Louisville, Kentucky, is, and probably always will be, the heart of bourbon country, so it’s the perfect place to begin and end an eight-day, six-state whirlwind whiskey road trip to discover not just Kentucky bourbon and Tennessee whiskey, but contributions from Virginia, Ohio, Indiana, and more as whiskey distilling booms across all 50 states. It goes without saying, but we’ll say it anyway: it’s especially important to drink responsibly throughout this itinerary and never drink and drive.
Day 1: Louisville, KY
Bourbon is best in this town, where you can base yourself for excursions to a few distilleries on the Bourbon Trail. Stop in Shelbyville, about 45 minutes from Louisville, and check out the Bulleit Distilling Co. Visitor Experience. A half hour from Shelbyville is Versailles, where you’ll want to stop to explore Woodford Reserve Distillery for a far more traditional approach to whiskey making. Stay at Vu Guesthouse, a boutique with mystique to spare.
Days 2 and 3: Lexington, KY
Visit the Old Pepper Distillery, where James E. Pepper is once again being distilled after the lot sat abandoned for more than 50 years. Now revitalized, it’s the centerpiece of the Lexington Distillery District, featuring 25 acres of shops, eateries, and plenty of spots to stop for additional sips. Don’t venture off without touring the distillery’s fascinating (small) history museum. With more than 400 horse farms in the city, Lexington is the “horse capital of the world,” so you may want to check out a stately site like Keeneland Race Course to enjoy the beautiful grounds, scope out some stellar horses, or catch a Thoroughbred race. It’s open daily to the public. Spend the night at Origin Lexington.
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Day 4: Bardstown, KY
Today’s goal is only about 60 miles southwest of Lexington, but it’s smack between two classic distilleries you won’t want to miss. On the way, just over a half hour from Lexington, Lawrenceburg is home to Wild Turkey Distillery, where the world’s longest-tenured master distiller continues to oversee whiskey traditions that predate Prohibition. You’ll also find Matthew McConaughey’s favorite bourbon, Longbranch, here (he created it). The tour and tasting will take one hour. Bardstown is more than a place to crash for the night. Depending on how early you get started today, you should be able to visit at least one or two of its main attractions, including the Oscar Getz Museum of Whiskey History,Women’s Civil War Museum, and My Old Kentucky Home mansion. There are even a couple of distilleries in town if you’re up for more tasting (you’re done driving for the day, so go for it).
Day 5: Mammoth Cave, KY
Start fairly early today and head to Mammoth Cave National Park, home of the world’s longest known cave system, just over an hour from Bardstown. Arrange a spelunking or hiking tour to explore on a cave tour (Cleveland Avenue is one of the best) and head to lunch at the Porky Pig Diner before or after your adventure. You can stay nearby or head to Nashville, about a 1½-hour drive away.
Days 6 and 7: Nashville, TN
You’ll trip over things to do in Nashville (hello, Grand Ole Opry and Honky Tonk Highway!), but make sure one of them is a visit to Nelson’s Green Brier Distillery. With a dramatic history including shipwreck and lost family fortune on the way to seeking the American dream, Charles Nelson went from soap maker to grocer to distiller, becoming one of the pioneers of whiskey bottling before Prohibition closed the business. Generations later, descendants rediscovered the distillery and relaunched the brand exactly 100 years after it closed. Stay on theme with dinner at Whiskey Kitchen. Alongside the city’s largest collection of whiskeys, you’ll find delish pub fare like the Fried Green Tomato BLT, Lowcountry Pulled Pork sandwich, and a city staple, Nashville Hot Fried Chicken. Slip into Nashville’s new urban style with a stay at Fieldhouse Jones in the city’s artsy East Nashville neighborhood.
