Dec 06 Saturday
The 2025 edition of Woodford County Festival of Trees is a trail of decorated Christmas Trees and other holiday related items located throughout the county that the community can purchase raffle tickets to win. This is our 8th Annual event. This year there are 20+ Trees & More donated by local businesses and community members. This is a great opportunity to take family and friends out for a day trip while supporting local businesses and youth in our community. Proceeds support local youth via Shop With A Cop and Young Life.
The Junior League of Lexington’s 19th Annual Holly Day Market will take place from December 5-7 at Alltech Arena. This popular event gathers vendors from across the country, offering shoppers a convenient, one-stop destination for holiday gifts. From jewelry and clothing for all ages to toys, books, holiday decorations, ornaments, art, gourmet food, and more, the market has something for everyone. And, thanks to generous sponsors, parking is free all weekend long!In addition to the shopping experience, attendees can enjoy Daily Events, participate in a silent auction, and even visit Santa and Mrs. Claus to kick off the holiday season. Proceeds from the event benefit the Junior League of Lexington and the local nonprofits it supports.
Event Hours:• Holly Day Eve Kickoff: Friday, December 5, from 5-9 p.m.• Saturday, December 6: 10 a.m.-6 p.m.• Sunday, December 7: 11 a.m.-5 p.m.
Tickets:• Holly Day Eve: $25• General admission: $15• Children 10 and under: Free• Parking is free for all shoppers
Learn more at www.HollyDayMarket.com.
Based on the animated television special “Rudolph the Red Nosed Reindeer” adapted from the story by Robert L. May and the song by Johnny Marks.
Developed by Character Arts Creations, LLC
The holiday classic soars off the screen in this Broadway Junior, 60-minute musical adaptation of the beloved television special. Because of his shiny nose, Rudolph doesn’t feel like he belongs in Christmastown and sets off to find a place that accepts him. Along his journey, he encounters fellow misfits, only to realize that home is where he has belonged the whole time. When a storm threatens to keep Santa’s sleigh from taking flight, it’s up to Rudolph to save Christmas.
Perfect for all ages – grab your tickets now and light up your holiday season!
Kids- $22 Adults- $27
Sun, Nov 30 – 2:00 pm
Sat, Dec 6 – 2:00 pm & 7:00 pm (PWYW)
Sun, Dec 7 – 2:00 pm
*Pay What You Will Sat, Dec 6th @ 7pm
Thursday, December 4 – Tuesday, December 23, 2025 5:00 pm–10:00 pm Nightly | FREE
There’s no place like home for the holidays—Winter Village at Gatton Park brings Lexington together to celebrate the season.
Step inside the park’s soaring 80-foot high digital Christmas tree and be surrounded by a dazzling, multi-sensory display that captures the magic of the season. Wander beneath hundreds of thousands of warm, twinkling lights and explore festive games and crafts, or immerse yourself in the glowing winter playground, where whimsical lights, interactive surprises, and playful details spark laughter, imagination, and holiday joy at every turn.
Savor the season with warm cocoa, handcrafted cocktails, and delicious holiday treats as the sights, sounds, and flavors of the holidays come alive.
A Wonderful Woodford Christmas Parade 2025 ✨🎅📍 Downtown Versailles – Main Street📅 Saturday, December 6th🕔 Parade begins at 5:00 PMCelebrate the magic of the season as Main Street comes alive with lights, music, and holiday cheer! Our annual Christmas Parade features our City and County first responders, local departments, a special performance by the Kentucky State University Marching Band & much more!Bring the whole family and enjoy this beloved community tradition as we welcome the holidays in style.Interested in being part of the parade?👉 Sign up here: https://tinyurl.com/msa4ten
Join Lexington Children’s Theatre and the Lexington Fraternal Order of Firefighters for a holiday celebration full of joy and giving! Before the Pay What You Will performance of Rudolph the Red-Nosed Reindeer, bring a toy to donate, explore a real fire truck, and meet Santa outside the Opera House.
Learn more about all accepted gifts and all toy drop locations and events at https://lfdfof.org/toy-program/.
