The Best Road Trips in America

The Bourbon Country Tour

The Bourbon Country Tour
PHOTO: Jesse Wong
The Bourbon Country Tour
The Best Road Trips in America
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The Bourbon Country Tour

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Bourbon doesn’t always come from Kentucky, but it does originate in the United States and is the country’s only federally legislated spirit, making it one of the most beloved whiskies in America and the centerpiece of any whiskey trail trip.

At A Glance

STARTLouisville, KentuckyENDLouisville, KentuckyMILES
8 nightsstates
Indiana, Kentucky, Ohio, Tennessee, Virginia, West Virginia

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. There’s plenty of time built into this itinerary to linger at each distillery, and remember that these are tastings, not ragers, so sip and savor thoughtfully. ...Read More

The Bourbon Country Tour
PHOTO: Jesse Wong

At A Glance

STARTLouisville, KentuckyENDLouisville, KentuckyMILES
8 nightsstates
Indiana, Kentucky, Ohio, Tennessee, Virginia, West Virginia

The Itinerary

Louisville to Lexington, Kentucky STOP 1  Louisville to Lexington
Lexington to Bardstown, Kentucky STOP 2  Lexington to Bardstown
Bardstown to Nashville, Tennessee STOP 3  Bardstown to Nashville
Nashville to Bloomington, Indiana STOP 4  Nashville to Bloomington
Bloomington to Columbus, Ohio STOP 5  Bloomington to Columbus
Columbus to Purcellville, Virginia STOP 6  Columbus to Purcellville
Purcellville to Maxwelton, West Virginia STOP 7  Purcellville to Maxwelton
Maxwelton to Louisville, Kentucky STOP 8  Maxwelton to Louisville

Louisville to Lexington, Kentucky

1 h 40 m
85 mi
Route: Today’s drive is a simple start and the shortest leg of the trip, traveling an easy 80 miles eastward. Don’t get too late of a start, though: You’ll want plenty of time at the three distilleries along the way.

Town: Shelbyville, Kentucky. Stop in Shelbyville, about 45 minutes from Louisville, and check out the Bulleit Distilling Co. Visitor Experience. Here, where sustainability and technology are driving forces behind the production of the brand’s traditional rye recipe, you’ll find one of the more modern facilities on your journey and catch a shiny glimmer of the future of American whiskey. The tour and tasting will take an hour.

Town: Versailles, Kentucky. 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. Bourbon was first made on this property in 1812, and you’ll feel (and taste) the history everywhere. The tour and tasting will take an hour.

Eat: Snag lunch at Glenn’s Creek Café at the Woodford Reserve Distillery, where the chef-in-residence whips up distillery-inspired favorites, like Bourbon Trail Chili (made-from-scratch cornbread include) or the slow-cooked Bourbon Barbecue Pulled Pork Sammich.

Do: 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, where you’ll learn that the Old Fashioned was allegedly invented for Colonel Pepper, himself, during a visit to New York City’s Waldorf Astoria Hotel. Naturally, it’s the only cocktail served here today. 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 some stellar horses, or catch a Thoroughbred race. It’s open daily to the public.

Eat: Grab a few slices of New York-style pizza at Goodfellas Pizzeria in the Distillery District, just a few steps from Old Pepper Distillery. There’s plenty of outdoor seating (and a bocce ball court), but be sure to poke around the industrial interior for a bit of gawking before chowing down if you’ll be dining al fresco. Save room for dessert around the corner at Crank & Boom Ice Cream Lounge, where local ingredients are churned into small-batch flavors like Kentucky Blackberry & Buttermilk and Bourbon & Honey. Feel free to upgrade to a Spiked Scoop.

Stay: Spend the night at Origin Lexington, where stylish rooms feature accents of moss green, soft gray, and leathery brown below sexy black ceilings. If you won’t make it to the 24-hour fitness center, have a free yoga kit (mat, block, and strap) sent to your room.

