I Biked 175 Miles Through the Kentucky Bourbon Trail. It's the Greatest Whiskey Experience on Two Wheels

The thing about drinking an old-fashioned at 10 a.m. is it’s easy to convince yourself to have another, even if you need to pedal your bike 65 miles to get it. I’m sitting with three friends in a trendy Louisville bar tucked into the back of a leather goods shop (that’s a thing here), rattling the ice cube in the bottom of my glass and contemplating our next move. It’s tempting to stay, but our bicycles and the open road are calling—and I’m getting ahead of myself.

We’re riding a slice of the Kentucky Bourbon Trail, a 300-mile route that links dozens of distilleries together through the Bluegrass State. People drive the Bourbon Trail all the time, but I convinced my buddies we should knock out more than half of it on road bikes, pedaling to distilleries and cocktail bars while testing our mettle on lonely backcountry roads. We’ll ride 175 miles over three days, from Bardstown to Louisville to Frankfort, then back to Bardstown.

It’s a bold attempt, but we’re all in our 40s and know the window for this sort of adventure is shrinking as we cruise through mid-life. We’re giddy to push ourselves and see what we can find on two wheels.

Bourbon & Baby Jesus in Bardstown

Our trip begins in Bardstown, “Bourbon Capital of the World,” where heavy hitters like Heaven Hill, Willett, and Barton have distilleries, as well as smaller operations like Preservation and Lux Row. We spend our first evening pedaling around town, bouncing from Heaven Hill to Neat Bourbon Bar & Bottle Shop—known for its reasonably priced pours of high-end whiskey—where a statue of Mother Mary and Baby Jesus looks down on us. It’s a shakeout ride to test our bikes and livers. We finish the night with a tasting at the new Trail Hotel, an upscale boutique inn that’s leaning heavily into the area’s bourbon pedigree. It even has an IV therapy spa designed to ease hangovers, and a cryogenic tank that supposedly helps boost recovery. It’s enticing, considering the athletic feat ahead of us.

It’s important you know none of us trained for this ride. The most prep we put in was a long text chain discussing how many outfits we could pack. We were lured in by the bourbon, and it’s only now sinking in just how far we’ll have to ride to earn it. But is there a better way to convince yourself you’re still in your prime than tackling an endeavor that’s just out of reach? I’d argue it’s better than buying a convertible or having an affair with a barista.

The Trail’s Bourbon Butler (yes, that’s a thing) runs our tasting in a speakeasy hidden behind a painting in the hallway—like something out of Scooby-Doo—and we work our way through three whiskeys. The stand-out is a 9-year Old Fitzgerald in a decanter that’s rich, buttery, and sets the tone for the trip. We’re going to work hard on our bikes, but there will be delights and rewards at the end of each ride.

All four of us spent our younger years as dirtbags to varying degrees, so it can be hard to admit we like nice things now. But it’s true. I insist on only playing with custom-fit golf clubs. My friend Kevin makes his own corn tortillas from scratch, because there’s no substitute. Hartwell often wears a captain’s hat seeing as he recently bought a boat. Dunbar has run out of room in his driveway because he can’t stop buying vehicles.

“What would your younger self think of your current self?” Kevin asks as we move from the whiskey tasting into the hotel’s posh golf simulator room.

It’s a good question that will follow us throughout this entire whiskey-soaked journey. On the one hand, younger me would be psyched that 49-year-old me is riding 175 miles to drink bourbon. On the other hand, I own a lot of button-down shirts now. As we ride, the confessions ramble out. Dunbar admits he has a thing for Martha Stewart.

“She’s a badass!” he tells us with sobering conviction, as we huddle on the side of the road searching Google Maps for a suitable bypass of a dangerous section of highway. I suspect more admissions will come. We’re spending eight hours a day in the saddle together, after all.

Leather & Lollygagging in Louisville

The first full day of riding has us pedaling from Bardstown to Louisville on busy highways. The constant barrage of 18 wheelers is harrowing, like swimming with great white sharks; we’re not at the top of the food chain. I appreciate the lesson in humility.

There are beautiful moments, though, like a side road that pops out of a corn field and meanders past rickhouses; and an impromptu stop at Coxs Creek Distilling Company, a two-room shop that’s putting out fun spirits, from well-aged bourbons to a lightly aged agave. It rivals any high-end tequila I’ve had, and I make a note to buy a bottle later. Space is too limited now because all of our gear is crammed into frame packs, seat bags, or handlebar stuffsacks. I want my kit to be as light as possible for the rolling hills of Kentucky. Souvenirs can wait.