FREE EVENT! Event Time: December 6, 2025 – 6:00 pm-6:45 pm Event Location: Lexington Opera House
Discover More Series supported by the PNC Foundation.
On a cold night in a drafty farmhouse, Carolyn goes into labor just as her parents are arriving for Thanksgiving dinner. She can't tell her father, an obstetrician, that she is having a home birth. She must pretend that everything is normal, including passing off the midwife as the vet! When family feuding begins over where this baby should be born, tensions rise and do does the laughter. A light comedy with serious intentions shows us how the human heart sometimes takes the long way home.
December 5-7 / 12-14 / 19-21, 2025Fridays & Saturdays at 7:30pmSundays at 2:00pm
Based on the popular comic strip by Harold Gray, Annie has become a worldwide phenomenon and was the winner of seven Tony Awards, including Best Musical. The beloved book and score by Tony Award winners, Thomas Meehan, Charles Strouse and Martin Charnin, features some of the greatest musical theatre hits ever written, including "Tomorrow."
With equal measures of pluck and positivity, little orphan Annie charms everyone's hearts despite a next-to-nothing start in 1930s New York City. She is determined to find the parents who abandoned her years ago on the doorstep of a New York City Orphanage that is run by the cruel, embittered Miss Hannigan. With the help of the other girls in the Orphanage, Annie escapes to the wondrous world of NYC. In adventure after fun-filled adventure, Annie foils Miss Hannigan's evil machinations... and even befriends President Franklin Delano Roosevelt! She finds a new home and family in billionaire, Oliver Warbucks, his personal secretary, Grace Farrell, and a lovable mutt named Sandy.
Dec 07 Sunday
The Junior League of Lexington’s 19th Annual Holly Day Market will take place from December 5-7 at Alltech Arena. This popular event gathers vendors from across the country, offering shoppers a convenient, one-stop destination for holiday gifts. From jewelry and clothing for all ages to toys, books, holiday decorations, ornaments, art, gourmet food, and more, the market has something for everyone. And, thanks to generous sponsors, parking is free all weekend long!In addition to the shopping experience, attendees can enjoy Daily Events, participate in a silent auction, and even visit Santa and Mrs. Claus to kick off the holiday season. Proceeds from the event benefit the Junior League of Lexington and the local nonprofits it supports.Event Hours:• Holly Day Eve Kickoff: Friday, December 5, from 5-9 p.m.• Saturday, December 6: 10 a.m.-6 p.m.• Sunday, December 7: 11 a.m.-5 p.m.Tickets:• Holly Day Eve: $25• General admission: $15• Children 10 and under: Free• Parking is free for all shoppersLearn more at www.HollyDayMarket.com.
Join the Lexington Community Orchestra for Classical Music Dances – a joyful celebration of rhythm and movement featuring music from Spain, Hungary, Russia, Austria, and Mexico. The concert begins at 3:00 PM on Sunday, December 7, 2025, at Bryan Station High School Auditorium. Admission is free, with donations appreciated. www.lexingtoncommunityorchestra.org
Dec 08 Monday
Dec 09 Tuesday
Dec 10 Wednesday
Dec 11 Thursday
Dec 12 Friday
LexPhil and The Lexington Singers return to the beautiful Cathedral of Christ the King for this holiday tradition of timeless orchestral and choral works. This awe-inspiring musical experience in a divine setting will transport all to a place of peace that evokes the spirit of the holiday season.
Buy your tickets now at lexphil.org/cathedral-christmas.
Dec 13 Saturday
Get your last-minute holiday shopping done with us at International Book Project's 4th annual Sip & Shop Holiday Market! This year's market will feature handcrafted products from a dozen local artisans, delicious food, bestselling books, and beer from West 6th Brewing!
Stop by on December 13 between 12pm-4pm to browse our wares, sip on a beer, or relax with a new-to-you book. If you find something perfect for a special person in your life, we will happily wrap it up for you at our donation-based gift-wrapping station!
You'll be shopping for a great cause, too: 50% of profits from West 6th's beer sales and all of the proceeds from bookstore sales will directly support IBP's mission of promoting literacy worldwide.
Sip & Shop is proudly sponsored by West 6th Brewing and North Lexington Living.