A Lexington getaway doesn’t have to wait for the weekend. Whether you’re extending your stay or arriving early in the week, you’ll find plenty of ways to explore the city. From fascinating museums to thrilling outdoor adventures, you'll love these weekday wonders.
Musical Mondays
Pictured: Tee Dee's Lounge
Start your week with live music in Lexington, where bars, breweries, and clubs feature performances throughout the city. Catch a rotating lineup of local and touring acts at spots like Al’s Bar, The Burl, Manchester Music Hall, and Green Lantern, or check event calendars for special performances at venues including the Lexington Opera House, Central Bank Center, , and Lyric Theatre.
On Mondays, experience Lexington’s rich musical traditions at Old North Bar’s Old Time Jam, where musicians and friends gather for bluegrass, Celtic, Cajun, and other old-time sounds. Bring your instrument and join in, or simply enjoy the welcoming atmosphere.
At Tee Dee’s Lounge, catch living blues legend Tee Dee Young performing every Monday night at his namesake club. Doors open at 6 p.m., with music beginning at 8 p.m. The club regularly attracts talented musicians from across the country, making each performance a unique experience.
For a one-of-a-kind music experience, attend a live taping of Woodsongs Old-Time Radio Hour at the Scottish Rite Concert Hall. Recorded before a live audience almost every Monday, the program is broadcast via radio, web, and television to audiences around the world.
Experience Bourbonland
Pictured: Lexington Brewing & Distilling Co.
Bourbon has its roots in Kentucky, and Lexington is within easy driving distance of every distillery on the Kentucky Bourbon Trail, while offering unique bourbon experiences of its own. Make the most of your bourbon adventure with the Bourbonland Tasting Pass, which connects visitors with Lexington-area distilleries and offers exclusive perks along the way.
Visit Lexington Brewing & Distilling Co. to sample award-winning beer and spirits at one of the few joint brewing and distilling operations in the world. In the Distillery District, Barrel House Distilling Co. offers tours, tastings, and a gift shop stocked with house-made spirits, including RockCastle Bourbon and Devil John Moonshine. While you're there, enjoy local fare and craft cocktails at The Elkhorn Tavern next door.
Just steps away, the James E. Pepper Distillery crafts a variety of rye and bourbon whiskeys on the grounds of the original Pepper distillery, which opened in 1879. Tour the historic campus to learn about the Pepper legacy, sample award-winning bourbon, and browse the gift shop featuring locally made products. In Lexington's newest entertainment district, The Commons, RD1 Spirits celebrates the city's bourbon heritage while producing small-batch bourbon through modern techniques. Go beyond a traditional distillery tour with RD1's interactive thieving experience, where guests can sample bourbon directly from the barrel and learn more about the art of aging and blending whiskey. We recommend booking tours in advance or calling ahead for same-day availability.
Just a short drive from Lexington, Woodford Reserve and Bluegrass Distillers offer picturesque distillery experiences rooted in Kentucky bourbon history. At Woodford Reserve, tour one of the state’s oldest and most celebrated distilleries, explore the scenic grounds, and enjoy tastings featuring its signature bourbon and spirits. In Midway, Bluegrass Distillers produces small-batch bourbon, rye, and other spirits, offering visitors a look at the craft behind its locally made lineup.
Explore Horse Country
Pictured: Keeneland
No visit to Lexington, the Horse Capital of the World, is complete without a trip to a working horse farm. With more than 450 horse farms throughout the region, many of which offer their own unique tours, Visit Horse Country makes it easy to get an up-close look at Kentucky's Thoroughbred farms, medical facilities, and feed mills through personalized group, public, and private tours and experiences.
Step behind the scenes of Thoroughbred racing with a tour of the iconic Keeneland racecourse, or visit the Keeneland Library to explore one of the world's largest collections dedicated to the history of the industry. Start your day with the Morning Works Tour or a walk of the picturesque grounds, then grab breakfast at the Keeneland Track Kitchen before browsing the Keeneland Shop. Catch thrilling racing action during the spring and fall meets during April and October, or explore the grounds all year long.
For a full day of equine experiences, visit the Kentucky Horse Park to meet more than 30 breeds of horses, watch daily horse demonstrations, and explore the International Museum of the Horse and American Saddlebred Museum. The park offers a glimpse into Kentucky’s rich equestrian history, from the traditions of the equine industry to the legacy of the American Saddlebred. The Kentucky Horse Park is open Wednesday through Sunday and closed on Tuesdays, so plan your visit accordingly.
