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As the crisp autumn air settles in and the leaves begin to change, Woodford County comes alive with seasonal charm and endless opportunities for fun. From apple orchards and bourbon tours to festivals, theatre, and train rides, there’s something for everyone to enjoy this fall. Here are the top things to do in Woodford County this season.
Eckert’s Orchard
A fall favorite for families, Eckert’s Orchard offers more than just apple picking. Visitors can enjoy the ultimate playground, shop in the country store, or cheer on pig races. Seasonal treats like warm cider donuts make the experience even sweeter.
Woodford Theatre
The Woodford Theatre kicks off its fall season with a new lineup and season ticket sales. Known as one of the best community theatres in the region, it’s the perfect place to enjoy a night of live entertainment.
Shop Local
Fall is the perfect time to support local businesses. From fresh mums and pumpkins to seasonal décor and apparel, shopping local adds a festive touch to the season. And don’t forget to download Woodford Wallet app, which will send a push notification when the matching program returns, offering a $5,000 match from Woodford County Tourism. Families can receive a 100% match on gift card purchases up to $100 while supplies last.
Markets & Festivals
Woodford County is brimming with fall festivals and markets. Highlights include Oktoberfest at Highbramble Park on October 10–11 and weekly farmer’s markets. A full list of events can be found at VisitWoodford.com/Events.
Fall Favorites on the Menu
Local restaurants and The Amsden are rolling out seasonal specials, from pumpkin spice lattes to hearty fall dishes. A dining passport is available to guide visitors to the best flavors of the season.
A Gilmore Girls Weekend in Stars Hollow
Experience the cozy, whimsical magic of Stars Hollow in Versailles! On October 11 and 12, enjoy music flowing throughout the streets and outdoor screenings of classic Gilmore Girls episodes. Join book club, make some crafts and take part in some family-friendly activities. Bring your friends, your family, and your love to Luke’s Diner themed fun – grab a coffee, but no cell phones allowed. (Lorelai never followed that rule, so why should you?) With fall-inspired photo ops, shopping, unique vendors and artisan booths, it will be a charming weekend. Brought to you by the shops and merchants of Downtown Versailles.
Woodford Spooktacular – Halloween Festivities
Halloween in Woodford County is packed with family-friendly fun.
- October 18: Midway Thriller 5K – Zombies take over the streets of Midway at this inaugural 5k. Enjoy a post-race block party with live music, food and drinks.
- October 26: Woodford’s Spooktacular – Thriller Parade, Trunk or Treat, costume contests, pumpkin decorating, Touch a Truck, and more (4–8 p.m.).
- October 31: Official Trick-or-Treating from 6–8 p.m.
Thanksgiving Reservations
It’s never too early to plan for Thanksgiving. Local restaurants offer reservations for holiday meals, while bakeries and shops provide desserts and host gifts. Visitors can also plan itineraries for family and friends traveling in for the holiday at VisitWoodford.com.
Bourbon & Horses
Fall is one of the best times to experience the Bluegrass. Visitors can book a horse farm tour through Horse Country or enjoy bourbon tastings at local distilleries, Bluegrass Distillers, Woodford Reserve and Castle & Key, as well as bourbon bars. With bourbon shops and year-round horse events, it’s a quintessential Woodford County experience.
Train Rides
Scenic train rides are a must-do in the fall. Rail Explorers offers pedal-powered rail cars for a unique way to take in the autumn colors. Families can also ride the Pumpkin Train with Bluegrass Railroad, tour the train museum at The Depot, or dine along Midway’s historic downtown railroad at Ricardo’s, a former train station.
Wildside Winery Events
Wildside Winery hosts a variety of seasonal events, including:
- Harvest Market – October 4
- Pumpkin Festival – October 11–12
- Witches & Wine – October 25
The Kentucky Castle
The iconic Kentucky Castle offers a magical lineup of fall events. Families can enjoy the whimsical Hocus Pocus Brunch, while adults can take part in Murder Mystery Dinners throughout September and October. Rooftop Keeneland After Parties add a lively twist to the season.
Woodford County is the perfect destination for fall adventures. Whether it’s savoring seasonal flavors, exploring local festivals, or enjoying bourbon and horse country, the county offers a rich blend of tradition and excitement. This autumn, make memories in the heart of the Bluegrass with experiences that capture the true spirit of the season.
