Back in 1964, Congress declared bourbon “America’s Native Spirit,” and although it’s been around since before Prohibition, it’s never been as hot as it is right now. Evidence of the bourbon boom is everywhere: on television (inspired by shows like Mad Men), in the cocktails at super-hip craft bars, and even in gourmet cuisine. There’s perhaps no better place to explore the past, present, and future of bourbon than on Kentucky’s famed Bourbon Trail.
The delicious journey will take you through the big cities of Louisville and Lexington, as well as smaller spots like Bardstown and Loretto. Along the Kentucky Bourbon Trail, you’ll find both bourbon and a mix of the Bluegrass State’s urban-cool vibe, small town charm, and backroads beauty. A few notes though—many of the distilleries on the trail only offer tours at certain times of the day, and the distilleries are fairly spread out, so you’ll need to plan ahead if you want to get all nine stamps in your Kentucky Bourbon Trail passport (and a free t-shirt). Here’s how you can do it in just five days.
A Quick Note on Drinking and Driving: Don’t worry—we are not encouraging drunk driving by suggesting that you drive on the Bourbon Trail. All of the distilleries on the trail are legally limited by how much alcohol they can give you to sample (well under two ounces per person—total), and they cannot sell alcohol to consume on the premises either, so you will definitely not be leaving any stop even slightly buzzed. Once you’ve reached your town for the night, leave your car and walk or take a taxi if you plan on drinking more. I used the ridesharing app Lyft in Louisville and Lexington and had a designated driver at our ready in less than five minutes every time.
Day One
Land at the Louisville airport, and pick up your rental car. Unlike at many major airports, the rental car lot is a less than five-minute walk from the arrivals area, so there will be no painful waits for shuttle buses to slow you down here, and you can be on your way and drinking bourbon in no time.
Head straight into downtown Louisville for a 2 pm tour at the Evan Williams Bourbon Experience, the most modern and flashy stop on the trail. It feels like a bourbon theme park and is a fun way to shake off your flight, especially once you get to the tasting. The tour lasts about an hour, and then you’ll have the rest of the afternoon free to explore Louisville.
If you’re staying at the 21c Museum Hotel, grab one of the free guest bikes and pedal down to the gorgeous Louisville Waterfront. Then, get ready to check another state off of your bucket list map, because you’re headed to Indiana via the Big Four Bridge. The Big Four Bridge is a former railroad truss bridge that was recently converted into a pedestrian and bicycle bridge. It’s an easy half-mile ride across from Louisville to Jeffersonville, Indiana, and the panoramic Ohio River views and piped in classical music from the speakers overhead will make your crossing feel practically magical. After you’ve explored the parks on both sides, head back into Louisville for dinner at Bourbons Bistro. Located in a historic building that dates back to the 1870s, this restaurant is home to over 130 bourbons. Can’t make up your mind? Give the expert bartenders a price point and a sense of what you like to drink and let them create a custom bourbon flight for you. Since the flight sizes are smaller than a normal pour, you can try tipples you can’t afford to pay for by the glass for—like the Pappy Van Winkle 13-year. The food here gives the bourbon a run for its money, so if you’re not in a food coma after dinner, head down the street to catch a live bluegrass show at the Monkey Wrench.
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Stay: Ever slept in an art museum? The 21c Museum Hotel is not just a 91-room boutique lodge—it’s also a contemporary art museum. You can take one of the free guided museum tours or just wander around enjoying the pieces at your own pace. For a great view of downtown Louisville, try for one of the rooms with a rooftop terrace overlooking historic 7th Street.
Day Two
Use the morning to finish up in Louisville—maybe “swing” by the Louisville Slugger Museum if you’re into baseball, or head to the Muhammad Ali Center if boxing is more your style. On your way out, enjoy the 11 am Bulleit Frontier Whiskey Experience at Stitzel-Weller, where you’ll get to tour the grounds and taste bourbon. It’s a quick 21-mile drive from here to your next stop, the Jim Beam Distillery in Clermont.
Note that the Jim Beam tours are one of the longest on the trail, at an hour and 30 minutes. Jim Beam makes more than 50 percent of the bourbon in Kentucky, and its working distillery offers an in-depth look into bourbon-making. You’ll get to see every step of the process—and even lend a hand, helping to bottle the product (you can even buy the exact bottle you helped make, complete with your fingerprint in the wax seal, in the gift shop at the end of the tour).
After your tasting, enjoy lunch in a rocking chair on the porch of the distillery’s restaurant, Fred’s Smokehouse—do not leave without trying the bourbon ice cream! (Pro tip: For maximum tastebud joy, get the bourbon sauce for the bourbon bread pudding drizzled over your ice cream.)
To work off all of that bourbon ice cream, tackle the trails at the Bernheim Arboretum and Research Forest, which is just down the road (less than a five-minute drive) from Jim Beam. If you’re visiting on a weekday, the park is free (on weekends, there is a $5 per car environmental impact fee). You’ll find over 35 miles of (non-bourbon) trails here, which wind around a lake, through the forest, and down valleys. If you’re lucky enough to visit in the fall, the foliage is spectacular.
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Stay: Shepherdsville is a convenient layover between stops on the Bourbon Trail. The Best Western Plus South offers clean, quiet, and spacious rooms.
Day Three
This morning, you’re off to Maker’s Mark in Loretto, about an hour away from Shepherdsville. Maker’s Mark was designated a National Historic Landmark in 1980, and it’s the oldest operating bourbon distillery in the world. The bottling floor (and the tasting room) is a tour highlight—those iconic red wax bottles are hand-dipped!
