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5-day Adventure in Lexington Itinerary

Published: 2023 Oct 08

Exploring the Heart of Lexington

Morning

Start your day with a delicious breakfast at Stella's Kentucky Deli, known for its Southern comfort food and homemade biscuits. After breakfast, head to the Kentucky Horse Park to immerse yourself in the equestrian culture. Explore the museum, watch horse shows, and even take a guided tour of the stables.

Afternoon

For lunch, visit Coles 735 Main, a local favorite known for its farm-to-table cuisine. Afterward, take a stroll through the picturesque Ashland, The Henry Clay Estate, the former home of statesman Henry Clay. Learn about his life and influential political career while enjoying the beautiful gardens.

Evening

Indulge in a fine dining experience at Dudley's on Short, where you can savor modern American cuisine in an elegant setting. After dinner, head to The Burl Arcade for an evening of live music and entertainment.

Bedtime

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Bourbon and History

Morning

Start your morning with a visit to Woodford Reserve Distillery for a guided tour of their historic bourbon distillery. Learn about the bourbon-making process and sample some of their finest spirits. After the tour, enjoy a coffee and pastry at A Cup of Common Wealth.

Afternoon

For lunch, try OBC Kitchen, a gastropub known for its creative dishes and extensive bourbon selection. Afterward, explore the Mary Todd Lincoln House, the childhood home of Abraham Lincoln's wife. Take a guided tour to learn about her life and the history of the house.

Evening

Enjoy a delicious dinner at Lockbox, located in the 21c Museum Hotel. This contemporary restaurant offers a unique dining experience with its rotating menu of seasonal dishes. After dinner, head to Manchester Music Hall for a night of live music and dancing.

Bedtime

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Outdoor Adventures

Morning

Start your day with a hike at Raven Run Nature Sanctuary. Explore the scenic trails, enjoy breathtaking views, and spot wildlife along the way. After your hike, grab a quick snack at Rolling Oven, a local pizzeria known for its wood-fired pizzas.

Afternoon

For lunch, visit Cole's 735 Main, a popular spot for its delicious sandwiches and salads. Afterward, head to the Kentucky River Palisades State Park for a relaxing afternoon of kayaking or canoeing. Enjoy the serene beauty of the river and surrounding cliffs.

Evening

Indulge in a hearty dinner at Coles 735 Main, where you can enjoy comfort food classics like fried chicken and mac 'n' cheese. After dinner, head to West Sixth Brewing for a taste of Lexington's craft beer scene.

Bedtime

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Arts and Culture

Morning

Start your day with a visit to the Lexington Opera House. Take a guided tour of this historic theater and learn about its rich history and architecture. Afterward, enjoy a coffee and pastry at A Cup of Common Wealth.

Afternoon

For lunch, try Coles 735 Main, a local favorite known for its farm-to-table cuisine. Afterward, explore the Lexington Art League. Admire the contemporary art exhibits and maybe even participate in a workshop or event.

Evening

Enjoy a delightful dinner at Limestone Blue, a charming restaurant specializing in Southern cuisine with a modern twist. After dinner, head to The Burl Arcade for an evening of live music and entertainment.

Bedtime

Find amazing hotels in Lexington, Kentucky.

Historic Sites and Shopping

Morning

Start your morning with a visit to the Mary Todd Lincoln House, the childhood home of Abraham Lincoln's wife. Take a guided tour to learn about her life and the history of the house. Afterward, enjoy a coffee and pastry at A Cup of Common Wealth.

Afternoon

For lunch, visit OBC Kitchen, a gastropub known for its creative dishes and extensive bourbon selection. Afterward, explore the Ashland, The Henry Clay Estate, the former home of statesman Henry Clay. Learn about his life and influential political career while enjoying the beautiful gardens.

Evening

Indulge in a fine dining experience at Lockbox, where you can savor modern American cuisine in an elegant setting. After dinner, head to The Burl Arcade for an evening of live music and entertainment.

Bedtime

Find amazing hotels in Lexington, Kentucky.