Breakfast: Get ready for Day 2 with breakfast at Josie’s in the Chevy Chase neighborhood of Lexington. This breakfast-all-day spot has a lighter fare, like egg white omelets and organic granola, for the health-conscious and gluttonous, heavier fare, like sausage gravy and biscuits, for those setting a solid foundation for the day’s whiskey consumption.


Lexington to Bardstown, Kentucky

2 h 45 m
120 mi
Route: 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 so you’ll need to shun the straight line and embrace a somewhat circuitous route just this once.

Town: Lawrenceburg, Kentucky. 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.

Photo Op: Just outside the entrance of Wild Turkey is a giant mural of, well . . . a wild turkey (you’ll recognize it from the bottle), and it’s a perfect spot for an amusing pose to commemorate your wild whiskey wanderlust.

Town: Loretto, Kentucky. An hour from Wild Turkey, you’ll hit Maker’s Mark Distillery in the town of Loretto. Try your hand at bottle dipping to seal your own souvenir in the brand’s signature red wax after exploring the natural beauty of this sprawling distillery, including its own water source in the form of a 10-acre limestone-filtered lake. (Good to Know: Limestone filtration is why Kentucky believes it has the best bourbon!) The tour and tasting will take an hour.

Eat: Have lunch at Star Hill Provisions at Maker’s Mark Distillery. The chef-in-residence prepares seasonal menus of local Kentucky ingredients with hearty sandwiches, like Golden Reserve Meatloaf on ciabatta, and flavorful salads, like Whisky Creek with roasted butternut squash, sunflower seeds, and walnuts in a maple bourbon vinaigrette. The star of the menu is the Maker’s and Ale-8-One Slushie, ideal as dessert.

Town: Clermont, Kentucky. Stop in Clermont to tour the home of the world’s best-selling whiskey at Jim Beam American Stillhouse. Jim Beam is aged twice as long as the legal requirement for bourbon, and the tour lasts a little longer than your typical distillery walkthrough, too, so you may have time to safely snag an extra sip at the Jim Beam Bourbon Bar and linger a little at your last stop of the day. The tour and tasting take 90 minutes.

Do: 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 distilleries in town if you’re up for more tasting (you’re done driving for the day, so go for it).

Eat: Embrace Kentucky cuisine with dinner at Kurtz Restaurant, where family recipes have been served in this historic house since 1937. Start with Kentucky country ham or skillet-fried chicken, but save room for sampling the scrumptious pies and cobblers after.

Stay: Book a room in The Talbott Inn for a convenient stay in the center of downtown Bardstown, steps from the quaint town’s restaurants and shops. You’ll find modern rooms in a historic 1913 building and you can’t beat the price or location. If you’re up for some potential spook factor, you could check into the neighboring Talbott Tavern bed and breakfast, built in 1779, instead. Here, you’ll also find the world’s oldest bourbon bar.

Breakfast: Day 3 comes with considerably more drive time, so pop into Fresh for a to-go breakfast. Grab some Good Folks coffee and a big ol’ pastry or two from this zero-waste kitchen with a locally-sourced menu that changes weekly (and sometimes daily).


Bardstown to Nashville, Tennessee

5 h
300 mi
Route: Start fairly early today as the first leg of this journey takes you 3.5 hours south to your first stop before about-facing northward toward Nashville.

Nature: If you can pull yourself out of bed even earlier, a slight detour of about 15 minutes in each direction will bring you to Mammoth Cave National Park, home of the world’s longest known cave system, just over an hour from Bardstown. The visitor center opens at 8 a.m. but if you want to spend the recommended 3 hours exploring, you may need to cut a distillery from your day.

Town: Lynchburg, Tennessee. Leave Kentucky bourbon behind (for now) and move on to Tennessee whiskey today with a tour of Jack Daniel’s Distillery in Lynchburg. Themed tours range from 70 to 90 minutes for more traditional experiences and 3 hours for a filling tour that culminates in a country meal.

