Lexington, Kentucky, the vibrant heart of the Bluegrass region, is a captivating city nestled amidst a landscape of gently rolling hills and verdant horse farms. As your plane descends towards Blue Grass Airport, the panorama unfolding beneath you immediately reveals why Lexington has earned the moniker "Horse Capital of the World." A mesmerizing tapestry of over 450 horse farms stretches as far as the eye can see, painting the countryside in shades of emerald and jade. This is a realm where magnificent, multi-million dollar racehorses are revered as celebrities, their names sometimes even gracing the streets of the city.
However, to confine Lexington to merely horses and bourbon would be a disservice. Kentucky’s second-largest city is a treasure trove of art, history, and culture. Its strategic location makes it an ideal springboard for exploring some of the most breathtaking hiking and climbing destinations in the Southeast. A mere 48 hours in Lexington will only provide a tantalizing glimpse of the local culture that captivates so many visitors. Prepare to be charmed and start planning your return trip before you even leave!
Day 1: Morning
Begin your Bluegrass adventure with a stay at the 21c Museum Hotel Lexington, an establishment that is as much an art experience as it is a place to rest your head. Situated directly on Main Street, this eclectic, award-winning, 4-star hotel places you in the heart of downtown, within easy walking distance of enticing culinary experiences and the city’s vibrant nightlife.
10 a.m.: Immerse yourself in the equine allure of the Bluegrass region by encountering some of the majestic thoroughbreds that are so deeply celebrated here. Embark on a tour with Old Friends, a thoroughbred retirement and rescue farm located a scenic 20-minute drive north of Lexington (consider taking US-25 for a more picturesque route). These 90-minute tours are not only memorable and informative but also support a worthy cause. Alternatively, you can visit the nearby Kentucky Horse Park, another exceptional option. Time your visit to witness the captivating daily Parade of Breeds show, which commences at 11 a.m.
12 p.m.: For lunch, consider venturing further afield to Wallace Station, a renowned eatery situated along the famed Bourbon Trail, offering delightful outdoor seating. To return to town, take the scenic KY-1681 (Old Frankfort Pike), a road that winds through the heart of horse country. If you prefer to freshen up before lunch, return to the hotel and then take a leisurely stroll to either Zim’s Cafe or Stella’s Kentucky Deli, both popular local favorites that pride themselves on sourcing their ingredients locally.
Day 1: Afternoon
1:30 p.m.: Just a short walk away, next door in fact, lies the Lexington Visitors Center, housed within the iconic old courthouse (the same building as Zim’s Cafe). Here, you can acquire maps for a self-guided walking tour and delve into the city’s history through informative displays. More importantly, the friendly staff can provide you with valuable information about upcoming events and festivals. During pleasant weather, Lexington is often alive with outdoor events, many of which are free, providing opportunities to enjoy local bands and mingle with welcoming residents.
2 p.m.: How you spend your afternoon depends on your personal interests. For a swift introduction to the nearest bourbon distillery, head to the Lexington Brewing Company or the James E. Pepper Distilling Company, both conveniently located within city limits and offering guided tours of their distilling operations.
For those with a keen interest in Lexington‘s history, free audio guides for walking tours are available on the Lexington Public Library website. Begin your journey by walking down Main Street to tour the Mary Todd Lincoln House, where the First Lady resided until 1839. Subsequently, meander through Gratz Park, a charming neighborhood that was once home to some of Lexington‘s most prominent residents in the 1800s. Continue your exploration by wandering the grounds of Transylvania University, established in 1780 as the first college west of the Allegheny Mountains. The best part? All of these historical sites are within a 10-minute walk of your hotel!
5 p.m.: By walking 20 minutes in the opposite direction, past the old courthouse, and onward to Thoroughbred Park at the intersection of Main Street and Midland Ave, you can claim to have experienced Lexington‘s compact and charming downtown area from end to end. The bronze art installation featuring jockeys racing atop life-size horses provides a perfect photo opportunity. On your way back to the hotel, take a moment to admire some of Lexington‘s impressive street murals, adding a touch of contemporary art to the historical landscape.
Day 1: Evening
6 p.m.: Kick off your evening by exploring the captivating art within your own hotel, if you haven’t already done so. Grab a pre-dinner drink from Lockbox, the hotel’s bar and restaurant, and sip it while you wander through the lobby and second-floor galleries.