For lunch, we eat ice cream sandwiches and beef jerky at a gas station, and wash it down with ice-cold Modelos at a Mexican tienda because, y’know, hydration is key. We end the ride with a dip in our swanky hotel pool, then stroll Louisville’s hipster neighborhood Butchertown on foot, grabbing old-fashioneds and amazing bibimbap at Nami, a Korean steakhouse, before finding ourselves in the bleachers watching the minor league Louisville Bats. A baseball game wasn’t on our agenda, but Hartwell points out it would be rude not to stop for a beer. We’re nothing if not polite.

Younger me would be happy with older me’s decision-making here, and that same thought process leads us to Clayton & Crume on our second day of riding. It’s among Louisville’s finest leather shops, rife with belts, wallets, and boxing gloves. Make your way around the corner and you’ll find a mustachioed bartender slinging bourbon- and rye-centric cocktails. It’s very Louisville. Perhaps less so is a group of men with helmets still strapped under their chins drinking bourbon for breakfast.

We’re road-weary from yesterday’s effort, where we spent most of the day hugging the shoulder on a highway while semis nuzzled too close for comfort. And yet we’re excited about the 60+ miles of unknown pavement ahead of us. Maybe it’s the bourbon?

Fatigue & Fulfillment in Frankfort 

The route to Frankfort is beautiful—undulating roads through small farms lined with black fences—but it’s hard and I regret not training. Fortunately, drinking copious amounts of sweet tea helps combat the cramping in my legs. I fill my water bottles with the Southern delicacy at a diner sandwiched between corn farms and decide sweet tea is just Gatorade without the marketing hype. Also, cocktails have electrolytes, right? Right.

The final leg of our second day is dramatic. We drop three miles through a shaded canyon with limestone walls rising from the side of the road. At the end is up-and-coming Frankfort, the third smallest capital city in the U.S. We stay at The Delegate Hotel, a new upscale boutique property with what might be the best food in all of Kentucky at its restaurant, Cypress and Oak. Its signature barrel-aged old-fashioned manages to elevate the humble Benchmark Bottled-in-Bond into something delicious, too. The cocktails at the House of Commons downtown are even better, so we linger in the beautiful bar, perusing a shelf full of books while discussing the art of dueling, which, according to multiple historic markers we’ve passed, was the primary way to settle a dispute in Kentucky back in the day.

“Dueling was so prevalent in the 1800s, the South Carolina governor wrote an official rule book,” Dunbar says. (No, he’s not reading a plaque; he just reads a lot about duels—hence acting as our de facto armchair expert.) “Slow and steady is the key,” he says. “You get one shot. You don’t want to fire first. You want to fire best.”

I feel like that advice could be applied to riding 175 miles of the Kentucky Bourbon Trail, too. Slow and steady is the way. 

The riding continues to improve as we move through the Trail. And the final day, a 70-mile push from Frankfort to Bardstown, is nothing short of gorgeous. We’re able to avoid the highways and roll through farms divided by dry stack stone walls. It’s here I decide bikes are the perfect form of transportation. They’re fast enough to cover miles efficiently, but slow enough to allow you to truly absorb the landscape. Horses graze in pastures and dogs chase us from their yards as Wild Turkey beckons us closer.

The visitor center is a marvel that’s modeled after Kentucky tobacco barns. Its chevron-patterned upper level and giant glass wall bathe the space in golden light, evoking a holy experience not dissimilar to a church. Except this church has whiskey tastings, a bar that makes incredible Boulevardiers, and is perched dramatically on a bluff overlooking the Kentucky River.

It’s nothing but farmland after Wild Turkey, and only one person yells, “Assholes!” at us while speeding by in a car. For the most part, Kentuckians have been warm and curious. At a gas station, a farmer looked over our bikes and asked what we were doing. When we told him, he shook his head and said, “Hell, if you’re that bored, I can give you something to do.”

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We roll through Bloomfield, a tiny two-street town that’s so picture-perfect we feel compelled to stop at its solitary watering hole, Ernie’s Tavern, which has an over-the-top nostalgic vibe complete with an old-school soda fountain and bowling alley. We bowl in our bike shoes before tackling the last leg of the trip.

Across the street from the bar, there’s one of those large chalkboards with the “Before I Die, I Want to…” prompt. It’s cheesy, but the question hits home as you get older, so I scribble “Finish this ride.” It’s not profound, but it’s concrete, and it seems like an honest way to start answering that question.

Bike 175 miles through Bourbon Country. Yeah, younger me would be OK with that answer.

This article appeared in Men’s Journal’s fall Whiskey Special issue.