Eastern Kentucky Chili Bun Trail: Highland Park Drive In Williamsburg Kentucky

Highland Park Drive In in Williamsburg Kentucky

It’s a drive straight out of National Geographic.

Leaving Corbin, Kentucky and heading southbound toward Williamsburg on the “the old road” Hwy 26 offers a look into the new and old of Appalachia. There are solidly built brick homes, trailers mouldering into the earth, rushing creeks, burned down hulks of old houses, and tidy woodframe bungalows with pea gravel drives.

Before they built I-75, this was a main corridor, and featured dozens of businesses including the famous old Eveready Cafe.

Dana Wilson pauses during a busy shift at her family restaurant Highland Park Drive In in Williamsburg Kentucky

When I was a little kid I would beg my mom to let me spend the night with my buddy Bobby Reeves so we could sneak out of the house in the middle of the night and walk to the Eveready.

The joint was hopping with truck drivers, railroad men, coal miners, and steel workers all of them getting jaggedy on bottomless cups of black coffee whilst chainsmoking Pall Mall cigarettes.

One of the great regional delicacies in the U.S: an Eastern Kentucky chili bun

We’d sit in the haze til just before dawn ogling the waitresses in their polyester dresses, and eavesdropping on the grownups before sidling out the door and making our way home before Bobby’s mom figured out we were missing.

Nowadays 26 is a lot quieter, the Eveready is long-shuttered, and most of the businesses are boarded up. Just before you get into Williamsburg there’s an historical marker titled “First White Men Here” breaking down the arrival of pioneer Dr Thomas Walker way back in 1750. That’s it in the way of excitement.

The humble four burner cookstove at Highland Park Drive In in Williamsburg Kentucky

“Do y’all make the chili from scratch?”

Owner Dana Wilson, working as a carhop, pauses for just a moment and smiles in affirmation: “We sure do”

I ask after a chili bun, no dog, add onions and mustard, and make my way out of my car to take a few pictures.

Tom Wilson holds the family chili pot at his Highland Park Drive In in Williamsburg Kentucky

Highland Park Drive In was opened in 1970 by Gorman Wilson. The business had already been around for a few years but following his purchase Mr Wilson made it what it is today.

Sadly he passed away earlier this year but his son Tom and daughter-in-law Dana never missed a beat, and are still in the drive in six days a week turning out cheeseburgers, shakes, and of course their world-famous chili.

I beg my way into the kitchen where the lunch rush finds Tom and Dana working like a well-oiled machine hustling out the scratch chili, chuckwagons, BLTs, and fried baloney sandwiches. If you’ve got a sweet tooth the Wilsons could send a diabetic straight to the emergency room with hot fudge sundaes, banana splits, and a long list of milkshakes like pineapple, butterscotch, Reeses, and strawberry.

The griddle at Highland Park Drive In in Williamsburg Kentucky

You won’t leave hungry, and you won’t break the bank. Hell, a fat chili bun will only run you $2.04.

And that chili is some of the best I’ve found in eastern Kentucky. The grind of the pure beef is quite fine as is tradition. This is a mild chili with just a waft of pepper heat. If you like the four alarm style that sends you running to the bathroom in the middle of the night then keep on driving as this is not the fiery stuff that you used to find at the Fad Pool Hall in nearby Corbin.

A Heiner’s Bakery hot dog bun is the pillowy, white flour standard that is required for a genuine Eastern Kentucky Chili Bun Trail experience. Yellow, ballpark mustard and cold, chopped white onion completes the dish.

Lunch rush at Highland Park Drive In in Williamsburg Kentucky

Gorman Wilson’s chili recipe has stood the test of time. It’s paid house notes, bought automobiles, put clothes on backs, and kept the family fed for nearly 50 years. Tom Wilson pulls out a giant kettle “This is the same old chili pot my dad used from the 70s.”

It’s spotless. As is the kitchen.

During the busy summer months the Wilsons make three big pots a week. Once the fierce Kentucky winter sets in that output dips to two.

Highland Park Drive In
496 Hwy 25
Williamsburg, Kentucky

“Is chili the most popular item on the menu?”

Surprisingly it’s not. Chef Tom gives that accolade to the double bacon cheeseburger with the chili coming in a close second.

I silently fantasize about a double bacon cheeseburger with a heavy ladle of that chili as a garnish.

The Wilsons are busy handling the crowd of eaters so I say my goodbyes.


As I leave a man motions me over to a picnic table.

“There’s another really good chili spot right down the road apiece” he offers conspiratorially. I nod surreptitiously: “Tell me,” I whisper

He gives me the info like we’re two cold war spies in a smoky pub in Gdansk. I drift over towards my car and point south towards the tipsters spot.

Highland Park Drive In
496 Hwy 25
Williamsburg, Kentucky


Hours of operation
Always call ahead

Tom Wilson, owner and chili cook at Highland Park Drive In in Williamsburg Kentucky

About RL Reeves Jr

I'm a writer living and working in New Orleans, Louisiana.
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11 Responses to Eastern Kentucky Chili Bun Trail: Highland Park Drive In Williamsburg Kentucky

  1. Tammy says:

    They have the best banana splits

  2. Kimberly Griffith Thomas says:

    I love this place…..I use to eat there at least twice a week when I lived in Highland Park. Awesome people.

  3. judy meadows says:

    i am 64 yrs. old and this is the first place i worked at age 16

  4. Joan says:

    Love this!! Miss and love you too Dana!!

  5. RL Reeves Jr says:

    I’m getting one on my next visit. Hate that it’s 700 miles away. rl

  6. RL Reeves Jr says:

    The Wilsons definitely know the meaning of southern hospitality. rl

  7. Anthony Ellis says:

    Nice place to grab some good food at a reasonable price.

  8. Janet Bukovitz Fields says:

    Hamburgers, fries, milkshakes, BBQ… doesn’t get any better, right down to the ice in my Dr Pepper. Eat there every time I’m in town!!😊

  9. RL Reeves Jr says:

    I’d kill to have a place like Dana and Tom’s in New Orleans

  10. Theresa says:

    It’s a wonderful place when we go home for the family reunion on July we always try to get by there always food food and a decent price

  11. RL Reeves Jr says:

    It’s on my short list of places to visit when I hit the Eastern Kentucky Chili Bun Trail

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