Day 8: Bloomington, IN
It’s almost a five-hour drive to Bloomington from Nashville, but make a stop about two hours in to Abraham Lincoln Birthplace National Historic Park, the first memorial to Lincoln, or in Borden to Starlight Distillery at Huber’s Orchard, Winery & Vineyards, about an hour from the Abe Lincoln detour or three hours direct from Nashville. When in Bloomington, tour Fountain Square or Hoosier National Forest. In the evening, visit Bloomington’s first craft distillery, Cardinal Spirits, for dinner, drinks, and a tour. You’re halfway through your whirlwind whiskey odyssey now, so take a break to appreciate sips of Cardinal’s vodka, gin, or rum—these are the specialty here. Check in to the Showers Inn Bed & Breakfast for a cozy stay in the center of town.
Days 9 and 10: Indianapolis and Columbus, OH
Head north to Indianapolis before venturing east along Interstate 70 East for the majority of today’s shorter drive (four hours total). A stop in Indianapolis will keep the second leg just over 2½ hours. While in the capital city, stop by Westfork Whiskey Co. for smooth sips of distilled Indiana grains in the tasting room. Other options include checking out the Eiteljorg Museum of Native American and Western Art,White River Gardens,Kurt Vonnegut Museum and Library, and, of course, Indianapolis Motor Speedway. When you make it to Columbus, tour Middle West Spirits, where it’s all about appreciating the good life: one cofounder describes a sip here as an “everyday special occasion.” Try the ryes, including dark pumpernickel, and remember that bourbon doesn’t have to be made in Kentucky—it’s just a myth—so give it a go, perhaps in a cocktail at Service Bar, on-site. Stay at the Blackwell Inn.
Day 11: Purcellville, VA
Today’s drive is the longest of the trip clocking in at just over 6½ hours, traveling west into northeast Virginia. You may be surprised to learn that Virginia is the birthplace of American whiskey, but it’s true. Visit Catoctin Creek Distilling Company to tour the facility, try a whiskey flight, and snag a bottle of Virginia’s most awarded whiskey, Roundstone Rye, to take home. A tour and tasting combo here will take about an hour. You’re clearly in town for Catoctin Creek, but this is wine country, so you may want to check out one or two of the many surrounding wineries. For a less alcohol-centered activity, there aren’t many spots more charming than Blooming Hill Lavender Farm, open to the public for strolling and shopping. Springdale Village Inn is the bed-and-breakfast for you in Purcellville.
Days 12 and 13: Alexandria, VA and Maxwelton, WV
An hour east of Purcellville, stop at George Washington’s Distillery at Mount Vernon in Alexandria to tour a re-creation of one of the nation’s earliest large-scale whiskey distilleries, and one of the most profitable ventures on Washington’s estate. Sample one last taste of Virginia whiskey at KO Distilling in Manassas, about 45 minutes west of Alexandria. Try a flight of Bare Knuckle whiskeys, including straight bourbon, wheat, and rye, from this relative newcomer to the craft distilling scene. Have lunch in Manassas before the final 3½-hour haul to Maxwelton. At the Bone BBQ, you’ll find pulled pork, hickory-smoked chicken, smoked turkey, brisket, and more served with sweet-potato fries and mac ‘n’ cheese. Finally, arrive in Maxwelton. Get a taste of Appalachian whiskey at Smooth Ambler Spirits in the West Virginia mountains, where they believe their clean water, crisp air, and ideal climate produce some of the country’s top spirits.
Day 14: Lousiville, KY
Make the five-hour drive back to Louisville, which you can break up by stopping in Charleston, about 3½ hours into your drive. When you make it to Louisville, celebrate: there is a ton of whiskey and bourbon to be had here. The great news is you can walk to many of the distilleries (or their outposts) in town, so you can taste a little more enthusiastically than when you were driving. Three spots you must hit are Old Forester Distilling Co., home of America’s first bottled bourbon; Angel’s Envy Distillery, finished in port wine casks; and Rabbit Hole Distillery, a hypermodern outfit with an art collection as covetable as its spirits. Have one last carnivorous feast at Steak & Bourbon where, as you’d guess, large slabs of beef and an even larger bourbon collection (about 70 varieties) are the specialties.