Today is based around Bardstown, known as the “Bourbon Capital of the World” as it’s home to five distilleries (only three of which are on the official bourbon trail). There’s definitely more here than spirits though—it was recently selected as the “Most Beautiful Small Town in America” in the Rand McNally/USA Today Best of the Road contest and voted into the top 20 of “America’s Favorite Towns” by Travel + Leisure readers. Bardstown is also host to the Kentucky Bourbon Festival every September, which drew over 50,000 attendees in 2014.
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Get your introduction to the town by stopping for lunch at Kurtz’s Restaurant, a family-owned restaurant that has been serving up uniquely southern delicacies like pimento cheese, “hot brown”, congealed salad, and chess pie since 1937 (and has the epic family photos on the wall to prove it). If you want to try an authentic Kentucky dish, this is the place to do it.
Now that you’ve got a fully lined stomach, you can squeeze in a distillery that’s off the bourbon trail—Willett is just around the corner and offers tours on the hour 10 am to 4 pm Monday through Saturday (plus four tours on Sunday). Willett is a craft distillery, so it’s interesting to see the difference between a small-scale one like this and the larger ones you’ll see on the trail, like Heaven Hill Bourbon Heritage Center, which is your next stop (and just a few minutes away).
By now, you’ve seen plenty of rickhouses and fermenters, so the Whiskey Connoisseur Experience is your best option at Heaven Hill. You’ll get a short tour that focuses on the history of Heaven Hill, and then head straight into the tasting room for a tutored tasting of four premium/limited release bourbons. Cheers!
Back in Bardstown central, you can while away time wandering the cute streets, checking out the unique local shops, and admiring the scenery. When it’s dinnertime, Harrison Smith House is a perfect option. The outside patio is an intimate and relaxing spot to watch the town go by, or you can eat inside and enjoy the historical house’s interior. This is yet another spot in Kentucky with an impressive bourbon list, and the food here is a stand-out, especially for vegetarians (something I’ll admit I was not expecting in Kentucky).
For a nightcap, you can’t go wrong with a drink at the Kentucky Bourbon Marketplace. We tried the unique Jefferson’s Ocean Aged at Sea bourbon here, which may have traveled more than we have—this whisky ages while it journeys around the world, stopping at five different continents and crossing the equator four times, to absorb plenty of exotic flavor notes.
Day Four
Hope you’re ready for the breakfast of champions (bourbon and chocolate), because you’re catching a 10 am tour at Woodford Reserve this morning.
You’ll want to get up early and take your time on the drive, which winds past some of Kentucky’s most famous Thoroughbred horse farms—you might see the next Derby winner taking a break in a field. Woodford itself is one of the more scenic distilleries, thanks to its beautiful restored limestone buildings.
Your next few stops are all in the same place—you’re heading to the old James E. Pepper Distillery, which was recently transformed into a hip new restaurant and entertainment campus.
You’ll find lunch options here (and if you want to go the ice-cream-for-lunch route, Crank&Boom has you covered, with mouth-watering flavors like Honey Bourbon and Chocolate Stout). Be sure to swing by the Barrel House Distilling Company—a tiny operation that produces craft bourbon, moonshine, rum, and vodka—for a tour and tasting.
Right next door, Bourbon Barrel Aged Coffee finishes off its beans in used bourbon barrels, making a richly sweet flavored brew.
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When you’re done exploring the shops and restaurants here, hop on a late afternoon tour at Town Branch Distillery, which is just down the street. Owned by the larger Alltech corporation, you’ll find both beer and bourbon here. If you love both, the Kentucky Bourbon Barrel Ale or Stout (aged in bourbon barrels) will be right up your alley.
After checking into the Campbell House, take the hotel’s free shuttle into downtown Lexington—the pedestrian Short Street is a great place to start, and you can walk to plenty of bars and restaurants from here.
Stay: The Campbell House, an elegant hotel that’s been around since 1949 (but recently underwent a multi-million modernization). If you’re in town during a University of Kentucky game, you might even run across locals “tailgating” on the front porch here.
Day Five
Kentucky’s famous limestone water is known for making two things great—its bourbon and its horses. You’ve fully covered the spirits, so get up early and head out to Keeneland, one of the world’s most beautiful race tracks, to see some horses. The Thoroughbreds and their trainers run through morning workouts every day from about 6 am to 10 am, and anyone can come watch for free. The grandstands are deserted and you can get an up-close-and-personal view of future champions.
Wild Turkey is just 16 miles from Keeneland, so you can make it there in time for one of the first tours. The drive here is gorgeous, especially in the fall, when you take an S-shaped bridge that looks like something straight out of a car commercial. While on the tour, keep an eye out for the friendly distillery cat.
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Get that Bourbon Trail passport out—it’s time to get your last stamp at Four Roses Distillery, which looks quite different from your other stops, thanks to the Spanish Mission-style architecture built in 1910. Take time to smell the flowers that the distillery is named after—there are plenty on the grounds.
Take a victory lap to the Louisville Visitors Center, where you can show off your completed passport in exchange for a very special Kentucky Bourbon Trail “Finisher” t-shirt. Celebrate your accomplishment with drinks and dinner downtown, or by picking up an Urban Bourbon Trail map and starting a new challenge.
Stay: The Seelbach Hilton, one of F. Scott Fitzgerald’s favorite haunts. You may recognize the Seelbach as the venue for Tom and Daisy Buchanan’s wedding in The Great Gatsby.
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More from SmarterTravel:
- 10 Iconic Things You Can Only Do in America
- 10 Small Towns with Fantastic Fall Color
- 7 Sensational Scenic Drives for autumn
Caroline Morse traveled to Kentucky courtesy of Kentucky Tourism. Follow her adventures (bourbon-fueled and otherwise) @TravelWithCaroline and on Twitter @CarolineMorse1.
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