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Week of Events
Festival Of Trees
Woodford County Festival Of Trees is celebrating its 8th season. There are 20+ Trees & More donated by local businesses that are located throughout the county. This is a great opportunity to take a roadtrip with family and friends to see different decorated trees and the holiday decorations while visiting local businesses. If you find…
Holly Hill Restaurant Group Gift Card Campaign
This holiday season, when you buy $100 in gift cards for your friends and clients, Holly Hill will give you a bonus $20 gift card to use at any of our locations. It's our way of saying "thank you" for letting us help you share the magic of local food!
Tunes in the Barn at Equus Run Vineyards
Back by popular demand we are extending our Tunes in the Vines to Tunes in the Barn on Sundays. We have local bands playing and we will be covered by the barn patio and space heaters for warmth! Can't wait to see you there.
Murder Mystery Dinner at Equus Run Vineyards
November 21st: The Murdered Mistress December 12th: 'Twas the Murder Before Christmas January 23rd: The Ghost of Windsor Manor February 13th: Murder at the Bunnytail Mansion March 6th: Henry Potter and Princess of Prophecy Enjoy a "murderous" good time as you dine on a lovely chef inspired dinner while gaining clues to solve the mystery.…
Holiday lunches at Holly Hill Inn
Join us for our annual Holiday Lunches at Holly Hill Inn! Days are now live on Open Table for reservations - Monday-Friday beginning December 1 and continuing through December 30.
Woodford’s OLD FASHIONED WEEKEND
Did you think we were talking about classic, whimsical Christmas? Why, yes- we are! But this is from the Birthplace of Bourbon so local businesses are whipping up their favorite OLD FASHIONEDs just for you! Win an etched Bourbon Glass, too! Here's the information!Did you think we were talking about classic, whimsical Christmas? Why, yes- we are! But this…
WOODFORD THEATRE PRESENTS: “ANNIE”
December 5-7 / 12-14 / 19-21, 2025 Fridays & Saturdays at 7:30pm Sundays 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…
🌿 Wild Woman Book Club at Wildside Winery – December ❄️
✨Wild Woman Book Club at Wildside Winery 📅Wednesday, December 10th, 2025 ⏰6:30 PM 📍Wildside Winery | 5500 Troy Pike, Versailles, KY 💻RSVP at wildsidewinery.com Wild women, wine lovers, and bookworms — our circle is growing, and you’re invited. This month’s read is TBA -- stay tuned to our website and social media accounts for updates!…
Sunday, December 7, 2025
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December 7, 2025 -Woodford Reserve Holiday Brunch
Woodford Reserve Holiday Brunch
Ignite your holiday spirit! Join us for an unforgettable Holiday Brunch event. Your journey begins with a guided exploration of our historic distillery, followed by a cocktail flight and fully catered family-style brunch, perfectly crafted for the festive season. One of our legendary Master Distillers, Elizabeth McCall or Chris Morris will join you for brunch…
Monday, December 8, 2025
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December 8, 2025 -Thoroughbred Theatre Presents: Open Mic-Night w/ Reb Butler
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December 8, 2025 -QuizMania Trivia
Thoroughbred Theatre Presents: Open Mic-Night w/ Reb Butler
🎤 Calling All Talented Souls! 🎸 And their friends! Join us every Monday night for a music-filled extravaganza at the Thoroughbred Theatre & Wine Bar's Open Mic Night with the incredibly talented Reb Butler! 🍷🎶 🎙️ Whether you're a seasoned performer or just looking to share your musical passion with a friendly crowd, our stage…
QuizMania Trivia
TRIVIA IS BACK with QuizaMania Mondays! LiveWire Entertainment brings us a brand new Trivia Night experience at The Woodford Club. You’ll get everything from general trivia to Name That Tune, game show style challenges and more! Join us Mondays in raising the bar for the live trivia experience!
Tuesday, December 9, 2025
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December 9, 2025 -Commonwealth Credit Union Power Checking
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December 9, 2025 -Chamber Coffee at the Library
Commonwealth Credit Union Power Checking
Power Checking is an all-in-one checking account that powers your spending and with built in high-yield savings, grows your balance at the same time. Our new Power Checking Account does so much more, all with no minimums, no limits-only unparalleled benefits.
Chamber Coffee at the Library
Join us for our monthly discussions featuring guest speakers from various organizations in the community. Come and have a cup of coffee on us, learn something new, and engage with like minded individuals in your community!
Wednesday, December 10, 2025
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December 10, 2025 -Women of Woodford Monthly Series
Women of Woodford Monthly Series
Join the Woodford Chamber''s Women of Woodford group for a monthly meetup! Meetings are every second Wednesday of the month from 8:30-9:30am! Each meeting location and speaker topic highlights an amazing business woman or group of women working to make Woodford County a better place to live and work! Brought to you by our sponsors at…
Thursday, December 11, 2025
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December 11, 2025 -Live Music at Rolling Oven Taproom
Live Music at Rolling Oven Taproom
Mash Grass performs Bluegrass music every Thursday night starting at 6PM. Join in on the fun this Thursday as we soak up the sun on the patio and watch it set as we finish up the night.
Friday, December 12, 2025
No events on this day.
Saturday, December 13, 2025
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December 13, 2025 -Save the date for the Santa Shuffle 5k and Kid’s Dash
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December 13, 2025 -Winter Art Market
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December 13, 2025 -A Wonderful Woodford Christmas
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December 13, 2025 -🎈✨ Winter Balloon Glow at Wildside Winery
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December 13, 2025 -Living Windows
Save the date for the Santa Shuffle 5k and Kid’s Dash
Run through a downtown that is lit up and decked out with holiday decor to support local businesses through the Woodford County Chamber of Commerce with this annual 5K! Bring the whole family as kids of any age have the opportunity to participate in the Kids Reindeer Dash race around the courthouse!
Winter Art Market
Visit our Studio Gallery where you'll find unique exclusive gifts for the Season! We'll be waiting on you with our Mulled Cider & Coffee Bar... See you in Midway!
A Wonderful Woodford Christmas
A Wonderful Woodford Christmas ✨🎄 Brought to you by Community Trust Bank, Woodford County Fiscal Court & the City of Versailles, Kentucky 📅 Saturday, December 13th 🕛 12PM – 5PM 📍 The District, 105 Rose Hill Ave, Versailles Celebrate the magic of the season at A Wonderful Woodford Christmas! ❄️⛸️ Enjoy a festive afternoon filled…
🎈✨ Winter Balloon Glow at Wildside Winery
🎈✨ Winter Balloon Glow at Wildside Winery 📅 Saturday, December 13 | 4:00–7:00 PM 🌅 The glow begins at sunset (~5:00 PM) 📍 Wildside Winery | 5500 Troy Pike, Versailles, KY 🎶 Live Music: TBA 🎟 Free Admission | Wine and food available for purchase Bundle up, sip your favorite Wildside wine, and watch the…
Living Windows
Join us downtown from 5-7 and enjoy our “Living Window” display up and down Main Street.