Discover the Bluegrass over four days and three nights filled with Lexington’s most iconic experiences, from legendary horse country and historic landmarks to vibrant local dining and scenic countryside drives. This itinerary brings together the region’s signature attractions and authentic cultural touchpoints, offering a balanced and immersive way to experience the Horse Capital of the World and its surrounding communities.
Day 1
Pictured: Kentucky Horse Park
11:00 am | Welcome to Lexington! Check in at one of Lexington's group-friendly hotels.
12:00 pm | Enjoy a buffet-style lunch in a private dining room at Bluegrass Luncheon, located at the Kentucky Horse Park. Available to groups of 15 or more.
1:30 pm | Spend the day exploring the Kentucky Horse Park, a 1,200-acre Kentucky State Park dedicated to humanity's relationship with the horse. Visitors can find 30 breeds showcased through daily equine presentations, horse-drawn tours and carriage rides, world-renowned museums, horseback riding, and a comprehensive schedule of equestrian events throughout the year.
5:30 pm | Return to your hotel.
6:30 pm | Enjoy dinner at one of Lexington's fine restaurants. Bella Notte features full-service dining and a rustic Italian menu highlighting fresh, local, and seasonal ingredients. In the heart of downtown, Dudley's on Short offers elegant private dining spaces paired with outstanding service and refined cuisine. For a lakeside dining experience, Palmers Fresh Grill serves fresh seafood alongside an award-winning wine list.
Day 2
Pictured: Ashland - The Henry Clay Estate
8:30 am | Have breakfast at your hotel.
10:00 am | Take a scenic drive through Lexington's world-famous Horse Country, where rolling pastures and iconic white fences define the landscape. Visit a working Thoroughbred farm, such as Claiborne Farm or Mill Ridge Farm, for a behind-the-scenes look at Kentucky's equine industry and the places where champions are bred and raised.
12:00 pm | Enjoy lunch at a regional restaurant.
2:00 pm | Step back in time with a tour of one of Lexington's historic homes, such as Ashland - The Henry Clay Estate, the Mary Todd Lincoln House, or Waveland State Historic Site. Each offers a unique glimpse into the people, architecture, and stories that helped shape the history of Lexington and Kentucky.
4:00 pm | Stop at Gatton Park on the Town Branch, a dynamic green space in the heart of downtown Lexington, offering events, programming, concerts, and inviting amenities. While you're there, be sure to snap a photo with Big Lex, a custom 12-foot-tall installation celebrating the local Thoroughbred legend, Lexington.
5:30 pm | Enjoy dinner at one of Lexington's group-friendly restaurants featuring local flavors and Kentucky specialties. A Lexington tradition, Merrick Inn has been serving classic Kentucky fare and warm Southern hospitality for generations, with its fried chicken dinner earning a devoted following among locals and visitors alike. For bourbon-inspired dining, Carson's Food & Drink offers Kentucky favorites alongside an extensive bourbon selection in a lively, upscale setting.
7:30 pm | Return to your hotel.
Day 3
Pictured: Keeneland
7:00 am | Depart for Keeneland Racecourse. This national historic landmark serves as the world's largest Thoroughbred auction house and hosts world-class racing twice a year in April and October.
7:30 am | Begin the day at Keeneland with a behind-the-scenes experience at one of the world's most celebrated Thoroughbred racecourses. The Sunrise Tour provides exclusive access to watch morning training from premier viewing locations, while the Morning Works Tour offers an insider's look at Keeneland's history, traditions, and beautiful grounds as horses prepare for the day ahead. After the tour concludes, check out The Keeneland Shop for specialty apparel, souvenirs, and gifts for every occasion.
8:45 am | Round out your Keeneland experience with breakfast at the Keeneland Track Kitchen, one of Lexington's best-kept dining gems. Rub elbows with trainers, jockeys, and horsemen while enjoying a hearty Southern breakfast.
9:45 am | Travel to Williamstown for a day exploring the Ark Encounter, featuring a life-size replica of Noah's Ark. Guests can explore three decks of exhibits that offer a glimpse into what life aboard the ark may have been like, with engaging displays depicting the animals, people, and daily activities associated with the biblical account.
4:00 pm | Return to your hotel.
6:30 pm | Dinner at one of Lexington's award-winning restaurants. Located in The Summit at Fritz Farm, Honeywood, owned by local restaurateur Ouita Michel, is known for its sweet potato beignets, locally sourced meats and produce, and creative Southern cuisine. For a refined yet approachable group dining experience, Tony’s of Lexington offers an upscale steakhouse menu in an elegant setting, featuring premium cuts, fresh seafood, and an extensive wine list.
Day 4
Pictured: Buffalo Trace Distillery
8:00 am | Breakfast at your hotel.
9:00 am | Head to Frankfort for a visit to Buffalo Trace Distillery, the oldest continuously operating distillery in America. Situated along the banks of the Kentucky River, this National Historic Landmark has been crafting award-winning spirits for more than 200 years. Tour the historic campus, learn about the bourbon-making process, and discover the stories behind renowned brands such as Buffalo Trace, Eagle Rare, E.H. Taylor Jr., Blanton's, and the celebrated Van Winkle collection.
11:00 am | Enjoy lunch at Buffalo Trace Distillery’s newly opened John G. Carlisle Café, where made-to-order sandwiches, fresh salads, desserts, and Kentucky-inspired classics are served in a relaxed, casual setting. Surrounded by the distillery’s historic grounds, it’s the perfect place to refuel before continuing on to your next adventure.
