View Road Trip USA: Kentucky’s Bluegrass & Bourbon Trail in a larger map

Kentucky's legendary distilleries have crafted the world's finest bourbons for more than 200 years, using secret recipes and a time-honored process passed down from generation to generation. Following the Bourbon trail, you'll discover the art and science of the Master Distiller, savor the distinct flavor, and see how Kentucky's inherent mix of weather and pure limestone water produces that distinguished taste and deep amber color of America's Official Native Spirit. Winding along country roads, exploring historic towns, and listening to the sounds of the rolling green hills, Bluegrass Country will overwhelm you with its gentle, honest charm.

Fly In/Out: Lexington Blue Grass Airport

Day #1: Lexington

A peaceful road in Versailles, Kentucky (creative commons/code poet)

Arrive in Lexington

Arriving at a place called Blue Grass Airport should put you in the mood right away. Want to get even more relaxed? Start off your Bluegrass tour with a round of golf at one of Lexington's extremely affordable world-class golf courses. The city boasts eight courses in Lexington proper with two dozen more in the outskirts. If golf's not your thing, grab a Mint Julep and test your luck at the Keeneland Race Course. You'll soon see why they call Lexington the Horse Capital of the World.

Woodford Reserve Distillery (20 miles; 40 min)

Woodford Reserve is the oldest and smallest distillery in Kentucky, tracing its origins to 1797 when Elijah Pepper began distillation. This National Landmark boasts the only copper pot still and triple distillation process used to handcraft bourbon today. Woodford Reserve offers three different types of tours depending on what kind of experience you want to have.


Founded in 1792, historic Versailles is surrounded by serene farmland and some of the most famous horse farms in the Bluegrass Region. It also boasts some of Kentucky's best bed and breakfasts like the award-winning A Storybook Inn, with a perfect 5.0 score on TripAdvisor and a Best of the South ranking from Settle in and sober up for the long day of drinking ahead.

Day #2: The Bourbon Trail

A statue of Jim Beam is seen at the distillery in Clermont, Kentucky (REUTERS/Daniel Wallis)

Lawrenceburg (15 miles; 30 min)

Pace yourself, there is a long day of bourboning ahead! Lawrenceburg is home to two distinct distilleries, Four Roses and the ever-popular Wild Turkey. Four Roses calls its distillery tour a mellow experience where you can step back in time and enjoy the family practice of bourbon-making. Visiting the distillery of Wild Turkey, one of the best-selling premium Bourbons in the world, is a slightly grander experience. Make sure to grab lunch at one of the charming restaurants in historic Lawrenceburg before heading off to Loretto.

Loretto (55 miles; 1 hour)

The Maker's Mark distillery looks just like the bottle, with touches of the signature wax red color sprinkled about the perimeter. Cushioned by a bushy countryside that whispers serenity, this distillery bills itself as the friendliest, most welcoming in the area, offering an up-close and personal look at the whiskey process and the dream behind it.

Clermont (30 miles; 45 min)

Visit the home of the No. 1 selling bourbon in the world. That is, of course, the Jim Beam distillery. The tour wanders through the oldest rackhouse of Kentucky's signature bourbon and offers information on how generations of Beams have crafted whiskey since 1795. Best of all, the tour ends in the T. Jeremiah Beam Home, a National Historic Landmark where you can sample a selection of premium bourbons. Head to Louisville (25 miles; 30 min) before dark and walk off that bourbon buzz along the Ohio River.

Day #3: Louisville to Lexington

Early morning workouts at Churchill Downs in Louisville, Kentucky (REUTERS/John Sommers II)

Detox at Jack Fry's

Grab a gentlemen's lunch at Jack Fry's, the 17-time Best of Louisville award-winning restaurant. Jack Fry's was established in 1933 by, you guessed it, Jack Fry, who was known as a rambling, gambling kind of guy who loved amateur boxing and the ponies. As a result, Jack Fry's became a sportsman's hangout and he was said to conduct his bookmaking and bootlegging affairs from the back room. Today, the spot retains its rough-and-tumble persona, but bolsters it with a menu of Louisville's finest cuisine.

Louisville to Lexington (75 miles; 1 hour, 30 min)

Louisville is best known as the home of the Kentucky Derby, an event that's drawn aristocrats to Churchill Downs since 1975. But there's more to this city than horse racing. Louisville has a vibrant waterfront, modern museums, lively blue-collar neighborhoods, and the largest collection of Victorian homes in the country just south of downtown in Old Louisville. After sufficient exploration, shoot across I-64 back into the rolling pastures of Bluegrass Country on the short jaunt back to Lexington.


Cap off your tour through Bluegrass Country with its namesake music. The distinctive American form popularized by Kentuckian Bill Monroe and his group the Bluegrass Boys in the 1940s can be found across Lexington. Your bests best are Southland Jamboree, Cosmic Charlie's and Al's Bar. In the summer months, look out for Red Barn Radio shows at ArtsPlace or concerts at Collins Bowling Alley.


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