally two Monkey’s Eyebrows, commonly known as Old Monkey and New Monkey. One was at the top of a small hill, the other at the bottom. There were stores at both locations. Today, there are no stores.
A common joke in the region is to provide directions to the city of Paducah by saying “it’s halfway between Monkey’s Eyebrow and Possum Trot (a community in Marshall County.)

Three states in three minutes
Alas, it would have taken only three minutes if there hadn’t been a construction delay. It was still pretty darn quick.
Just beyond Wickliffe in Ballard County, you can cross the Ohio River into Illinois just south of Cairo.
And then, you can immediately cross another U.S. 60 bridge into Missouri. Then turn around and come back across.
It’s pretty cool from this vantage point to see where our Ohio River flows into the mighty Mississippi. They are two completely different rivers in their nature.
But on either river, it was a very easy place to check off the coal barge on the bingo card.

A Civil War landmark
At Columbus, we found the “Gilbraltar of the West,” Columbus-Belmont State Park. The site served as a major Confederate fortification in 1861 and was the location of the Battle of Belmont, which was General Ulysses S. Grant’s first engagement. It also features a massive anchor and chain used in attempt to block Union gunboats on the river.
We found a campground for the bingo card.

A distillery operation on a barge
Ingram Distillery (yes, it’s part of the barge company we routinely see moving up and down the Ohio) has a theory that storing whiskey on one of their barges moored on the Mississippi (at Columbus) produces a unique product. Has to do with the “action” that the river movement causes within the barrels.
You can take a tour of that storage facility, going down into the barge. (Mind your step and watch your head.) And, the view at the Visitor’s Center on the bluff is spectacular.
Distillery on the bingo card: Check.

A city in two states
Henderson County shares a community with Webster County (Poole) and Fulton straddles the Kentucky-Tennessee border. The Tennessee side is called South Fulton, but it’s all one city.
Fulton (a railroad town that is an Amtrak stop for the “City of New Orleans” train) was once known as the “Banana Capital of the World” because 70 percent of the nation’s bananas were shipped through there on the railroad.
Right on the state line you’ll find a well-done boutique hotel called The Meadows. It’s a good base for visiting the beautiful Reelfoot Lake or shopping for fancy pageant and ballgown dresses across the street at Joann’s, which has dressed the stars.
Local drugstore on the bingo card: Check.

“The Strange Procession Which Never Moves”
In Mayfield’s Maplewood Cemetery, we found the Wooldrige Monuments. There are 18 life-size statues in the plot that were built for Colonel Henry G. Wooldridge, which is the only person actually buried in the plot. He wanted this treatment to commemorate family members and the other loved ones of his life. In addition to people, the monument includes a horse, a fox, a deer and two hound dogs, “Towhead” and “Bob.”
Sadly, the cemetery stop didn’t contribute to the bingo card challenge. If only the Wooldridge sculptor had included a goat.

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