Lexington, Kentucky is located about an hour from the bigger city of Louisville, right in the heart of horse and bourbon country. Most of Lexington’s best activities involve these two pleasures in some way, whether it’s catching a race day at Keeneland Race Course, touring a horse farm, or exploring the many fine distilleries of the Kentucky Bourbon Trail.
A mid-size, manageable city surrounded by the rolling, bluegrass hills of Kentucky lore, visitors will split time between the city of Lexington itself, where a burgeoning dining scene fills the historic downtown streets, and in the neighboring countryside that’s home to thoroughbred farms, bourbon distilleries, and off-the-beaten-path dining options.
America’s top bourbon distilleries can be found around Lexington, where the water is sweet and history of the craft runs deep. Distillery tours come with bourbon tastings, views of the Kentucky countryside (and historic architecture), and engaging lessons on the distillery process and its history. Some distilleries, like Woodford Reserve (a crowd favorite), also serve lunch. There are many sites to choose from, with popular standards like Maker’s Mark and Four Roses, and other newer, small distilleries in beautiful historic settings.
The Kentucky Bourbon Trail website, an interactive map of distilleries, nearby restaurants, and farms (and tips for tours and travel arrangements), helps make bourbon an entire tourism industry in of itself.
There are a few transportation options for visiting distilleries, and booking a tour, biking, or using a rideshare app are all fine choices. If you decide to tour on your own, don’t forget a designated driver.
Place Your Bets at Keeneland Race Course
Keeneland Race Course is horse country’s premier thoroughbred auction house, and one of the most enjoyable (and classy) places to catch a race anywhere in the country. Thoroughbreds at Keeneland race during the fall and spring (October and April), but you can tour the facilities year-round, or attend one of Keeneland’s many seasonal events. Race days are for much more than betting, with great dining, shopping, and cocktail-sipping options on the grounds as well. Sunrise Trackside is a Saturday morning event catered to families and early risers, where guests can watch trainings, take tours, and enjoy a trackside breakfast.
Keeneland is located across the street from Lexington’s Blue Grass Airport, and about a 10-minute drive from downtown. Race day tickets are $5 to $10 for general admission and grandstand seating, and $55 to $110 for dining buffet and interior viewing options, ranging from casual to luxe.
Have an Adventure at Shaker Village
A scenic step back in time, seldom experienced elsewhere, The Shaker Village at Pleasant Hill is dedicated to the Kentucky Shaker community, preserving their unique way of life. Beautiful, historic buildings and surrounding farm country offer many possibilities for the whole family: farm tours, nature walks, river cruises, and horseback rides just name a few. Dine on dishes created from the village’s garden, at their farm-to-table restaurant, and even stay in a chic, farmhouse-inspired guest room at one of the property’s landmark buildings.
The Shaker village is located in Shakertown, about a 30-minute drive from downtown Lexington.
Visit the Kentucky Horse Park
Kentucky Horse Park is a fun, all-inclusive way to get excited about horse country and familiarize yourself with the basics. Guided horse and pony rides ($5 to $25), several museums and galleries (including the International Museum of the Horse), barn tours, and memorials of former champions are all included. The big events here are the park’s hosted equestrian shows, opportunities to see some of the finest horses and athletes in the world in trail competitions, jumping, steeplechase, and other heart-racing events.
Kentucky Horse Park is located off of I-75, about 15 to 20 minutes from downtown Lexington. Admission costs are $20 for adults, and $10 for children six and older (children under six are free).
Go to a Horse Farm
Exploring a horse farm in Lexington provides behind-the-scenes context to the races, the animals, and the region, as well as gorgeous, sweeping views of bluegrass country—and some quality time with these beloved animals. Tours at Mill Ridge Farm, a family-run facility, home to many past (and future) racing champions, include expert information on the ins and outs of the business, and the horses and people who made it happen over the years.
There are more than 400 horse farms in the region, but several guided tour options (combining transportation, lunch, and visits to a few farms—and occasionally a distillery or two) make visiting the farms convenient and fun.
