Rolling hills dotted with centuries-old trees, split rail fences corralling thoroughbred racehorses, and the world’s finest bourbon are what most people envision at the mere mention of Kentucky. Because it’s all true, especially in and around Bardstown — the commonwealth’s second oldest city, located at the head of the bourbon trail and just 37 miles outside of Louisville. Of course, you don’t have to be a bourbon aficionado to visit Bardstown, but it certainly doesn’t hurt. In town, tour storied distilleries in the place where bourbon was born; eat a Kentucky hot brown in a circa-1779 tavern; tour one of the nation’s best Civil War museums; and more.
Activities: Get your Kentucky Bourbon Trail passport started off with a cluster of stamps with tours of celebrated bourbon distilleries such as Maker’s Mark, Jim Beam, Barton 1792, Four Roses, and Heaven Hill. Take a self-guided walking tour of historic downtown Bardstown — maps are available at the welcome center — and shop at local boutiques and art galleries. Or enjoy a scenic 37-mile round trip train ride on My Old Kentucky Dinner Train, which offers elegant lunch and dinner excursions as well as murder mysteries in 1940s-era vintage train cars. It’s a splurge at $70-$111, but a ride is also one of the best ways to see the area’s lush landscapes.
Eating: At the circa-1779 Old Talbott Tavern, get loads of history along with signature Kentucky dishes — such as Southern fried chicken, stew-like Kentucky Burgoo, and a Kentucky hot brown (an open-faced sandwich containing smoked turkey and sugar cured ham, smothered with béchamel sauce and melted cheddar, and topped with bacon and tomato). A hidden gem — literally, as it’s hard to find — is the Rickhouse Restaurant & Lounge, named after the warehouses where bourbon is left to age in barrels. The establishment is known for its steak, but it also offers pasta, poultry, and, as you might imagine, an extensive bourbon list (in addition to a hearty wine and beer selection).
Drinking: The Kentucky Bourbon House, located in the historic circa-1787 Chapeze Mansion, offers tastings, mixology classes, and more than 90 premium Kentucky bourbons. For those seeking a bourbon break, the area has several wineries offering tours and tastings, and you can knock back craft brews at the 3rd Street Taphouse.
Museums: The Civil War Museum ($10) is the largest and most complete Civil War museum in the United States. The impressive collection is housed in a more than 8,000-square-foot space and contains both Union and Confederate displays. It’s located in Museum Row, which is also home to the Women’s Museum of the Civil War, the War Memorial of Mid America, and Old Bardstown Village — comprised of 10 log structures dating from the 18th and 19th centuries.
Love to see how people lived in times gone by? My Old Kentucky Home State Park ($5-$10) is home to the historic Federal Hill Mansion that inspired Stephen Foster to write the now-famous song “My Own Kentucky Home.” Built between 1795 and 1818, the Georgian-style brick mansion was home to the original family for three generations before being sold to the Commonwealth of Kentucky. You’ll find a large collection of family heirlooms within, including some of the top examples of American furniture.
Stay: Follow in the footsteps of President Abraham Lincoln, Jesse James, Daniel Boone and Washington Irving, to name a few, and stay at the aforementioned Old Talbott Tavern. Continuously operated since the late 1700s, the tavern offers food, lodging, and, of course, libations — it’s the world’s oldest bourbon bar. The staff is happy to point out bullet holes in a couple of paintings, said to be shot up by none other than the outlaw Jesse James during his stay. There are six rooms, $76-$120 per night, each named after a famous patron. We’re partial to the Lincoln Suite, which has a sitting room, a full size antique Lincoln bed (naturally), and an antique claw foot bathtub with shower.
Getting There: Fly into the Louisville International Airport and drive 41 minutes to Bardstown; or land at the Blue Grass Airport in Lexington, Kentucky and drive one hour.