Lucky you. You just found LEXtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout the Horse Capital of the World each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Seasonal
Christmas Shoppe in the Keeper’s Cottage | Now-Saturday, Dec. 6 | 10 a.m. | Ashland - The Henry Clay Estate | Price of purchase | Get a head start on your holiday shopping with artwork from local makers during the “A Kentucky Christmas” at Ashland celebration.
The Woodland Triangle Holiday Shop Hop | Saturday, Dec. 6-Sunday, Dec. 7 | 10 a.m.-6 p.m. | The Woodland Triangle | Free | This neighborhood shopping trip offers a fun way to sip, shop, and explore a dozen local businesses. Pick out holiday gifts, enjoy seasonal discounts and treats, and earn raffle entries as you visit each spot.
Holiday Market - Lavender In Bloom | Saturday, Dec. 6 | Times vary | Lavender In Bloom, Georgetown | Price of purchase | Join Lavender In Bloom for its first-ever Holiday Market, featuring handmade favorites, new artisan collaborations, ornament painting and candle-making workshops, a customizable bath salt bar, and chances to win free product giveaways.
Downtown Lexington’s Holiday Parade | Saturday, Dec. 6 | 11 a.m. | Downtown Lexington | Free | Santa and a lineup of local holiday floats will make their way down Main Street for this annual community tradition. Applications to be part of the parade are available and due Wednesday, Dec. 3.
“A Kentucky Christmas” Ashland Illumination | Saturday, Dec. 6 | 4-6 p.m. | Ashland - The Henry Clay Estate | Free | Kick off the holiday season at one of Lexington’s favorite traditions with the lighting of Ashland, the Henry Clay Estate’s Christmas tree.
For the fam
Winter Village at Gatton Park | Thursday, Dec. 4-Tuesday, Dec. 23 | 5-10 p.m. | Gatton Park | Free | Gatton Park will transform into Winter Village from Dec. 4–23, featuring an 80-foot Christmas tree, hundreds of thousands of holiday lights, private igloos, cozy gathering spots with fire pits, seasonal treats, and more.
Once Upon A Holly Day: Princess Celebration | Saturday, Dec. 6 | 12-1:30 p.m. | Alltech Arena | $45 | Bring your little princes and princesses to the Holly Day Market for photos with Tiana, Belle, and Elsa, plus story time and a magical dance party.
Breakfast with the Grinch | Sunday, Dec. 7 | 9 a.m. | Joseph-Beth Booksellers | $20 | Enjoy a breakfast of pancakes, sausage, fruit, and a choice of coffee, tea, milk, or orange juice with the Grinch at the at Bronte Bistro.
Music + comedy
“Rudolph the Red Nosed Reindeer, Jr.” | Saturday, Dec. 6-Sunday, Dec. 7 | Times vary | Lexington Opera House | $22+ | “Rudolph the Red-Nosed Reindeer” comes to life in this 60-minute musical. Follow Rudolph and his misfit friends on a heartwarming journey to save Christmas. Perfect for all ages.
Slay Bells 2025 - A Holiday Drag & Variety Show Spectacular | Sunday, Dec. 7 | 5-10 p.m. | Lyric Theatre and Culture Center | $40 | Enjoy celebrity guest stars Andrew Shayde, Silas House, and Terry Mullins for a performance benefitting Moveable Feast Lexington.
Trans-Siberian Orchestra - The Ghosts Of Christmas Eve | Wednesday, Dec. 10 | 7 p.m. | Rupp Arena | $80+ | A high-energy rock opera bringing holiday classics and dazzling visuals to life.
Get social
Book Swap | Saturday, Dec. 6 | 12-4 p.m. | Blue Stallion Brewing Company | Free | Swap your well-loved books for new reads at this free community book swap. Bring up to 5 books in good condition — kids’ books are welcome, and adult titles can be wrapped with a note.
Gingerbread House Decorating | Thursday, Dec. 11 | 6 p.m. | 100 East Main St 2nd Floor, Midway | $100 | Celebrate the season in Midway with a cozy gingerbread-house workshop, complete with a hot chocolate bar and light bites for guests 14 and up.
Holiday Ho Ho Ho-Down | Saturday, Dec. 13-Sunday, Dec. 14 | 12-4 p.m. | Wise Bird Cider Co. | Free | Celebrate the season at Wise Bird Cider’s Holiday Ho Ho Ho-Down. This free, family-friendly event features ornament decorating, local vendors, tasty eats, and photos with Santa.
Holiday Group Run/Walk | Thursday, Dec. 18 | 6 p.m. | John’s Run/Walk Shop | Free | Wear your tackiest sweater, and snap a group photo by the Triangle Park Christmas Tree at 6:30.
Classes
Holiday Basketmaking Workshop | Saturday, Dec. 6 | 9 a.m.-12 p.m. | The Arboretum State Botanical Garden of Kentucky | $40 | Head to the Arboretum for an interactive basket-making session with local maker Teresa Arnold.
Royal Icing Cookie Class at the Holly Day Market | Sunday, Dec. 7 | 11:30 a.m.-1 p.m. | Alltech Arena | $45 | Calling all holiday bakers. Join a 90-minute Royal Icing Cookie Decorating Class at the Holly Day Market, led by Sweet and Sassy Ashley’s LLC. All supplies are provided, and tickets include market entry and parking.
Holiday Focaccia Class | Sunday, Dec. 7 | 1-2:30 p.m. | Harkness Edwards Vineyards, Winchester | $48 | Create your own edible artwork in this focaccia bread class. Learn expert techniques, take your piece home to bake, and enjoy a complimentary glass of wine.
Holiday Mini Pie Decorating Class | Sunday, Dec. 7 | 3:30-5 p.m. | Harkness Edwards Vineyards, Winchester | $48 | Learn the art of mini pies in this hands-on class. Make and decorate a dozen pies with step-by-step guidance, take them home to bake, and enjoy a glass of wine.
Holiday Wreath-Making Class | Saturday, Dec. 13 | 10 a.m.-12 p.m. | The Arboretum State Botanical Garden of Kentucky | $25 | Make a seasonal wreath in this hands-on workshop. Follow step-by-step guidance and leave with a beautiful wreath to display at home.
Candle Making Experience with Wick & Mortar at Lane’s End Farm | Saturday, Dec. 13 | Times vary | Lane’s End Farm, Versailles | $60 | Tour Lane’s End Farm’s champion stallions and create your own eight ounce custom candle with premium ingredients. Light refreshments included.
Santa’s Cookie Decorating Class | Saturday, Dec. 13, Sunday, Dec. 21 | Times vary | Harkness Edwards Vineyards, Winchester | $48
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.