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Week of Events
Trail Pass Fundraiser
Bring your horse and friends and enjoy our 4.5 – mile loop in Woodford County. Beautiful acreage in a gently rolling, primarily wooded setting. This fundraiser supports our mission to provide trauma informed outdoor adventure experiences to build resilience. This $25 pass is per person per Sunday in October. Gates will be open on for…
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…
Thanksgiving Dinner to Go 2025
Our traditional menu includes roast turkey breast, old-fashioned dressing, real mashed potatoes and gravy, creamy spinach casserole from Chef Ouita’s grandmother’s recipe, cranberry relish, and Midway Bakery rolls and pumpkin pie, all packaged and ready to serve on Thanksgiving Day. Reheating instructions included! We regret that we are unable to modify dishes/meals. Each dinner is…
My Darling & Co 3rd Birthday
I can’t believe it’s been three years since we opened our doors. We couldn’t do it without you, our loyal friends and customers. Thank you for three amazing years. It is a joy to be a part of this community. Join us to celebrate with our third annual T-Shirt GIVEAWAY (with purchase and while supplies…
Sunday, October 19, 2025
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October 19, 2025 -Hocus Pocus Brunch
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October 19, 2025 -Tunes in the Vines at Equus Run Vineyards
Hocus Pocus Brunch
Oh look, another glorious morning – makes me SICK! Enjoy a specialty brunch menu and a themed cocktail (or mocktail!) to get you in the spooky spirit with Winifred, Sarah, and Mary in our Greenhouse at The Kentucky Castle. Bubble, bubble, we’re in trouble with the amount of Hocus Pocus fans out there. Costumes are…
Tunes in the Vines at Equus Run Vineyards
Join us every Sunday for Tunes in the Vines where we feature regional musical performers. Bring a chair or blanket to sit amongst the beautiful garden. Bring your friends and family---no reservation for Tunes is required. Equus Run offers a variety of wines, beer, and cocktails!!! (Have you tried our Margarita's!!! Yum!) We have food…
Monday, October 20, 2025
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October 20, 2025 -Thoroughbred Theatre Presents: Open Mic-Night w/ Reb Butler
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October 20, 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, October 21, 2025
No events on this day.
Wednesday, October 22, 2025
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October 22, 2025 -October Murder Mystery Dinner
October Murder Mystery Dinner
Enjoy a delicious dinner in the Grand Ballroom at The Kentucky Castle. But don't get too comfy, because while you eat, our Murder Mystery Theater team, "Murder & Merriment", will have you saying "whodunnit?!” One lucky guest who solves the mystery will win a gift card to The Kentucky Castle! MYSTERY SHOWS: Oct 1 (Wed):…
Thursday, October 23, 2025
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October 23, 2025 -Post-Races Rooftop Happy Hour
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October 23, 2025 -Live Music at Rolling Oven Taproom
Post-Races Rooftop Happy Hour
Join The Kentucky Castle for a Post Race Rooftop Happy Hour this October! Sips, sophistication, and the perfect way to kick off race season. This event is free and requires no ticket; however, space is limited and is on a first-come, first-serve basis. In case of inclement weather, this event will be moved to the…
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, October 24, 2025
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October 24, 2025 -Lunch and Learn Monthly Series
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October 24, 2025 -Post-Races Rooftop Happy Hour
Lunch and Learn Monthly Series
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…
Post-Races Rooftop Happy Hour
Join The Kentucky Castle for a Post Race Rooftop Happy Hour this October! Sips, sophistication, and the perfect way to kick off race season. This event is free and requires no ticket; however, space is limited and is on a first-come, first-serve basis. In case of inclement weather, this event will be moved to the…
Saturday, October 25, 2025
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October 25, 2025 -Bourbon & Brushes Plein Air Painting and Gallery Event
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October 25, 2025 -Porch Pickin at Equus Run Vineyards with Nate Jones
Bourbon & Brushes Plein Air Painting and Gallery Event
The day begins at the picturesque campus of Bluegrass Distillers, where a selection of talented local painters will capture the scenic beauty of the distillery and its surroundings on canvas. Guests can observe the artists at work as they create beautiful, one-of-a-kind pieces from 10:00 AM-1:00PM at no cost. Following the painting session, attendees are…
Porch Pickin at Equus Run Vineyards with Nate Jones
LIVE MUSIC is back on Saturdays with our Porch Pickin’ music series at Saddlestone Distillery located at Equus Run Vineyards! Whether you enjoy a late afternoon cocktail (or two!), or your favorite bottle of Equus Run wine, you will be enjoying it while listening to the tunes of various artists each week as you take…