Top Things to Do This Fall in Woodford County, Kentucky

Fall in Woodford County is pure magic. The crisp air, golden leaves, and rolling bluegrass hills create the perfect backdrop for festivals, food, and family fun. Whether you’re looking for small-town charm, outdoor adventure, or festive celebrations, Woodford County has it all.

Here’s your ultimate guide to the top fall experiences you don’t want to miss.

Fall Festivals & Community Events

Woodford County comes alive in autumn with some of the region’s most loved festivals:

• Midway Fall Festival – September 20–21
• Millville Days Festival – September 13
• Nights on Main – September 11 & October 9 (Downtown Midway & Versailles stay open late, 5–8 pm)
• Oktoberfest at Highbramble Park – October 10–11
• Woodford Spooktacular – Thriller dancing in the streets, Trunk-or-Treat, costume contests, and so much more!

Seasonal Experiences You’ll Love

• Bluegrass Railroad Museum – All aboard for scenic Fall Train Rides through Kentucky’s countryside.
• Rail Explorers – Pedal-powered rail cars let you take in the fall colors on a one-of-a-kind adventure.
• Eckert’s Orchard – Apple picking, pumpkin patches, cider donuts, and family-friendly fall fun.

Sip, Savor & Celebrate at Wildside Winery

Wildside Winery is hosting a lineup of can’t-miss fall festivals:

• Balloon Festival
• Harvest Festival
• Pumpkin Festival
• Witches & Wine Festival

Pair local wine with live entertainment and the magic of the season.

A Touch of Mystery at The Kentucky Castle

Step into a fairytale this fall at The Kentucky Castle, featuring:

• Hocus Pocus Brunch – A whimsical, seasonal twist for the whole family.
• Murder Mystery Dinners – An interactive evening of intrigue inside the iconic castle.

Plan Ahead: Thanksgiving in Woodford

Don’t wait until the last minute—book your Thanksgiving dinner reservations early at your favorite Woodford County restaurants. Local chefs are ready to bring you a farm-to-table holiday experience you’ll remember.

Plan Your Visit

Make the most of your fall with the Visit Woodford App—your go-to guide for events, dining, and attractions in the heart of Horse & Bourbon Country.

Explore the full calendar and follow @VisitWoodford on social for updates and inspiration.

This season, discover why Woodford County is the top fall destination in Central Kentucky!