Discover the Charm of Lexington: A Traveler's Guide to Historic Landmarks and Hidden Gems

Advisor - Gillian Spatz
Curated By

Gillian Spatz

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  • City Travel

  • Kentucky

  • History

  • Sightseeing

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Curator’s statement

Nestled in the heart of Kentucky, Lexington beckons travelers with its rich tapestry of history, vibrant culture and picturesque landscapes. From the storied grounds of the Kentucky Horse Park to the quaint streets of downtown, Lexington offers a captivating blend of old-world charm and modern allure. Whether you're a history buff exploring the fascinating past of the Bluegrass State or an outdoor enthusiast eager to roam the scenic trails of the Red River Gorge, Lexington promises an unforgettable journey filled with memorable experiences and endless surprises. Join us as we embark on a virtual tour of this enchanting city, where every cobblestone pathway and rolling hill invites adventure and discovery.

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Where to stay in Lexington

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21c Museum Hotel Lexington

21c Museum Hotel Lexington combines contemporary art, boutique accommodations, and culinary excellence in the heart of downtown Lexington, Kentucky.

Elwood Hotel & Suites

Adventure-inspired hotel with boho furnishings and a laidback vibe.

The Sire Hotel Lexington, Tapestry Collection by Hilton

Discover Southern charm and modern elegance at this boutique hotel, where stylish design meets warm hospitality, offering a unique stay in the heart of Lexington.

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Things to do in Lexington

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  • Tour the Kentucky Horse Park: Explore the world of horses at this renowned equine-themed park, featuring museums, horse shows and horse farm tours showcasing the beauty and history of Kentucky's horse industry.

  • Visit Keeneland Racecourse: Experience the thrill of horse racing at one of the most iconic racetracks in the country. Keeneland hosts live Thoroughbred racing meets in the spring and fall, as well as year-round sales and events.

  • Explore the Bourbon Trail: Embark on a tasting tour of Lexington's famous bourbon distilleries, such as Woodford Reserve, Buffalo Trace and Wild Turkey. Learn about bourbon production and sample a variety of Kentucky's finest spirits.

  • Stroll through the Arboretum: The University of Kentucky Arboretum offers 100 acres of gardens, walking trails and educational exhibits, showcasing a diverse collection of native and exotic plants.

  • Discover the Legacy Trail: This 12-mile paved trail connects downtown Lexington with the Kentucky Horse Park, providing opportunities for walking, running, biking and exploring the scenic beauty of the Bluegrass region.

  • Tour Historic Homes and Gardens: Explore Lexington's rich history and architecture by visiting historic homes and gardens such as Ashland: the Henry Clay Estate and the Waveland State Historic Site.

  • Attend a University of Kentucky sporting event: Cheer on the Wildcats at a basketball game in Rupp Arena or catch a football game at Kroger Field. University of Kentucky sports events offer an exciting atmosphere and a chance to experience the local sports culture.

  • Shop & dine in downtown Lexington: Discover unique boutiques, art galleries and restaurants in downtown Lexington's vibrant shopping and dining district. Enjoy farm-to-table cuisine, craft cocktails and live music in the heart of the city.

  • Explore the Lexington Distillery District: This revitalized area is home to craft breweries, distilleries, restaurants and art galleries, offering a lively atmosphere and plenty of opportunities for entertainment and exploration.

  • Take a guided tour of Thoroughbred Horse Farms: Experience the beauty of Kentucky's Bluegrass countryside on a guided tour of Thoroughbred horse farms, where you can see champion racehorses and learn about the breeding and training process.

Places to eat & drink in Lexington

Potatoes and meat in a white bowl.
  • Dudley's on Short: Located in a historic building downtown, Dudley's on Short offers upscale American cuisine with a focus on locally sourced ingredients. The menu features seasonal dishes and an extensive wine list.

  • Malone's: Known for its prime steaks and seafood, Malone's is a popular choice for fine dining in Lexington. The restaurant also offers a selection of signature cocktails and an extensive wine cellar.

  • Holly Hill Inn: Located in nearby Midway, Holly Hill Inn offers upscale Southern cuisine in a charming historic setting. The menu features seasonal ingredients and classic dishes with a modern twist.

  • Lockbox: Situated in the 21c Museum Hotel, Lockbox offers contemporary American cuisine with a focus on locally sourced ingredients. The restaurant's sleek, modern design complements its innovative menu.

  • Blue Door Smokehouse: For authentic barbecue, head to Blue Door Smokehouse. This casual eatery serves up mouthwatering smoked meats, including brisket, ribs, pulled pork and sausage, along with classic sides like macaroni and cheese and baked beans.

  • Palmers Fresh Grill: Known for its fresh seafood and Southern-inspired dishes, Palmers Fresh Grill offers a diverse menu featuring everything from oysters and shrimp to steak and pasta, all prepared with locally sourced ingredients.

  • Azur Restaurant & Patio: Offering Mediterranean-inspired cuisine with a Southern twist, Azur Restaurant & Patio features a menu of fresh seafood, pasta and grilled meats, as well as an extensive wine list and creative cocktails.

  • Smithtown Seafood: Located in the popular Lexington Distillery District, Smithtown Seafood offers a casual dining experience with a focus on sustainable seafood. Guests can enjoy fish tacos, shrimp po'boys and other seafood favorites in a relaxed atmosphere.

Need to Know

Looking for more travel inspiration? Check out my guide, Experience San Antonio: A Comprehensive Guide to the City's Must-See Attractions and Hidden Gems. This guide is part of our ongoing series on travel to Kentucky.

Advisor - Gillian Spatz

Travel Advisor

Gillian Spatz

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