It's a fact—nearly 100% of travelers visit Lexington, Kentucky, for a day or two and immediately regret the decision. They wish they had planned to stay longer. A weekend just isn't enough time to fully experience the sublime bluegrass landscape, rich bourbon-infused culture, and treasure trove of hidden gems that make Lexington one of the "Top 5 Best Small Cities in the U.S." according to Condé Nast Traveler. Give serendipity room to work its magic and book a three-day getaway in Lexington, Kentucky—Horse Capital of the World. Otherwise, you may experience these five common regrets:

"A weekend just isn't enough time to fully experience the treasure trove of culture, landscape and hidden gems that make Lexington one of the Top 5 Best Small Cities in the U.S. according to Condé Nast Traveler."

You won't find a more beautiful backdrop for your getaway than Lexington. A 15-minute drive in any direction from downtown will transport you to a sublime landscape of rolling bluegrass hills and fence-lined pastures unlike any in the world. The key to understanding Lexington is to understand the land that surrounds it—beautiful rolling hills contoured by pristine fence-lined horse farms, with abundant rivers and streams carving the land. For a quintessential Bluegrass experience, book a Horse Country Tour and get exclusive access to some of the 450 picture-perfect horse farms in the area. Or join thousands of fans for a race day at Keeneland, where Kentucky’s unique Thoroughbred traditions come to life. Can’t make race day? Take a guided tour—or rub elbows with jockeys, owners and trainers over a hearty Southern breakfast at the Track Kitchen. The Kentucky Horse Park is another can't-miss for horse lovers, home to nearly 50 breeds that graze its 1,200 acres of lush bluegrass pastures. You can meet them, go for a ride, explore interactive museums, or even camp on-site. The best views of the Bluegrass are waiting for you just minutes from downtown. And there’s no better way to experience our legendary landscape than by driving or cycling the country roads around Lexington. Take the scenic route with the Bluegrass Country Driving Tour, a self-guided route that takes you past storied farms, charming neighborhoods, and beautiful countryside.

1. You'll be bitter you didn't get to know the real Bluegrass.

There's no better city for bourbon lovers than Lexington, Kentucky: Bourbonland. With 16 nearby distilleries within 45 minutes, including industry icons like Woodford Reserve, Buffalo Trace, Wild Turkey, and Four Roses, Lexington is the perfect place to maximize your bourbon experience. Lexington is pushing the bourbon industry forward with newcomers like Fresh Bourbon, the first Black-owned bourbon distillery, and experimental distillers like RD1. Bourbon creativity abounds at Lexington’s iconic bar scene, with knowledgeable mixologists incorporating the spirit into delicious craft cocktails at notable spots like Bourbon on Rye and Lost Palm. Just outside downtown, you'll find the Distillery District—a revitalized historic area that's home to the recently-renovated James E. Pepper Distillery and a one-stop shop for food, drinks, shopping and entertainment. For bourbon hunters, local retailers and boutique shops often have rare expressions that can't be found anywhere else.

2. You'll be bummed you didn't venture into Bourbonland.

Lexington's food scene is a feast for the senses that you won't want to rush through. The city has earned its reputation as a culinary powerhouse, boasting multiple James Beard Award-nominated chefs and recognition as a Top 20 Culinary City in the South. The farm-to-table movement flourishes here, with chefs drawing inspiration from the fertile Bluegrass Region. Morning people will delight in locally roasted coffees paired with fresh-baked pastries, while brunch enthusiasts can toast with mimosas alongside innovative breakfast creations. Stop and browse through the bustling Lexington Farmers Market after breakfast to stock up on baked goods, fresh produce, flowers, and local beer and wine. Casual dining spots showcase the diversity of Lexington's culinary landscape, from mouthwatering BBQ to authentic global cuisines. Fine dining establishments offer curated cocktail lists and refined menus that both refresh and expand your palate. For an elevated take on the region’s distinct cuisine, treat yourself to a meal at one of Chef Ouita Michel’s famous restaurants. Don't forget to save room for dessert. Lexington's bakeries and ice cream shops serve up both timeless favorites and inventive new flavors that provide the perfect finale to any meal. You'll need more than a weekend to truly savor the breadth of culinary delights that make Lexington a foodie paradise.

3. You'll wish you saved room for seconds.

By StoryStudio on March 26, 2025

There are 16 bourbon distilleries within 45 minutes of Lexington’s charming downtown.

Plan your ultimate three-day Lexington getaway at VisitLEX.com.

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Lexington has a vibrant creative culture that’s a feast for the senses. Here you'll find eclectic art galleries, dozens of murals, festivals, live music, theaters, and a progressive population that pours their hearts into making the city a living, breathing work of art. The city has a surprising variety of music venues, from the iconic 20,000+ seat Rupp Arena to the historic Lexington Opera House and Kentucky Theatre. For more intimate experiences, visit The Burl in the Distillery District or Tee Dee's Lounge, the legendary East Side nightclub where blues guitar virtuoso Tee Dee Young has been dazzling guests for over 30 years. Lexington is also home to more than 50 large-scale street art murals that transform our neighborhoods into thought-provoking outdoor galleries. Download the Lexington Mural Challenge Pass to map your route and earn a poster after you visit six murals. Our city’s rich history is also evident in its well-preserved architecture. Historic neighborhoods like Gratz Park exude the same charm they did nearly 200 years ago. Experience the "Athens of the West" through Historic Downtown Walking Tours or the African American Heritage Self-Guided Walking Tour that illuminates the extraordinary yet often overlooked people who shaped the city. With such a rich cultural tapestry, you'll need more than a weekend to truly immerse yourself in Lexington's creative spirit.

4. You’ll kick yourself for not soaking up more culture.

Lexington has distinct districts that bring their own authentic flavor to the visitor experience, each offering unique restaurants, retailers, and vibes to fit your style. Anchored by the iconic Chevy Chase Inn (CCI), Lexington's oldest bar, the historic Chevy Chase neighborhood is one of the city's oldest. The Distillery District features bourbon distilleries, restaurants, and The Manchester boutique hotel in a revitalized 25-acre walkable area dating back to 1879. Greyline Station, a former Greyhound bus depot built in 1928, is now a Northside icon filled with locally owned eateries and retailers. Southland Drive, known as "Lexington's Music Row," spans a mile-long stretch of eclectic locally owned businesses. The fast-growing Warehouse Block lends its century-old industrial character to an array of independent businesses, casual and upscale dining, vintage shops, and locally made beverages from craft beer to sake. And The Summit at Fritz Farm is a true one-stop shop with around 70 retailers, from local boutiques and to the world’s trendiest brands, as well as a variety of dining options. Exploring these diverse districts requires more than just a weekend—it demands the luxury of time that only an extended stay can provide.

5. You'll be sorry you stuck to the beaten path.

So what are you waiting for? Hurry up and take it slow. Plan your ultimate three-day Lexington getaway at VisitLEX.com.

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