Eat: Have lunch in town at Miss Mary Bobo’s where Southern hospitality has been the hallmark of every hearty meal since Miss Mary Bobo opened her kitchen in 1908 and ran it for more than 60 years. Now owned by the Jack Daniel’s Distillery, the family-style restaurant has expanded to nine dining rooms serving more than 200 hungry patrons daily so you’ll want to make reservations for this one.

Town: Shelbyville, Tennessee. Relearn your whiskey history with a visit to Nearest Green Distillery in Shelbyville, where Uncle Nearest Premium Whiskey is produced. Uncle Nearest was the world’s first African-American master distiller and the man who taught a young Jack Daniel to filter his whiskey through sugar maple charcoal. The tour takes 90 minutes.

Do: You’ll trip over things to do in Nashville, 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 soapmaker 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. The tour and tasting will take about 45 minutes.

Eat: 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, Low Country Pulled Pork Sandwich, and a city staple, Nashville Hot Fried Chicken.

Stay: Slip into Nashville’s new urban style with a stay at Fieldhouse Jones in the city’s artsy East Nashville neighborhood. Uniquely designed accommodations range from traditional and deluxe rooms and suites to legitimately cool bunk bed combos, and the public spaces are a social media star’s dream come true.

Breakfast: Try something new this morning. Head to Yeast Nashville and order a tongue-twisting Tex-Czech Kolache with your morning tea. Traditional Czech kolaches are like super thick danishes of brioche-y dough filled with fruit, poppyseed, or cheese, but a Tex-Czech version embraces the tradition of 19th-century Texas Czechs who started stuffing them with meat.


Nashville to Bloomington, Indiana

4 h 40 m
275 mi
Route: Head north on I-65 N through Kentucky and into Indiana. It’s a long one, but a fairly direct route today.

Detour: Just under two hours into your drive, American history buffs will want to hop off I-65 in Kentucky for a 20-minute detour to Abraham Lincoln Birthplace National Historic Park. The first memorial to Lincoln, 56 steps lead up the knoll where he was born to commemorate his 56 years of life, and a humble replica of his one-room cabin can be found within the stately memorial at the top.

Town: Borden, Indiana. Pay a visit to Starlight Distillery at Huber’s Orchard, Winery & Vineyards, about an hour from the Abe Lincoln detour or 3 hours direct from Nashville. While originally launched to distill brandies from the vineyards’ grapes, Starlight also produces a few single barrel bourbons and ryes, and even a blackberry whiskey worth a taste. The distillery tour and tasting will take just 30 minutes, so you may want to tack on the 30-minute wine tour and tasting, too, for a broader understanding of the whole operation.

Eat: While road trippin’ through small-town USA, have an all-American lunch of a burger and fries at Norma Jean’s Ice Cream during your stop in Borden. Order from the window and chow down at the creekside picnic tables. You should finish this meal with some scoops of ice cream, and are encouraged to venture into flavors like Fat Elvis, Zanzibar Chocolate, and Orange Pineapple.

Do: Just an hour south of Indianapolis, Bloomington is a quaint city near Lake Monroe with equal helpings of nature and culture. Downtown has plenty of shops and galleries, like the popular Fountain Square shop collective and the I Fell community art center with studios, shops, and a bakery. Check out the Eskenazi Museum of Art and the Wylie House Museum for indoor activities, or head to McCormick’s Creek State Park or Hoosier National Forest for outdoor time.

Eat: 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. For dinner, try the Truffle Chicken with mashed potatoes or the Salmon Breeze with broccolini and maitake mushrooms.

Stay: Check in to the Showers Inn Bed & Breakfast for a cozy stay in the center of town. The historic Showers-Graham house is outfitted with modern conveniences and upscale amenities at reasonable rates with complimentary parking.

Breakfast: Take advantage of the included breakfast buffet at the Showers Inn. In addition to the standards like fruit, yogurt, and cereal, you’ll find house-made specialties like corned beef hash and poached eggs, spinach and Gruyère strata, and lemon poppyseed pound cake.


