Top 6 Things To Do This Winter In Lexington, Kentucky

 

 

Worried there won’t be much to do in the Bluegrass when the bluegrass isn’t really bluegrassing? You shouldn’t be. Lexington is every bit as lovely and lively in the winter as it is the rest of the year, with plenty of seasonal events and attractions to make you feel all warm and fuzzy inside. Here’s a few of our favorites.

 

1. See a Different Side of Horse Country

Pictured here: Denali Stud Farm

Lexington is the Horse Capital of the World all year round. You can always take a leisurely drive by the beautiful snow-dusted pastures on your own, but Visit Horse Country can take you behind the scenes at many of Lexington’s iconic horse farms to meet racing’s superstars. Both Keeneland and the Kentucky Horse Park become winter wonderlands for horse lovers. Stay indoors and get a look at how champion Thoroughbreads are fueled at Hallway Feeds. And winter is also a great time to check out Lexington’s lesser known but vitally important equine care facilities like Hagyard Equine Medical Institute, the Secretariat Center, and New Vocations Racehorse Adoption Program. Just check online or call ahead for tour availability.

 

2. Experience Bourbonland on the Rocks

Pictured here: Bourbon on Rye

Beneath Lexington’s rolling bluegrass hills, a rare limestone formation filters natural spring water for the world’s finest bourbon, fueling a magical culture of creativity and innovation that we call Bourbonland. What better time to immerse yourself in that culture and feel that warm “Kentucky Hug” than the cold of winter? Enjoy tours and tastings at 18 nearby bourbon distilleries, sample rare bottles and inventive cocktails at world-class bourbon bars, and let the Kentucky Bourbon Trail guide you deep into the countryside for a look at the history and craft of America’s native spirit that can’t be found anywhere else.

 

3. Shop for Yourself or Someone Special

Pictured here: Syers Browning, Located in the Warehouse Block

Filled with quaint boutiques and large-scale shopping centers, Lexington is a retail paradise where you’re sure to find exactly what you’re looking for. Unique districts like Chevy Chase, Distillery District, Warehouse Block, Southland, Downtown, and Greyline Station are filled with independent shops, bars and restaurants to take the stress out of your search. Hamburg Pavilion, the Summit at Fritz Farm and Fayette Mall are your best bets for finding big brands. And don’t forget about the Lexington Visitors Center. Our Gift Shop has apparel, keepsakes and more for the Lexington lover in your life.

 

4. Eat & Drink (Then Eat & Drink Some More)

Pictured here: The Obstinate Sons, Located in Chevy Chase

Home to multiple James Beard Award-nominated chefs and recognized as a Top 20 Culinary City in the South by The Local Palate, Lexington’s dedication to farm-to-table dining and a vibrant culinary scene have solidified its position as a must-visit destination for food lovers. No matter what you're craving—from international cuisine to comforting Southern classics—Lexington has a restaurant that'll hit the spot. Warm up with a seasonal coffee from shops like The Greenery, Lussi Brown, Kenwick Table, and Manchester Coffee Co. Then grab a table at world-class restaurants like Granddam at The Manchester Hotel, Holly Hill Inn, Dudley’s on Short, Lockbox, Italx and Corto Lima. Find more places to indulge this winter on our Restaurants page.

 

5. Warm Up to Lexington’s Rich History

Pictured here: Mary Todd Lincoln House

Winter is the perfect time to reflect upon Lexington’s fascinating history and alluring architecture. Take a candlelight tour of Ashland, the meticulously preserved estate of 19th century statesman Henry Clay. The Mary Todd Lincoln House, childhood home of the former first lady, is like a time capsule of a bygone era. Waveland and Shaker Village of Pleasant Hill are both gems of historic architecture that host special holiday events. And LexHistory, formerly the Lexington History Museum, offers a fantastic overview of the city’s most notable people, places and happenings.

 

6. Relax and Recharge In Lexington’s Cozy Hotels

Pictured here: The Manchester Hotel

After a long, hectic year, sometimes you just need to recharge your batteries. Lexington has a host of hospitable boutique hotels where you can relax before exploring the city or simply lounge the day away in style. The Manchester (who was named “One of TIME’s World's Greatest Places” in 2024), 21c Museum Hotel, Elwood, The Sire and Origin all offer elevated accommodations and amenities inspired by Bluegrass culture. As a convenient bonus, each has its own restaurant and bar—consistently rated among the best in Lexington—where you can enjoy fine dining and seasonal cocktails without ever leaving the lavish comfort of your cozy winter retreat.

Find more local lodging and book your stay today on our Hotels page.

 

BONUS: Just for the Holidays

Pictured here: Kentucky Horse Park

With special events throughout winter, Lexington can put any Scrooge or Grinch in a festive mood. Join us as we officially kick off the Holiday Season with the annual Christmas Tree Lighting in Triangle Park, which boasts a family-friendly ice skating rink from early November through January. Southern Lights is a three-mile driving tour of twinkling lights. Christmas at Mustard Seed Hill is a spectacular holiday tradition in Millersburg, Kentucky, just 30 minutes north of Lexington. Take part in a Christmas by Candlelight tour at historic Shaker Village of Pleasant Hill to gain a deeper understanding of the history of Christmas celebrations in America. And what could make your Holiday more magical than brunch with Santa at The Kentucky Castle?

Holiday programming also takes center stage at the historic Lexington Opera House every winter. This year, catch Christmas classics performed by Mannheim Steamroller against a dazzling multimedia backdrop. Or a hilarious stage adaptation of the wildly popular holiday movie, A Christmas Story. And don’t miss The Nutcracker. This holiday tradition is an enchanting production featuring brand new choreography and the Tschaikovsky score you know and love. So get your tickets and we’ll see you at the show!