Delve Into the Boozy History of the Distillery District
A short trip from downtown, and minutes from McConnell Springs (home to Lexington’s first settlement), is the Distillery District, a recently revitalized historical area brimming with new businesses and entertainment. Buildings here were all once part of the James E. Pepper Distillery, one of Kentucky’s oldest bourbon makers, which first started during the American Revolution. After decades of ups and downs in the whiskey business and otherwise, James E. Pepper reopened as a smaller, craft distillery with much historical significance—all told through a guided tour of the facilities. A $20 tour comes with multiple tastings and a complimentary whiskey glass.
Listen to Live Music
Bluegrass is certainly Kentucky’s most popular (and historic) genre of music, and there are several festivals dedicated to talented fiddlers throughout the year. Festival of the Bluegrass, in June, is the region’s oldest bluegrass festival, still going strong, and Southland Jamboree’s ongoing bluegrass concert series is a fun (free) way to catch live, outdoor music. In August, Railbird Festival at Keeneland Race Course combines the best songsters in Appalachia with the region’s other great exports: bourbon and horses.
Regular Bluegrass and Americana live sets are held at The Burl, and other small venues throughout downtown Lexington.
Sample the Best of Lexington at These Restaurants
Lexington restaurant menus vary from trendy recipes and the newest haute cuisine, to the traditional, down-home Kentucky favorites that still inspire young chefs. Local chef Ouita Michel’s restaurants are a mix of the innovative and familiar: from Wallace Station, a casual stop for a “Hot Brown” (Kentucky’s signature turkey melt) in between distillery tours, to her chic-yet-homey farm-to-table restaurant Holly Hill Inn—great for a weekend Bluegrass Brunch. Barbecue is an essential meal while in Lexington (County Club can’t be beat), as is one fancy, old-school night out at Dudley’s on Short.
Tour Lexington’s Historic Houses
On West Main Street in Lexington, one can visit the childhood home of esteemed former first lady Mary Todd Lincoln. The historic house is now a museum with a collection of art and period pieces, and detailed information on the history of the Todd and Lincoln families. The tour costs $15 for adults.
Other historic houses of note in the neighborhood are Henry Clay’s impressive Ashland Estate, and the antebellum mansion of Waveland. Both estates offer guided tours of the historic grounds, providing glimpses into a bygone way of life.
Visit the Largest Abe Lincoln Mural in the World
It’s worth taking a detour through downtown to see this whopping 60-foot mural of Kentucky-born Abraham Lincoln, the world’s largest mural of the president. Brazilian artist Eduard Cobra completed the mural in 2013, combining this classic image of Abe with more contemporary (and colorful) artistic expression. The mural is located on the back wall of the Kentucky Theatre on East Main Street in downtown Lexington.
Sip the Night Away at Lexington’s Best Cocktail Bars
Lexington’s hip cocktail scene only continues to grow, as craft mixologists jump at the chance to use locally-made spirits. After sampling bourbon at its source, on a distillery tour, Lexington visitors can try it in a few other iterations (whether in a classic mint julep or a brand new creation). At hip, modern cocktail bars like West Main Crafting Co and Ona, ambitions go way beyond bourbon, with full menus of interesting infused and barrel-aged spirits in combination with other housemade ingredients. On the classic side of things, there’s The Bluegrass Tavern, boasting the largest collection of bourbon in the state with more than 150 different bottles.
Shop and Dine at Fritz Farm
The Summit at Fritz Farm combines the beauty and leisure of a public park with the convenience and commerce of an outdoor mall. Here is Lexington’s first premier food hall, a great place to sample Lexington’s best (and latest) flavors, and a shopping center full of local boutiques and favorite higher-end chains. A calendar of activities varies by season: At night, during the summer, there are free concerts on the green, moonlight movie showings, and weekly farmer’s markets.
Fritz Farm is located off of US-27, about a 20-minute drive from downtown Lexington.
Explore Downtown Lexington
Downtown Lexington is a good mix of the young and old, and of both small town and big city vibes. Its architecture spans about 200 years, and there are historic walking tours through the various stages and major players of the city. Strolling through on your own, there are breweries, cafes, restaurants, historic green spaces like Thoroughbred Park, and small museums, theaters, and shops. An arts and culture-forward city, even downtown Lexington accommodations, like the 21c Museum Hotel, are full of fine contemporary paintings and sculptures.