8 Can’t-Miss Things to Do in Kentucky Derby Country

Sample “America’s native spirit” in distilleries along the Bourbon Trail. There are now dozens to choose from, and distillers have upped the ante by offering a variety of tours,  expanding visitor centers, and gift shops—some even offer food trucks and live music. Castle & Key, in Frankfort, is located on a historic distilling site dating back to 1887. After a tour of the grounds (watching the barrels being rolled into the barrel house is quite the sight), settle in for a bourbon tasting that also includes their own vodka and gin. A few other top-notch distilleries to plan tours and tastings include Jim Beam in Clermont, Woodford Reserve in Versailles, and Maker’s Mark in Loretto.

Some distilleries now offer full-service restaurants, including Jim Beam’s Kitchen Table, a homey spot with wood accents and an outdoor patio. Sip expertly made bourbon cocktails and sample down-home dishes with a twist, like fried catfish served with black-eyed peas and a harissa aioli. In Lexington, acclaimed chef Ouita Michel’s hotspot Honeywood features a selection of shared plates (cornmeal fried oysters, deviled eggs) along with tasty mains like a smoked pork chop with butter beans and green tomato jam. A good spot for lunch is Greyline Station, a recently opened marketplace/food hall in a former bus garage with vendors offering everything from taco salads at The Social Vegan to freshly baked donuts at North Lime Coffee & Donuts. Dudley’s on Short and Lockbox are perennial favorites in the heart of downtown.

Over in Louisville, there’s Rosettes, helmed by James Beard Award-nominated chef Ashleigh Shanti, a rising culinary star who specializes in Appalachian soul food (standouts include oxtail and roasted chicken). Start with a handcrafted cocktail (perhaps the tequila-based Alberta’s Law) in the charming bar room overlooking the Ohio River. The House of Marigold is a fun new daytime spot with locally sourced salads and brunch items, while Proof on Main and Jack Fry’s are local mainstays.

You can’t leave town without digging into a Hot Brown, the famous open-faced roast turkey sandwich topped with bacon and tomatoes and smothered in a cheese sauce, which was created at the Brown Hotel. Built in 1923 (it’s celebrating its 100th anniversary with special programs throughout the year), this Georgian-Revival institution still marvels visitors with its architectural details, including ornately painted ceilings with gold inlay, elegant chandeliers, and marble columns. And there’s no better place to sip a single barrel bourbon than the Lobby Bar.

The state’s two most famous tracks for thoroughbred racing, Churchill Downs (Louisville) and Keeneland (Lexington), are open year-round, though racing meets only take place in spring and fall. Keeneland, built in 1936, is a National Historic Landmark and is especially beloved by locals. On a tour, you’ll see the track and other spots used in several horse racing films, including Seabiscuit and Secretariat.

Of course, Churchill Downs is home to the Kentucky Derby. The world-famous track with its notable twin spires dates back to 1875. It’s definitely worth a tour so you can learn about the history (a few years prior, Colonel Meriwether Lewis Clark attended the Epsom Derby in England, which fueled the idea to create a similar racing spectacle in America), see the paddock and the grandstand and the exhibits in the Kentucky Derby Museum. Tours are booked through the museum, which recently added a permanent exhibit on the 50th anniversary of Secretariat’s historic Triple Crown sweep in 1973.

A new crop of boutique hotels is creating quite a buzz around town. In Louisville’s hopping NuLu neighborhood (short for “New Louisville”) is the 122-room Hotel Genevieve featuring a pair of bars, a speakeasy-style hideaway, and a rooftop lounge. Opening by summer’s end in the hip Highlands area is the 65-room Myriad Hotel with a sultry poolside scene centered around cabanas and a fire pit (its sister property is the revamped mid-century Bardstown Motor Lodge in the heart of Bourbon Country).

Another boutique hotel has opened in Lexington’s Distillery District, a 25-acre entertainment complex on the site of the former James E. Pepper Distillery. The Manchester is a handsome retro-chic hotel with 125 rooms done up with exposed dark wood and leather accents. Lost Palm, the tropical-themed rooftop lounge, is a fun spot for drinks and snacks, while the ground-floor restaurant serves modern Appalachian-inspired fare such as braised boar and confit rabbit ravioli by executive chefs and husband-and-wife team Karl and Paula Lowe.

Many may not know that Muhammad Ali, born Cassius Clay in 1942, is a Louisville native. At the engrossing Muhammad Ali Center, learn about the legend’s storied boxing career and his many humanitarian efforts, both highlighted with historical footage and artifacts. Also worth a visit for baseball fans is the Louisville Slugger Museum & Factory, where the famed wooden baseball bats still used by major leaguers are manufactured (its 120-foot-tall bat outside the building is tailor-made for selfies). If you’re interested in seeing the artwork, you can head to Lexington’s University of Kentucky Art Museum, which offers rotating exhibits (always free), including an upcoming exhibition on American modernist Edward Fisk (Aug. 1, 2023–Jan. 13, 2024).

The Kentucky Derby is said to be the oldest continuously running sporting event in the country (like the track, it too started in 1875). While the race itself is known as “The Most Exciting Two Minutes in Sports,”—it’s an all-day affair with more than a dozen other races, wagering, eating and drinking in various venues and concessions, and strolling the expansive grounds to see a one-of-a-kind fashion parade (some say the people watching rivals the horse racing).

Newly introduced in 2023 is the First Turn Dining Club and First Turn Reserved Seating, a $90 million indoor/outdoor complex up by the first turn of the track. It has space for 7,100 spectators (5,100 in grandstand-style padded seating and 2,000 in a 50,000-square-foot luxury club with reserved tables, unlimited food/drink, private wagering stations, and a large terrace directly on the rail for hard-to-beat views). Next year—the 150^th Run for the Roses—track enhancements are expected to include an expanded paddock and additional club seating options with reserved track viewing areas. If the Derby has always been on your wishlist, then heed the call of the bugle—but be sure to plan ahead as tickets, hotels, and packages sell out quickly!