Bloomington to Columbus, Ohio

3 h 50 m
230 mi
Route: Head north to Indianapolis before venturing east along I-70 E for the majority of today’s shorter drive. A stop in Indianapolis will keep the second leg just over 2.5 hours, and there are no other major stops along the way so feel free to take a later start and aim to be in Indy for lunch.

Town: Indianapolis, Indiana. This is your sole stop before Columbus and with only 2.5 hours to go, you have plenty of time to explore Indiana’s capital city. If you can’t wait until evening for today’s dose of whiskey, 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.

Eat: It may not look like much from the outside, but if you ask a local for a lunch recommendation you’ll probably be directed to Lockerbie Pub. You’ll find everything from fried pickles to burgers at this inexpensive dive, but the breaded tenderloins are what keep business strong (well, that and the beer).

Do: If you’ve had enough of museums from earlier today, check out outdoor Columbus by toddling around German Village, taking pics in Topiary Park or Columbus Park of Roses, or admiring nature at Hayden Falls Park. Toward the end of your exploration, tour Middle West Spirits, where it’s all about appreciating the good life, and one co-founder 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, onsite.

Eat: Service Bar is the spot to stay for dinner, whether you went for that bourbon cocktail after your tour or not. Expect serious upgrades to familiar plates, like Crispy Ribs with fried broccoli in a hibiscus Commander Tso’s sauce or Roasted Potato Gnocchi with oxtail, kabocha squash, and truffle. Go overboard with not Tres but Cinco Leches Cake for dessert.

Stay: While the Blackwell Inn caters to more of a business crowd and the austere exterior may not spark much joy, you’ll love the 4-star accommodations and service that come with this surprisingly affordable reservation. Don’t sleep on this one (but do sleep in it).

Breakfast: If diners were made for college seniors instead of grandparent seniors, they would be a lot more like Blunch, where bright colors and street-art-style murals decorate the funky interior. Diner standards like omelets, pancakes, and sandwiches are freshly updated (soyrizo instead of chorizo in your breakfast burrito, or perhaps just an avocado toast with balsamic drizzle?) and complemented by a variety of boozy brunch cocktails at bizarrely low prices.


Columbus to Purcellville, Virginia

6 h 40 m
350 mi
Route: Today’s drive is the longest of the trip clocking in at just over 6.5 hours traveling west into northeast Virginia. If you want to shave a little time off, you can buy back a half-hour by skipping the roadside attraction below and taking a slightly more streamlined route.

Roadside Attraction: If six straight days of whiskey is turning you into something of a basketcase, you’ll want to stop for a photo with the World’s Largest Basket on Main Street in the little town of Dresden, Ohio. It’s 48 feet wide, 11 feet long, and 23 feet high, making it larger than some houses but nothing in comparison to the 7-story basket-shaped former headquarters of Longaberger 25 miles away in Newark, Ohio.

Eat: You’ll want to get to Purcellville early enough to explore so we don’t recommend stopping for long today, but you’ll need lunch. You’re welcome to stop at any service station along the route but if you prefer something a little quainter, pop into The Casselman in Grantsville, Maryland, 4 hours into your drive. You’ll find simple, country food with Pennsylvania Dutch and Amish influences, especially in the bakery downstairs, where there’s also an antique shop. (And, technically, this adds a stop in a 7th state to your journey, but who’s counting?)

Do: 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-induced activity, there aren’t many spots more charming than Blooming Hill Lavender Farm, open to the public for strolling and shopping.

Eat: Don’t be fooled by the fact this one appears to be inside a barn: Magnolia at the Mill is the best spot in town for a chic dinner on the more comfortable side of upscale. You’ll find filet mignon, seared salmon with lump crab, and shrimp and grits served on white linen cloths, but you’ll also be in luck if you’re looking for hickory grilled burgers or brick oven pizzas.

