Lexington is a wonderland of winter fun. The city’s famous year-round attractions get a dose of holiday cheer, and a sleigh full of special seasonal events make the Bluegrass more magical than just about any other time of year. Here’s how to do it right.
1. Pick Up Tickets for a Holiday Show
Pictured here: The Nutcracker at the Lexington Opera House
Holiday programming takes center stage at the historic Lexington Opera House every winter. This year, catch Kentucky Ballet Theatre’s The Nutcracker, Dolly Parton’s Smoky Mountain Christmas Carol, and Alltech’s Celebration of Song at the Kentucky Horse Park.
Other performances to get you in the holiday spirit include Rudolph the Red-Nosed Reindeer at the Lexington Children's Theatre, Collage: A Holiday Spectacular at the University of Kentucky Singletary Concert Hall, and Slay Bells Holiday Drag & Variety Show Spectacular at the Lyric Theatre. Get your tickets today and we’ll see you at the show!
2. Shop for Yourself or Someone Special
Pictured here: Wreaths at the Kentucky Native Cafe Christmas Market
Brimming with eclectic boutiques like Poppy & Pomelo and large-scale shopping centers, Lexington is a retail paradise where you’re sure to find exactly what you’re looking for. Unique districts and neighborhoods like Chevy Chase, the Distillery District, the Warehouse Block, Southland, and Downtown 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—the largest mall in Kentucky—are your best bets for finding big brands. Be sure to stop by The Keeneland Shop to browse a diverse selection of equine-inspired gifts for every horse lover on your list. While you’re there, get a behind-the-scenes look at Lexington’s famous Keeneland Racecourse with Morning Works and guided tours offered year-round.
For handmade items perfect for gifting, don’t miss the Crafted Social Winter Market at Greyline Station and the Kentucky Native Café Christmas Market at Michler’s. And don’t forget about the Lexington Visitors Center. Our Gift Shop has apparel, exclusive Blue Horse merch, keepsakes, and more so you can “Give a Little Lex” to your loved ones this holiday season.
3. Feel That Comforting Hug of Kentucky Bourbon
Pictured here: Tasting experience at Fresh Bourbon
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? Sample rare bottles and inventive cocktails at world-class bourbon bars, follow the Kentucky Bourbon Trail from city center to the countryside, and immerse yourself in the history and craft of America’s Native Spirit with tours and tastings at 18 nearby bourbon distilleries, including seven within a mile of Downtown and many more close by. Many even go all out with beautiful holiday decorations all across their facilities. Be sure to pick up a bottle of something special on your journey—and a box of Kentucky’s signature holiday treat, bourbon balls, invented by Ruth Hunt—as a thoughtful gift for someone on your “nice” list.
Just in time for the holidays, we've launched the Bourbonland Tasting Pass, your exclusive gateway to experiencing the best of the region’s bourbon scene. Whether you're a seasoned enthusiast or simply bourbon-curious, this pass lets you explore and savor tasting flights from some of the region’s finest distilleries at your own pace. The Pass unlocks delicious flights from Barrel House Distilling Co., Bespoken Spirits, Bluegrass Distillers, Dark Arts Whiskey House & Alchemy Lab, Fresh Bourbon Distillery, and James E. Pepper Distillery. A perfect gift for yourself or the bourbon lover in your life!
4. Let Lexington Light Up Your Holidays
Pictured here: Legendary Festival of Lights at Legends Field
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 at Luminate Lexington, the annual lighting of the city’s Christmas tree and Hanukkah menorah at Triangle Park.
Legendary Festival of Lights brightens up the ballpark at Legends Field. Winter Village at Gatton Park features a soaring 80-foot high digital Christmas tree and a dazzling, multi-sensory display that captures the magic of the season. Southern Lights is a three-mile driving tour of twinkling displays. Christmas at Mustard Seed Hill is a spectacular holiday tradition in Millersburg, Kentucky, just 30 minutes north of Lexington. And historic Shaker Village of Pleasant Hill hosts Christmas by Candlelight tours and Illuminated Evenings events that are as educational as they are eye-pleasing.
5. Warm Up To Lexington’s Rich History
Pictured here: Ashland, The Henry Clay Estate decorated for the holidays
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. Step inside and explore rooms filled with period furniture, family portraits, and artifacts from the Todd and Lincoln families. Waveland and Shaker Village of Pleasant Hill are both gems of historic architecture that host special holiday events. And LexHistory offers a fantastic overview of the city’s most notable people, places, and happenings.
6. Feed Your Soul With Seasonal Flavors
Pictured here: Dining at Granddam at The Manchester Hotel
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 your soul with seasonal dishes and special holiday menus from eateries like Granddam at The Manchester Hotel, Holly Hill Inn, Dudley’s on Short, Italx, Corto Lima, Carson’s, Mileta, and The Obstinate Sons. Find more places to indulge this winter on our Restaurants page.
7. Have a Romantic Downtown Date Night
Pictured here: Fireplace at Elkhorn Tavern
In the wintertime, Downtown Lexington has that unmistakable holiday ambiance that can take date night to another level. Head to the heart of the city with your special someone and soak up all the romantic vibes in classy but cozy bars like Elkhorn Tavern, Ona, Harvey’s, and Georgie’s Social House. Settle into the evening at Trifecta: Glass - Art - Lounge, a hidden speakeasy surrounded by a working glassblowing studio, or grab a cocktail at Lockbox before you wander the two-story gallery of stunning contemporary art.
End the night with a moonlit stroll to Triangle Park and skate the night away at the outdoor ice rink. The holidays will be over before you know it, but the Bluegrass memories will last a lifetime.
8. Ring in the New Year
Pictured here: The Burl
Ring in the New Year in Lexington, where festive energy and a touch of sparkle set the stage for an unforgettable night out. Celebrate the European way—no passport required—at The Willow's Midnight in Paris, a lively evening of French wine, live music, and delicious bites. Get your one-way ticket to the wild, wild west and enjoy dancing, award-winning ciders, and cocktails at Wise Bird Cider's Rhinestone Cowboy event. The Soul Blues New Year's Eve event at Greyline Station features line dancing, live performances, and music from Lexington legends. Toast the night away at Belle's Black Tie & Bubbles New Year's Eve Party, or enjoy a laid-back night with friends at Mirror Twin Brewing. However you choose to celebrate, explore our calendar of events to find the perfect way to welcome the New Year in the Bluegrass.
