5-day Trip to Lexington, Kentucky Itinerary

Start your day with a visit to Kentucky Horse Park, a working horse farm and educational theme park. Take a guided tour to learn about the history of thoroughbred racing and see the beautiful horses up close. Afterward, stop by Windy Corner Market for a delicious brunch.

Embark on a scenic drive along the Bluegrass Scenic Byway, which will take you through the picturesque horse farms of the Bluegrass region. Stop by Claiborne Farm, one of the world's leading thoroughbred farms, for a guided tour. End the afternoon with a visit to Woodford Reserve Distillery for a bourbon tasting.

Head back to downtown Lexington and enjoy dinner at Tony's of Lexington, a classic steakhouse known for its prime cuts of meat. After dinner, relax at Belle's Cocktail House, a stylish lounge offering a wide selection of handcrafted cocktails.

Take a day trip to Louisville, located about 80 miles west of Lexington. Start your day with a visit to the Kentucky Derby Museum, where you can learn about the history of the iconic horse race. Afterward, grab a quick bite at Please & Thank You, a popular coffee shop and record store.

Explore the vibrant Muhammad Ali Center, a museum dedicated to the life and legacy of the legendary boxer Muhammad Ali. Afterward, enjoy a delicious lunch at Doc Crow's Southern Smokehouse & Raw Bar, known for its Southern cuisine and seafood.

Take a leisurely stroll along Fourth Street Live!, a bustling entertainment district with restaurants, bars, and live music venues. Enjoy dinner at MilkWood, a restaurant offering a fusion of Southern and Asian flavors. End the evening with a visit to Haymarket Whiskey Bar, a popular spot for bourbon enthusiasts.

Start your day with a hike at the Raven Run Nature Sanctuary, a 734-acre nature preserve with scenic trails and diverse wildlife. Afterward, head to Magee's Bakery for a delicious pastry or sandwich.

Visit the Kentucky River Palisades, a stunning natural area with towering cliffs and hiking trails. Enjoy a picnic lunch at one of the scenic overlooks. Afterward, explore the Lexington Distillery District, home to several craft breweries, distilleries, and unique shops.

Indulge in a farm-to-table dining experience at Lockbox, located in the 21c Museum Hotel. After dinner, visit The Burl, a live music venue known for its intimate atmosphere and diverse lineup of artists.

Take a day trip to Cincinnati, located about 85 miles north of Lexington. Start your day with a visit to the Cincinnati Art Museum, which houses an extensive collection of artworks from various periods and cultures. Afterward, enjoy brunch at Sleepy Bee Cafe, known for its creative and delicious dishes.

Explore the historic Findlay Market, a vibrant public market with a wide variety of vendors selling fresh produce, meats, and local products. Afterward, visit the National Underground Railroad Freedom Center, a museum dedicated to telling the stories of freedom seekers and abolitionists.

Enjoy dinner at Sotto, a popular Italian restaurant known for its homemade pasta and cozy atmosphere. Afterward, catch a show at the Taft Theatre, a historic theater known for its Broadway productions and live performances.