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5 events,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…
No cost unless you purchase a raffle ticket
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! 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.
Free
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.…
$85.00
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🍷 Sangria Sunday at Wildside Winery with Trippin Roots 🎶 Join us for an unforgettable Sangria Sunday at Wildside Winery, where exceptional music and tantalizing sangria come together for the perfect weekend escape! 🎸 Live Music: Get ready for an afternoon of Americana bliss with Trippin Roots, a band of insanely talented musicians delivering a…
Free to Attends
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8 events,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. 
Join the Woodford Chamber for a monthly meeting of the official Woodford Retail Council!Meetings are held the first Monday of each month from 9-10am at the Woodford Chamber's office.Anyone whose business is affected by or is a part of the retail industry here in Woodford County is welcome to attend!Each month has a new speaker &…
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🎤 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…
Free
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! |
7 events,
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Kick off the holiday season and join us for a festive evening at our Annual Ugly Christmas Sweater Party! Wear your tackiest sweater and join us for the fun! Bring your friends and enjoy a lively evening of great food, drinks, and music with plenty of holiday spirit as we toast the start of the…
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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.
Free
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9 events,Santa's Golf Scramble at the Woodford Club. Proceeds benefit the Cops for Kids Program. This program provides Christmas gifts for underprivileged children in Woodford County. Proudly sponsored by the Versailles Police Department and Woodford County Emergency Services. This event is open to everyone. Friday December 5th 11:00 am Shotgun Start Entry Fee Per Person: $60…
$ per person60
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… 
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…
$18 – $26
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Christmas Tree Lighting in Downtown Versailles ✨🎄 Brought to you by Community Trust Bank, Woodford County Fiscal Court & the City of Versailles Kick off the holiday season in the heart of Downtown Versailles as we light our community Christmas tree! 🎶 Enjoy festive performances by Jane’s School of Dance and the Woodford County Choirs…
FREE
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12 events,
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FREE SANTA CLAUS pictures for the kiddos, families & pets (on leash), same Santa Claus at events in Midway & Versailles. You take the pictures. Shop for Christmas gifts from small, local businesses including blankets, woodcarvings, clothing, candles, picture frames, perfume, sweet treats & breads, leather goods & more.
Free Santa Claus pictures
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Celebrate the spirit of the season at Wildside Winery's Christmas Market on December 2nd from 12:00 PM to 7:00 PM and December 3rd from 12:00 PM to 5:00 PM! Join us for a delightful holiday experience filled with unique handcrafted treasures, delectable food vendors, and live music under the enchanting pavilion. Our Christmas Market is…
$10
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Start your season with a holiday open house on Saturday, December 4th in our beautifully decorated event barn. Featuring the release of our annual Holiday Blush Wine, along with music and local artists, you'll get inspired with wonderful ideas for gift giving.
Free
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8 events,
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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…
$275
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8 events,
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🎤 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…
Free
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! |
7 events,
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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. 
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! |
7 events,✨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!…
Free to Attend
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… |
7 events,
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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.
Free
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10 events,
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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!
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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!
FREE
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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…
FREE
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6 events,
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We re launching a new way to support our friends in Kentucky's craft-distilling community - and wed love for you to be part of it. Each week this winter, The Stave will spotlight one local distillery by featuring your bourbon in cocktails, sipping pours, and special food pairings-all week long. Then on Sunday from Noon-3PM,… |
7 events,
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🎤 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…
Free
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! |
6 events,
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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.
Free
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6 events,
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🎤 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…
Free
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! |
5 events,
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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.
Free
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5 events,
The Woodford Chamber's monthly Lunch & Learns are on the 4th Friday of each month from 12-1pm with locations varying month to month.This series highlights one Woodford County business each month & provides insight to the business ecosystem in Woodford County while enjoying a delicious complimentary meal at a local restaurant. Go to the Chamber community… |
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5 events,Free, family-friendly Plant Party hosted by community members at the Rolling Oven Taproom from 1-3pm the last Sunday of every month, year-round. Bring your houseplants, cuttings, vegetable plants, flowers, or plant related items to sell, swap or share. Questions, text Lauren Perkins at 859-333-2380
FREE
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6 events,
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🎤 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…
Free
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! |
4 events,New Year’s Eve Party!! 🎉 Open to the public! Party starts at 9 with party favors and champagne toast. $5.00 COVER
$5
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4 events,
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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.
Free
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3 events,
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Grey Ridge Farm 1345 Scotts Ferry Road East Versailles, KY 40383 Julie Kaufman 859-753-8125 Camp open to children 6 & up No riding experience necessary Heated barn/indoor arena Riding Arts & Crafts Horse activities
$150
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