Home Arts Lexington’s Ultimate Holiday Guide 2023

Lexington’s Ultimate Holiday Guide 2023

Even if you’ve been running into Santa in the Target aisles since Labor Day, the holiday season doesn’t officially begin until Halloween is safely behind us. 

Holidays in the Bluegrass have something for everyone, from parades to plays, and concerts to 5Ks. You can dress like a reindeer and run a half marathon if you’re so inclined. 

As always, confirm dates and times with the venue. 


NOV 4 Lex Glow Ride, Brighton Trail 

NOV 9 Candlelight Tradition, Frankfort

NOV 25 Southern Lights, Kentucky Horse Park  

NOV 26 Lexington Tree Lighting 

DEC 1 Christmas at Mustard Seed Hill

DEC 2 A Kentucky Christmas at Ashland 


Kick off the Holiday Season of Lights with Lexington’s annual Glow Ride. Light up your bikes, skates, scooters and skateboards and take them out for a spin! Lex Glow Ride is a family-friendly event for riders of all ages and experience levels to learn about bike and alternative transportation safety. There will be several safety stations, including a tire check, helmet decorating and reflective gear giveaway. Youth and adult bikes will be available to check out on a first-come, first-served basis. Saturday, November 4. The festival begins at 5 p.m. The ride starts at 7 p.m. Brighton Trail, behind 1750 Bryant Road.

Guests for the long holiday weekend? Enjoy Thanksgiving weekend with Southern Lights at the Kentucky Horse Park, a three-mile driving tour of lights. Celebrating its 30th year at the Kentucky Horse Park, Southern Lights invites guests to view over a million twinkling lights on a drive-thru tour.  Enjoy the return of the Holiday Village which features photos with Santa, Animal Land, model trains, and so much more. 5:30 pm to 10 pm thru December 31. (Closed on Christmas Day.) Named one of Kentucky’s Top 10 Winter/Holiday Festivals and Events by Kentucky Travel and Tourism.


Head to Triangle Park on November 26 for Lexington’s Annual Holiday Lighting Festival. Lexington’s Christmas Tree will be lit with beautiful bright lights, and Lexington’s Hanukkah Menorah will shine ahead of the festival. Plus, community choirs will sing festive songs which are sure to put everyone in the holiday spirit! Santa will visit at 6 pm to light the tree, followed by Christmas carols with The Lexington Singers.


Ashland Illumination at the Henry Clay Estate begins at 5:30 pm on Saturday Dec 2 with the First Candlelight Tour 5:30 – 7 pm. Additional candlelight tours are scheduled for Thursday Dec. 7, and Saturday Dec. 9.


Holiday Music


NOV 21 Chris Isaak: It’s Almost Christmas Tour, The Kentucky Center, Louisville

NOV 26 Lexington Chamber Chorale, 2nd Presbyterian 

DEC 1 An Oak Ridge Boys Christmas, Renfro Valley

DEC 2 Celtic Women Christmas Tour, Norton Center (Danville)

DEC 10 Alltech’s Celebration of Song, KY Horse Park 

DEC 14 Preservation Hall Jazz Band’s Creole Christmas, The Kentucky Center 

DEC 15 Christmas with the Beatles, The Kentucky Center 



DEC 2 Lawrenceburg Christmas Parade

DEC 2 St. “Nich” Christmas Festival, Nicholasville 

DEC 2 Lexington Christmas Parade 

DEC 9 Danville Christmas Parade 



NOV 11 Junior League Holly Day Market, Lexington Center

NOV 18 Holiday Market, The Kentucky Castle 

NOV 18 Bluegrass Creative Market, The Summit 

DEC 2 Christmas Market, Ashland Henry Clay Estate 


Ashland, the Henry Clay Estate hosts their Annual Christmas Market, Noon to 5:30 pm on Saturday Dec 2. Santa Selfies 3 pm – 5:00 pm Kentuckians Chorus 5 pm – 5:30 pm Ashland Illumination 5:30 pm First Candlelight Tour 5:30 – 7 pm, last entry at 7  pm (Additional candlelight tours on Thursday Dec. 7, and Saturday Dec. 9)


Run For It

NOV 18 Southern Lights Stroll, KY Horse Park 

NOV 18 Turkey Strut 5k, Nicholasville 

NOV 18 Turkey Trot Fun Run, Versailles

NOV 19 Gobbler Half Marathon, Lexington

DEC 2 Santa Shuffle 5k, Versailles 

DEC 3 Frosty 5k, Frankfort

DEC 8 St. Nich Ugly Sweater 3k, Nicholasville

DEC 9 Reindeer Ramble, Keeneland

DEC 9 St. Nicholasville Ugly Sweater 5k, Nicholasville

DEC 16 Frosty Feet Winter Mileage Challenge, Lexington

JAN 1 Frozen Rails 5k + 10k, Midway


Stage & Theatre 


NOV 18 Irving Berlin’s White Christmas, Lexington Opera House

NOV 21 A Christmas Story, Lexington Opera House 

NOV 21 The Best Christmas Pageant Ever, Lexington Children’s Theatre 


The Bradley family’s church Christmas Pageant is always the same, year after year – until the Herdmans show up. Join the Lexington Children’s Theatre for The Best Christmas Pageant Ever, Nov 21 hrough Dec 4, 2023. 



NOV 5 Lexington Ballet presents a pop-up Nutcracker performance, Lexington Public Library 

NOV 21 Nutcracker! Magical Christmas Ballet, UK Singletary Center

DEC 8 The Brown-Forman Nutcracker, The Kentucky Center 

DEC 9 Kentucky Ballet Theatre presents The Nutcracker, Lexington Opera House

DEC 22 The Nutcracker, EKU (Richmond)

This article appears on pages 9-11 of the November 2023 issue of Ace. To subscribe to digital delivery each month, click here.