Located nearby in Georgetown, Old Friends Farm offers a unique opportunity to meet retired Thoroughbred racehorses and learn their stories. The nonprofit retirement farm provides guided tours where visitors can get an up-close look at some of racing’s most recognizable horses while learning about their lives after the track.
Outdoor Adventures
Pictured: Jacobson Park
From peaceful gardens and scenic trails to breathtaking views and outdoor adventure, Lexington offers plenty of ways to enjoy the Bluegrass at your own pace.
Start in the heart of downtown at Gatton Park, a vibrant gathering space where nature, public art, and community come together. While you're there, stop by the larger-than-life statue of Big Lex for a memorable photo. Discover where Lexington got its name at McConnell Springs, a 26-acre nature sanctuary featuring tranquil walking trails, natural springs, and an education center that brings the city's history to life. In the historic East End neighborhood, visit the Isaac Murphy Memorial Art Garden, the first park in the country dedicated to honoring the history and legacy of African American jockeys. Stroll through the garden's public art installations, learn about legendary horsemen including Isaac Murphy and James "Soup" Perkins, or set out on the Legacy Trail, a 12-mile path connecting downtown Lexington to the Kentucky Horse Park.
For hiking and exceptional views, head to Raven Run Nature Sanctuary, where more than 700 acres and 10-plus miles of hiking trails lead to scenic overlooks of the Kentucky River. If you're looking for adventure, Boone Creek Outdoors offers an unforgettable treetop experience with ziplines, sky bridges, and a floating staircase overlooking the beautiful Kentucky River Palisades. Get on the water at Jacobson Park or Kelley's Landing, Lexington’s first and only public access point to the Kentucky River, where you can rent kayaks, canoes, and paddleboats for a relaxing afternoon outdoors.
Discover Lexington's History
Pictured: Mary Todd Lincoln House
Discover Lexington’s rich history and cultural heritage through historic estates, museums, and one-of-a-kind attractions that bring the stories of the Bluegrass to life.
Take a walk through history as you explore the family home of one of America's most fascinating first ladies at the Mary Todd Lincoln House, where tours are offered Monday through Saturday from March through November. Ashland, The Henry Clay Estate, was once home to one of Kentucky's most notable statesmen. Tour the grounds, mansion, and exhibits Tuesday through Saturday.
Lexington's downtown public library branch is home to the world's largest ceiling clock, along with an art gallery featuring curated exhibits often highlighting local artists. Part of the UK College of Fine Arts, the University of Kentucky Art Museum is a free cultural destination open to both the campus community and the public. View nearly 5,000 objects from its permanent collection and rotating exhibits Tuesday through Saturday.
Explore even more of Lexington’s history at your own pace with the Historic Lexington Walk, which takes you through downtown to discover 33 points of interest along the way. With plenty of opportunities to stop for a meal, coffee, or a break, it’s an easy way to experience the city’s historic architecture and stories. For a scenic drive beyond downtown, follow the Bluegrass Country Driving Tour and discover rolling countryside, iconic horse farms, and some of Central Kentucky’s most picturesque landscapes.
In Winchester, go behind the scenes at the Ale-8-One Factory to see how Kentucky's Official Soft Drink is made, with Tuesday and Thursday tours available by online reservation.
Places to Play
Pictured: The Burl
Lexington is home to a variety of entertainment venues offering something for every type of outing. From axe throwing and pickleball to live music, movies, karaoke, and arcade games, there are plenty of ways to enjoy a night out throughout the city.
In The Commons, Battle Axes and Pickleball Kingdom offer opportunities for friendly competition. Battle Axes is a family entertainment center featuring axe throwing, high-speed go-karts, racing ziplines, cornhole, giant inflatables, a kids' area, and a rage room. Pickleball Kingdom offers 17 pro-grade indoor courts, free lessons, open play for all skill levels, and programming including tournaments and leagues.
Nearby in the Distillery District, The Burl Arcade combines classic arcade cabinets and pinball with craft beer, cocktails, and live music later in the week. Continue the fun at LexLive with bowling, arcade games, virtual reality, a movie theater, and plenty of screens to watch your favorite sports teams. For a more social night out, hop aboard the Pedal Pub for a unique way to explore downtown or visit PKL LEX for indoor pickleball, games, and social events. Round out your evening with a film, live performance, or special event at the historic Kentucky Theatre in the heart of downtown.