Stay: Springdale Village Inn is the bed and breakfast for you in Purcellville. Colonial-cottage-decorated rooms provide cozy accommodations in the federal-style estate house believed to be one of the last stops on the Underground Railroad, just 14 miles from the border to freedom. The five acres of bucolic bliss are well-worth wandering, too.

Breakfast: Sit down early to Springdale Village Inn’s daily farm-to-table breakfast and load up properly for the two-distillery day with a considerable drive between.


Purcellville to Maxwelton, West Virginia

5 h 20 m
320 mi
Route: Head a bit further east today before looping back westward toward your origin in Kentucky. You’ll make it just about halfway, stopping in West Virginia for a little more whiskey and a good night’s sleep.

Town: Alexandria, Virginia. Your first whiskey stop today may be a surprising one. 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. Washington’s recipe is once again being produced, in very limited batches, since the distillery’s reopening in 2007.

Town: 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. A tour before your tasting will take about 30 minutes.

Eat: Have lunch in Manassas before the final 3.5-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, mac-n-cheese, and baked potato on a menu that also includes specialty sandwiches like a brisket and pulled pork po’boy and a few juicy burgers. If you’re feeling the need to be somewhat healthy, try the Cajun Chopped Salad with brisket.

Do: 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. Smooth Ambler specializes in bourbon whiskies, so be sure to take some comparison sips before returning to limestone-laced Kentucky tomorrow…for research.

Eat: Most of the area action is in Lewisburg, 5 minutes from Maxwelton, and it’s here that you’ll find Food & Friends, a neighborhood favorite for a good meal and equally good atmosphere. Check out the char-grilled menu for brisket, pecan-crusted chicken, and baby back ribs, or try the bourbon-glazed salmon (also char-grilled).

Stay: Maxwelton/Lewisburg isn’t exactly a tourist area, so you won’t be staying in town. Luckily, there’s a sweet little apart-hotel in nearby White Sulphur Springs, about 15 minutes away, and you’ll spend a comfortable night here at Howard’s Creek Inn.

Breakfast: Back in Lewisburg, hit up The Wild Bean for a dependable breakfast of Huevos Rancheros or the Papas Platter of home fries, fajita veggies, and avocado topped with buttermilk crema and salsa. You can also try the scrambled eggs menu, with plenty of add-ins like black beans, jalapeños, spinach, or sautéed peppers and onions.


Maxwelton to Louisville, Kentucky

5 h 30 m
360 mi
Route: As easy as it gets, hop on I-64 W and take it back to Louisville.

Town: Charleston, West Virginia. Stop in West Virginia’s capital city about 3.5 hours into your drive to stretch your legs. Take a walk along the Kanawha River and check out Haddad Riverfront Park before strolling down Capitol Street in town. Make your way to Capitol Market on Smith Street to peruse the vibrant indoor-outdoor market and grab lunch before hitting the road again.

Eat: It’s been a fairly meat-forward trip, as you’d expect from this barbecue-loving region of the country, so step back from the pit for the afternoon and try some Cajun pasta with shrimp or good old fashioned spaghetti and meatballs in spicy puttanesca sauce at Soho’s Capitol Market.

Do: 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 hyper-modern outfit with an art collection as covetable as its spirits. 

Eat: 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. Potatoes are particularly prized here, too, with their own section on the menu.

Stay: The Louisville hotel scene is small but surprisingly strong. End your trip on a provocative note with a stay at Vu Guesthouse, a boutique with mystique to spare. Inside an old tobacco warehouse in the Smoketown neighborhood, the luxury boutique is equal parts sexy and gaudy, and whether or not it takes itself seriously is anyone’s guess but it’s comfortable, fun, and an unbeatable backdrop for some memorable last-night-of-the-trip photos.

Breakfast: For your final meal of the journey, head to Highland Morning for big portions of biscuits and gravy, crab cake benedict, or a bacon and fried egg sandwich on an English muffin. If you want to treat yourself, indulge in the sinful pancake menu, where Dreamsicle, Key West Key Lime, and Strawberry Shortcake are just a few of the tempting varieties available. Go big and go home.


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