7 p.m.: Next, choose from Lexington‘s many outstanding dining establishments. Dudley’s on Short has been a culinary institution since 1981. For Italian cuisine in a lively atmosphere, try ItalX, or for a prime steak experience, Tony’s of Lexington is an excellent choice. If you’re in the mood for authentic French cuisine and highly-rated mussels, secure a sidewalk table at Le Deauville on North Limestone. For a more casual dining experience, there are numerous reasonably priced eateries in the neighborhood.
11 p.m.: Before heading to your room for the night, observe the large, glowing orbs hanging inside Lockbox. If they are blue and yellow, you can anticipate a sunny day tomorrow. If they are gray, be sure to pack an umbrella!
Day 2: Morning
On Saturdays: Start your day by taking a stroll through Lexington‘s Saturday Farmers Market, located next to the old courthouse. The atmosphere is lively and pleasant, and you can grab a coffee while browsing art and local products. Musicians from the Lexington Philharmonic and other performers often grace the market with their talents.
8:30 a.m.: If you’re visiting Lexington in April or October, when the races are running at Keeneland, your entertainment for the day is practically predetermined. However, even if it’s not race season, you should still make time to visit this internationally renowned racecourse. The general public is invited to enter for free to watch the early morning training runs from 6 a.m. to 10 a.m. This provides an opportunity to see jockeys, trainers, and thoroughbreds at work in an informal setting. Paid tours are available, or you can simply explore the beautiful venue at your own pace.
11 a.m.: If you plan to return to Keeneland later for the races, eat a hearty lunch outside of Keeneland to keep you going until dinner. Drive over to Malone’s in Palomar or Ramsey’s Diner on Old Harrodsburg Road. Both are popular local chains enjoyed by Lexingtonians. If you’re feeling adventurous, try a Hot Brown, a famously delicious but rich Kentucky creation. The one at Ramsey’s is a local favorite.
Day 2: Afternoon
1 p.m.: The horse racing experience at Keeneland is a cultural phenomenon that must be witnessed firsthand. Don’t worry if you’re not a betting enthusiast; many visitors never even place a wager. The grounds and pageantry are breathtaking, and the atmosphere of reverence as horses are presented in the paddock between races will likely become a highlight of your trip to Lexington. Gates open at 11 a.m., and the first race commences at 1:05 p.m.
For those seeking outdoor enjoyment in a setting other than Keeneland, consider driving to the UK Arboretum, Kentucky’s state botanical garden. You can embark on a hike or simply admire the impressive horticultural displays. Entrance is free. Another great option for local history is Ashland, the Henry Clay Estate, former residence of the ninth U.S. Secretary of State. Wandering the beautifully manicured grounds is free, but for a truly immersive experience, take a one-hour tour of the mansion to see how the famous statesman lived in the 1800s. If you desire air conditioning after a hot afternoon of walking, the University of Kentucky Art Museum is free and only five minutes away.
4 p.m.: Whatever you choose to do, make sure to beat the Keeneland traffic! Since you’ll be on the south end of Lexington after the races, stop in at Joseph-Beth Booksellers in Lexington Green to browse the extensive collection of books by local authors. For more local souvenirs, Artique (located in Fayette Mall across the street) sells beautiful gifts and artwork created by Kentucky artists. Additional shopping opportunities, primarily upscale, are available at The Summit at Fritz Farm, located a short distance away.
Day 2: Evening
7 p.m.: Head back downtown to begin celebrating your Keeneland winnings (or forgetting your losses). Start with some small plates and top-shelf tequila at Corto Lima, a perpetually busy downtown establishment with sidewalk seating. Alternatively, grab one of the exquisite charcuterie boards and a delicious cocktail at The Grove, a cozy outdoor spot tucked behind Harvey’s Bar. If the University of Kentucky is playing basketball, expect a lively scene throughout the city as passionate fans gather to cheer for their Wildcats.
9 p.m.: Get serious about celebrating with one of the Instagram-worthy cocktails from Pour Decisions on East Main Street. If you prefer your bourbon neat, step inside Bourbon on Rye. Live music venues are plentiful in the area. North Limestone is lined with additional eateries and bars, including Minglewood, a spot known for late-night food (until 11 p.m.) and craft cocktails.
In the morning, if you have time to spare before your flight or need some assistance recovering, return to Keeneland one last time. Lexington‘s Blue Grass Airport is conveniently located just across Versailles Road. Take the road next to Barn 20 until it ends at the Keeneland Track Kitchen, a Lexington "secret" where you can enjoy a hearty, inexpensive breakfast while engaging in some interesting people-watching. You’ll often be joined by famous trainers, owners, and jockeys!
