Road Trips

Where to Find the Bluegrass State’s Best Sips on a Kentucky Bourbon Trail Road Trip

Take a journey along Kentucky’s famed Bourbon Trail and experience the best of the state’s distilleries. (All Photos: Kristin Luna)

Bourbon has become synonymous with Kentucky, a distinction the Bluegrass State wears like a badge of honor. In celebration of the statewide industry, the Kentucky Bourbon Trail was established in 1999 and currently comprises nine distilleries. You can also visit 13 craft distilleries on the five-year-old Kentucky Bourbon Trail Craft Tour.

The Kentucky Distillers Association estimates that more than one million visitors stopped at distilleries along the trail in 2016 alone. Want to follow in their footsteps? Use this spirited itinerary as your guide.

At more than 100 miles the route would take a mere three hours if driven straight through. However, with the sweeping, bucolic landscape of Horse Country — not to mention a number of strategic stops for food and adult beverages — it’s best suited for a long weekend. (Drink responsibly, have a designated driver, and cheers!)

kentucky bourbon trail
Kentucky is horse country.

Start: Louisville

The gateway to the Bourbon Trail, Louisville is Kentucky’s largest city and a great place to whet your palate with a craft experience or two. Have an Old-Fashioned — Louisville’s official cocktail of choice — at the Pendennis Club, where the drink is said to have originated. Then get to work filling out your Urban Bourbon Trail passport, which you can pick up at the visitor’s center or any of the participating stops.

Louisville’s Whiskey Row, a thriving distillery district through the 1920s, has recently seen a revitalization with the addition of new residents. Kentucky Peerless Distilling Co., once the second-largest distillery in the state, reopened in 2015 after shuttering in 1917. And Angel’s Envy opened its doors in fall 2016.

On the food side of the equation, you’ll have your pick of top-notch restaurants over in the “NuLu” district along East Market Street, where the restaurant scene is positively hopping. Start with a cocktail at Rye before moving onto Galaxie for an out-of-this-world dining experience and live music at the adjoining OUTERspace venue.

Late night you’ll want to claim a pingpong table and a grass-covered bench at Garage Bar for a nightcap coupled with a little friendly competition.

Stop 1: Bardstown

Distance from Louisville: 41 miles

Drive time from Louisville: 55 minutes

Though not even an hour from Louisville, a visit to Bardstown feels akin to time travel, with its stately Victorian houses, horse-drawn carriages and old-fashioned saloons, some dating back to the 18th century.

Founded in 1780, the approximately 11,000-resident town is touted as the “Bourbon Capital of the World.” Its most prominent resident is Heaven Hill Distillery, though a visit to Willett provides a more intimate experience, with a family-owned operation and location along a natural spring.

Stop 2: Versailles

Distance from Bardstown: 48 miles

Experience a tasting at Woodford Reserve.

Versailles (pronounced “ver-say-elles”) has long been integral to the thoroughbred industry, but Woodford Reserve put it on the global map. The distillery also offers one of the most polished tour and tasting experiences this side of the trail. And the approach to the grounds — located among rolling hills and horse farms aplenty — is breathtaking, too.

But the biggest buzz at the moment surrounds Castle & Key Distillery, which is just three miles down the road from Versailles and slated to debut in late summer 2017.

kentucky bourbon trail
The Castle & Key makes for a tasty — and intriguing — stop.

Helmed by Marianne Barnes, formerly of Woodford and the state’s first female master distiller since Prohibition, Castle & Key revived an old limestone castle that housed Old Taylor Distillery in the 1800s.

Though it will be years until her bourbon is ready to consume due to the aging process, in the meantime Barnes is using the on-site botanical trail to whip up some smooth gin for sipping.

End: Lexington

Distance from Versailles: 13.5 miles

In eastern Kentucky, Lexington provides a very different scene than that of Louisville, even though just 80 miles of interstate separate the two.

Home to the annual Keeneland horse races in April and October — a “Lex” staple since 1936 — the state’s second-largest city also lays claim to the University of Kentucky, lending it a college-town feel and a hearty dose of character.

That also means that, distilleries aside (the town has five), there’s a growing brewery scene, thanks in part to the evolution of the Brewgrass Trail.

kentucky bourbon trail
Need a whiskey break? Hit up a brewery.

With punny names like Shotgun Wedding (a dark-brown ale), Country Boy Brewing is a fan favorite, though there’s rarely an empty seat at West Sixth Brewing, Mirror Twin Brewing Co. or Ethereal Brewing on weekends either.

Bourbon aficionados occupy the plush booths at Belle’s Cocktail House, where more than 100 bourbons populate the playlist.

Foodies flock to the concept-driven restaurants cropping up around town, like Country Club, which specializes in smoked meats. And urban art lovers dig the Lexington Mural Project with its more than two dozen installations, like a 60-foot-tall, rainbow-colored depiction of President Abraham Lincoln on the back of The Kentucky Theatre.