4 essential stops on your Eastern Kentucky Road Trip. Yes, there is bourbon

Throughout the 17th and 18th centuries, wealthy young aristocrats in Europe would embark on a “grand tour” where they’d sample the art, history, culture – and the alcohol – of multiple countries.

I couldn’t get the idea of a “grand tour” out of my mind as we toured Eastern Kentucky. Every stop was so rich with heritage, history, butter-filled recipes and bourbon.

So much bourbon.

So where should you stop on your “grand tour” of southern Appalachia? Which “museum” was the opposite of what you’d expect, and where can you find a mind-blowing natural phenomenon that only occurs in Kentucky and Zimbabwe?

Let’s explore four essential stops on your Eastern Kentucky road trip. 

Bluegrass Heritage and Brisket Fries in Winchester

With a name like Winchester, Kentucky, you’d expect this small, 20,000-person town to deliver a hearty dose of raw Americana. You know, things like succulent homemade brisket, a charming antique theater and a museum in a refurbished Victorian mansion. 

Check, check, check. 

As a first stop, I’d highly recommend the Bluegrass Heritage Museum which – contrary to my naive assumption – isn’t about music. Instead, it’s packed with antiques that tell the intimate story of numerous local families, from veterans on both sides of the Civil War to a survivor of Auschwitz who immigrated to Winchester and found an embrace in the local community. 

Once you’re feeling peckish you can head down Main Street to Smokin’ Howards Sports Bar and Grill: a charmingly simple BBQ joint beloved for its family recipes. Along with a delightfully moist pork sandwich, indulge yourself in a shameful amount of brisket fries as an appetizer. We did, and somehow, we lived to tell the tale. 

Finally, before you depart Winchester it’s worth peeking your head into Leeds Center for the Arts. Located right across Main Street from Smokin’ Howards, Leeds traces back to 1925 and still features its original seating. If you have the time, stay the night and see a show. 

Boone Tavern and Darn Fine Spoonbread in Berea

Berea College and the surrounding town of Berea have the most symbiotic relationship of any college/college town I’ve seen. Students of the four-year, non-profit university are required to work local jobs in exchange for free tuition, and many end up settling in Berea post-graduation to enrich the town even further. 

Oh, and Berea College was the first college in the South to be coeducationally and racially integrated. 

The net result is a ~15,000-person town exuding what I can only describe as “relentlessly positive vibes.” There’s a pervasive sense of calm and welcome in Berea, making it the perfect place for a chill/rest day on your Eastern Kentucky road trip. 

As for lodgings, I enthusiastically recommend the cozy and historic Boone Tavern. With nightly rates starting under $100, Boone Tavern features the best breakfast and second-best dinner I had in all of Kentucky – largely thanks to locally sourced ingredients from (you guessed it) current and former students. 

Dinner at Boone Tavern Restaurant starts with a hearty serving of spoonbread, a fluffy Southern cornbread dish that may look tough and crusty from the outside – but is soft enough to cut and eat with a spoon (hence the name). 

If you’re starting to feel a bit heavy and could use a pick-me-up, be sure to visit Nick in the adjoining Frost Café. He made me the best chai I’ve had outside India. 

Pinball and Farm-to-Table Delights in Corbin

As a kid, the first thing they teach you about museums is that you can “look, but don’t touch.” So when I heard we’d be visiting a pinball museum, I slid a 5-Hour Energy into my pocket out of fear that I’d fall asleep. 

Little did I know that the Pinball Museum of Corbin is the absolute best kind of museum -–one where you’re encouraged to touch absolutely everything, and the historical context is there if you’re interested in learning more. 

I vastly underestimated how much fun I’d have working my way down the aisles and sampling Elton John pinball, Iron Maiden pinball and my personal favorite: John Wick pinball. With an MSRP of roughly $10,000, each of these machines is a carefully engineered love letter to wealthy, diehard fans of the subject matter – so you can imagine how special each one feels to play. 

Case in point, when I set the high daily score in Guns N’ Roses pinball, the machine asked me to smile for a picture – and then superimposed me on a photo onstage with Slash (although sadly, I didn’t snap a pic in time). 

If you’re a fan of pinball, pop culture and/or any sort of competitive activity with your travel mate(s), the Pinball Museum of Corbin is worth the humble $18 price of admission. 

Plus, it’s right across the street from the #1 best dinner I had in all of Kentucky, courtesy of The Wrigley.

As much as I loved Boone Tavern for its delicious spoonbread and student-made ingredients, I can’t deny that The Wrigley supplied the best overall meal I’ve had in Kentucky. 

I didn’t make it easy on them, either. In a vain attempt to find a weak link on the menu, I ordered the salmon, birria tacos and a giant pretzel with beer cheese: three dishes from three separate continents. Alas, I was impressed by every bite. 

“Moonbows” at Cumberland Falls State Resort Park

I won’t beat around the bush; if you can spend at least one night of your road trip in DuPont Lodge at Cumberland Falls State Resort Park, you’ll get to wake up to this view:

And believe it or not, that’s not even the best – or even second-best – view in the whole park. 

Here’s #2, a view of the Cumberland Falls waterfall itself, aka “the Niagara Falls of the South.”  

Sadly, I couldn’t capture #1 on my phone because a) it’s a temporary phenomenon that didn’t occur while I was there and b) it’s virtually impossible to capture on camera anyways. 

It’s called a “moonbow,” aka a rainbow that only appears at night. Moonbows are so rare that there are only two places on earth where they appear on a consistent, predictable schedule: Victoria Falls in Zimbabwe and Cumberland Falls in the U.S. 

As mentioned, they’re also extremely difficult to photograph for a variety of obvious reasons. Even still, I found a photographer on Instagram who did a pretty impressive job: 

That about wraps up my list of the four essential stops on any Eastern Kentucky road trip. Honorable mentions include: 

• Hatfields and McCoys tour and Chirico’s Ristorante in Pikeville.
• Pauley Hollow Distillery in Forest Hills.
• Creative Coffees and the Ale-8-One Bottling Co in Winchester.
• Big South Fork Scenic Railway Train Ride in Stearns.

Did we miss any? Let us know in the comments, and for more ways to maximize your next travel adventure, be sure to subscribe to The Travel 100. 

– Chris Butsch, Contributor