Join us at Rolling Oven Taproom every Sunday for your favorite brunch cocktails, flat breads, pizzas, and more!

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…

🎤 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…

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!

Money Mindset Monthly, a series designed  by the Woodford Chamber and Thrivent Financial to empower people of all ages with the knowledge and confidence to take control of their financial wellness!Managing your finances can feel overwhelming, but breaking it down into achievable steps makes all the difference. Whether you're saving for a dream purchase, tackling debt,…

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.

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…

Tacos N’ Tequila – The Ultimate Taco & Tequila Experience! Get ready for a party like no other! Tacos N’ Tequila is Lexington’s most exciting annual event, bringing together the city’s top restaurants to put their unique spin on the beloved taco. Indulge in mouthwatering tacos, sip on handcrafted tequila cocktails, and enjoy lively music…

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…

Join Woodford Humane Society at world-famous Coolmore's Ashford Stud for the 5th running of the Triple Crown Trot 5K! The Trot is a chip-timed road race that runs on a private course entirely inside of Ashford Stud. Run or walk the same paths as Triple Crown champions American Pharoah and Justify! Registration is open now…

Join us for Market Days at The District, a vibrant community event celebrating local flavors, creativity, and fun for all ages! Shop a wide variety of farm-fresh produce and locally made products, perfect for stocking your kitchen with seasonal goodness. Enjoy grab-and-go food and drink options from your favorite local vendors while soaking in the…

Paint delicate 5×7 florals in this calming, beginner-friendly class—open to all experience levels. You’ll learn the basics of brushwork, color mixing, and composition as you create your own floral study to take home. All supplies provided — brush, paper, palette, paints, and more Optional: Add a display-ready frame at checkout (+$10) Midway Art Studios Saturday,…

Join historian Mack Cox the hear the story of the marriages, mentorship and geography that entwined the lives of two of Kentucky’s most important artists, Matthew Harris Jouett (1788-1827) and Oliver Frazer (1808-1864), and their descendants. This talk will tell that story and the travels and adventures of these paintings as they moved from the…

The Midway Business Association proudly presents the Midway Summer Block Party series on E. Main Street from 6-10pm on Saturday May 24. This is a free family-friendly event! ▪️6-10pm Local vendors; arts and crafts, food, community organizations, beer and wine. *Select Shops open late *Restaurants ready to serve you 🎵 7-10pm Bring your own lawn…