Kentucky Thanksgiving: The Best Fall Festivals in Lexington

From the bourbon hall of fame to caterpillar racing, a Kentucky Thanksgiving offers something truly special in the fall.

With the vibrant autumn leaves as your backdrop, there’s no shortage of exciting fall festivals in Kentucky. Whether you’re celebrating German heritage or soaking in the soulful sounds of authentic bluegrass music, there’s an event for every taste.

To help you plan your season, we’ve highlighted some of the best fall events to complement a Kentucky Thanksgiving. No matter which one you choose, you’re guaranteed a great time—and with reliable transportation, getting there is stress-free.

1.Taste of Louisville Festival – Louisville, KY

Louisville is a great city for foodies and this festival is perfect for you if you count yourself among them.

Located at the historic and famous Churchill Downs, the Taste of Louisville is about to host their 45th annual event and promises delicious food and refreshing drinks.

Feel good while feasting. Portions of admission fees will go to several charities, so you can give back while enjoying what Louisville has to offer.

Over 50 local restaurants will be offering samples included in your ticket price.

2.Scarefest – Lexington, KY

For those that look forward to the spookiest fall holiday, this KY fall festival is sure to please.

A film festival for movie lovers is just one of the fun events going on at the annual event. Photo-ops with celebrities and character performers as well as live music make Scarefest a party atmosphere that attracts convention-goers as well as people who just want to celebrate the fall.

Join a paranormal investigation with real experts and grab a bite at one of the many food trucks in attendance.

You can even grab your friends and try to win the costume contest. With this being a great event for large groups, you may want to arrive in style.

3.Maysville Oktoberfest – Maysville, KY

Located in historic downtown Maysville, the Maysville Oktoberfest is an iconic fall event in Kentucky.

Celebrate German heritage while enjoying the country’s traditional food, beer, wine, and liquor.

Once you’ve had your fill, check out one of the competitions for the brave of heart. Join the log sawing contest or the stein hoisting competition for a chance to win prizes and bragging rights.

Take a stroll through the German auto show where owners of fine automobiles show-off their German-made cars.

The kids can have fun too. Maysville Oktoberfest offers games and crafts for kids so the whole family can have a fun fall day.

4.Woolly Worm Festival – Beattyville, KY

For a truly unique KY fall festival look no further.

Attendees of the Woolly Worm Festival have been witnessing the prediction of the upcoming winter for over 40 years. The 13 segments of the caterpillar are used to give us warning about each of the 13 weeks in winter.

Several one-of-a-kind events are put on every year including the exciting woolly worm race and the infamous reading of the woolly worm.

Join the crowd of over 17,000 fans giving a fond and fun farewell to Fall and the Kentucky Thanksgiving season.

Family, Friends, and Fall

With so much to do in Kentucky during the fall, the season feels magical. From fall weddings and scenic tours of famous bourbon distilleries to lively festivals, there’s something for everyone.

Take in the crisp autumn weather, stunning natural beauty, and the unique charm of Kentucky’s events. If you’re heading to a fall festival in Lexington or beyond, let us handle your transportation so you can focus on enjoying the season stress-free.