Pappy, Ponies, and Underground Adventures: 4-Day Weekend in Louisville, Kentucky

race horse; Louisville
olgaru79 / Shutterstock

When you think of Louisville, three things should immediately come to mind: baseball, horses and, of course, bourbon. The big tourist draws to the largest city in Kentucky are worthy: The Louisville Slugger Factory and Museum; Churchill Downs, home of the Kentucky Derby; and the nearby bourbon trail, where you can visit the likes of Maker’s Mark, Heaven Hill, and Four Roses. But Louisville offers so much more with world-class museums, a rising local dining and drinking scene, and plenty of outdoor—and underground—sporting activities.

Tony Hale on His Go-To Oyster Bar and Why He Loves Birmingham

Read article


If you’re into art, you’ll want to book at the boutique 21c Museum Hotel, a hip 91-room art installation. Art abounds at this downtown spot, where rooms feature Malin + Goetz products and room service from acclaimed restaurant Proof on Main, located in the hotel. If you want a classic spot, you won’t go wrong with either the Seelbach, where F. Scott Fitzgerald often stayed and gained inspiration to write The Great Gatsby, or the historic and opulent Brown Hotel where you can not only sleep in a mahogany pillow-top bed with plush bedding, but you can indulge in the famous Hot Brown, an open-faced turkey sandwich with bacon and Mornay sauce.

Chocolate chip cookie preparation at Please & Thank You
Chocolate chip cookie preparation at Please & Thank You Courtesy Image


Start your day with a quick coffee, chive biscuit, and local eggs from Please & Thank You. Or sit down for a more proper breakfast or lunch at Blue Dog Bakery & Café (we suggest the poached egg and bacon pizza). Later, don’t miss the classic Louisville spot, Jack Fry’s. Opened in 1933, this French-influenced, Southern-focused fine dining spot is perfect for lunch or dinner (except during Derby weekend when it’s packed). No matter what you get—roasted new potatoes, asparagus, roasted garlic purée; za’atar-spiced and pan-seared scallops; or bourbon and peach–glazed chicken breast—you’ll leave happy. Lilly’s Bistro is where James Beard–nominated chef/owner Kathy Cary, a forerunner of Louisville’s farm-to-table movement, sources most of her ingredients from farmers around Louisville for her very locavore American menu.

For another well-credential chef, head to Edward Lee’s prix-fixe spot 610 Magnolia or his more casual Milkweed, where he and chef Kevin Ashworth blend Southern and Asian flavors in dishes like an organic pork burger with kimchi, or smoked soy shoyu veggie ramen. For a more casual meal, try out Garage Bar, set in a former auto shop in NuLu, focuses on seasonal, local-ingredient-topped brick oven pizzas, craft beers and, of course, bourbon.

The Best Boozy Advent Calendars to Kick Off the Holidays

Read article


Kentucky is bourbon country (its history dates back to 1774), and if you’re reading this, you’re likely already planning your bourbon stops. Start at the Urban Bourbon Trail, where you can visit the five founding bars—Bar at Blu, Bourbons Bistro, Brown Hotel Lobby Bar, the Old Sellback Bar, and Proof on Main. Dozens of additional bars and restaurants have joined on for the urban trail since its inception in 2008, so there’s no shortage of places to go. Two to check out: First, Silver Dollar has a 200-strong bourbon list (including a smattering of rye whiskey), all of which are available in tasting pours, and you can eat cornmeal-breaded fried oysters and spice-crusted baby back ribs while sipping your brown booze. Second, Haymarket, which opened in 2012, has 150 bourbons, including rare and private barrel selections, a 225-person music hall, and a packaged goods shop where you can buy bourbon, to go, late night. No visit to Louisville would be complete without a jaunt along the Kentucky Bourbon Trail. Hire a driver to take you out to Bardstown and the surrounding area to visit nine classic Kentucky distilleries, including Woodford Reserve, Wild Turkey, and Buffalo Trace, where they make Blanton’s, Eagle Rare, and Pappy Van Winkle.

The Louisville Slugger Museum & Factory
Joe Hendrickson / Shutterstock


Whether you want to get out and be active, stimulate your mind, or get schooled in the ways of bourbon, Louisville has plenty to offer. Start off at the Louisville Slugger Museum and Factory, where you can take in a 30-minute guided tour, watch bats get made, and then get your own personalized slugger. Next, pop over to the Muhammad Ali Center and learn all about the life of The Greatest. Last, head to Churchill Downs to knock around at the Kentucky Derby Museum and learn about the history of the Derby (dating back to 1875).

Now that you have your fill of local sports culture, it’s time to get active. Louisville has 122 urban parks, covering 13,000 acres. You can mountain bike on the 4-mile Otter Creek Trail in nearby Brandenburg or go inside to the Louisville Mega Cavern, the largest man-made cavern, with 17 miles of corridors for zip lining, aerial ropes, and the Mega Underground Bike Park, with 45 trails of single track, dual slalom, and jumps spread out over 320,000 square feet in a limestone cavern 100 feet below ground.

Insider Tip

Although you might be tempted, you should avoid 4th Street Live!—it’s a 350,000-square-foot tourist trap with chain restaurants and dueling piano bars (although the Jim Beam distillery is there).

For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!