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Falling for Kentucky: The Best Festivals of the Season
- larissalongg
- 17 minutes ago
- 3 min read
By Larissa Long
Fall in Kentucky has a way of making everything feel a little more special. The air is crisp, the leaves are changing, and weekends are perfect for getting out and enjoying the season. From pumpkin patches and orchard adventures to live music and local food, fall festivals are the best way to experience the sights, sounds, and flavors of the Bluegrass.
At Kentucky Taste Buds, we’ve gathered some of our favorite festivals happening this September and October. There’s something for everyone—family-friendly fun, foodie finds, and a few events you’ll want to plan your weekend around.
🍁 September Festivals
Photo courtesy of GotLouisville.com
🎸Louder Than Life
Date: September 18th-21st
Location: Louisville, KY
If rock music and bourbon are your jam, Louder Than Life is basically heaven. With over 175 bands, gourmet food, and bourbon tastings, it’s worth planning a whole weekend around. Learn more
Photos courtesy of Shaker Village
🪔Shaker Village Harvest Fest
Date: September 20th-21st
Location: Harrodsburg, KY
Step back in time with traditional crafts, seasonal foods, and historic charm. It’s cozy, family-friendly, and a picture-perfect fall weekend. Details here
Photo courtesy of Old North Bar
🐾 Furry Finds Fall Market
Date: Septemeber 20th
Location: Lexington, KY
A pet-lover’s dream! Shop for your furry friends, enjoy food trucks, and even meet adoptable animals. Event info
Photo courtesy of Midway Fall Festival
🎨 Midway Fall Festival
Date: September 20th-21st
Location: Midway, KY
Arts, crafts, local food, and live music fill this charming small-town festival. Perfect for a laid-back weekend stroll. Visit site
Photo courtesy of Casey County Apple Festival
🍎 Casey County Apple Festival
Date: September 25th-27th
Location: Liberty, KY
Live music, parades, contests, and the world’s largest apple pie! A mix of small-town charm and tasty fall fun. Festival info
Photo courtesy of Jessamine Fall Festival
🎡 Jessamine Fall Festival
Date: September 26th-27th
Location: Nicholasville, KY
Food trucks, craft vendors, parades, and family activities all come together at this community celebration. More details
Photo courtesy of Old North Bar
🎧 Old North Bar Silent Disco
Date: September 27th
Location: Lexington, KY
Grab your headphones and dance the night away with three channels of music and fall drink specials. Check it out
Photo courtesy of runsignup.com
🏃♂️ Raven 10K Trail Run
Date: September 28th
Location: Lexington, KY
Run, jog, or walk through gorgeous fall scenery at Raven Run Nature Sanctuary. Sign up
🎃 October Festivals
Photo courtesy of Jack O'Lantern Spectacular
🕯️ Jack O'Lantern Spectacular
Date: October 2nd-November 2nd
Location: Louisville, KY
Thousands of glowing pumpkins create a magical trail at Iroquois Park. Perfect for families or a spooky date night. See more
Photo courtesy of St. James Court Art Show
🎭 St. James Court Art Show
Date: October 3rd-5th
Location: Louisville, KY
One of the country’s biggest art shows with 700+ artists, live music, and food vendors. Visit site
Photo courtesy of Woodford Humane
🐎 Keeneland Fall Meet
Date: October 3rd- 24th
Location: Lexington, KY
A Kentucky tradition! Horse racing, tailgating, and autumn energy you don’t want to miss. Tickets here
Photo courtesy of Wildside Winery
🍷 Pumpkin Festival at Wildside Winery
Date: October 11th-12th
Location: Versailles, KY
Sip pumpkin-spiced wines, browse local vendors, and enjoy vineyard views. More info
Photo courtesy of Eckert's
🌾 Eckert's Pumpkin Jamboree
Date: October 26th
Location: Versailles, KY
Pumpkin picking, hayrides, and seasonal treats make this a family favorite. Festival details
Whether you’re chasing live music, apple pies, or pumpkin patches, Kentucky’s fall festivals have something for everyone. Grab your friends or family, get outside, and make the most of this season. And if you go, don’t forget to tag @KYTasteBuds so we can share your adventures!
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