Louisville shines in the fall with bourbon, art, music, and plenty of spooky fun. Here’s your guide to the city’s best festivals and seasonal happenings.
September
Monday, September 1 – All Month
National Bourbon Heritage Month
Citywide | Louisville
Celebrate Kentucky’s signature spirit with tastings, tours, and special bourbon-themed events across the city.
Friday, September 5 – Sunday, September 7
Kentucky Bourbon Festival
Bardstown, KY | kentuckybourbonfestival.com
One of bourbon country’s biggest festivals, with tastings, dinners, and the legendary barrel relay race.
Friday, September 5 – Saturday, September 6
Middletown Family Fun Festival
Middletown, KY
Small-town charm with vendors, live entertainment, and a community parade.
Friday, September 5 – Saturday, September 6
Oktoberfest at the German-American Club
German-American Club | Louisville
German beer, brats, and live polka bands bring Bavaria to Louisville.
Saturday, September 6
Greater Louisville Hamfest
Louisville area
Kentucky’s largest gathering of ham radio enthusiasts.
Saturday, September 6 – Sunday, September 7
Big Four Arts Festival
Big Four Lawn, Waterfront Park
Juried art from over 150 artists, plus music and food along the riverfront.
Saturday, September 6 – Sunday, September 7
Fleur de Flea Vintage Urban Market
Waterfront Park
A treasure hunter’s paradise of vintage goods, retro finds, and quirky collectibles.
Saturday, September 6 – Sunday, September 7
Trimble County Apple Festival
Trimble County Courthouse | Bedford, KY
Apple pies, ciders, crafts, and a classic small-town fall vibe.
Saturday, September 6
Louisville Pride Festival
Bardstown Road | Highlands
A vibrant celebration of Louisville’s LGBTQ+ community with music, food, and parade.
Thursday, September 11 – Sunday, September 14
Bourbon & Beyond
Highland Festival Grounds | Kentucky Exposition Center
A multi-day festival pairing world-class bourbon tastings with headline music acts.
Saturday, September 13
Bike to Beat Cancer
Norton Cancer Institute Brownsboro | Louisville
Cyclists ride to raise funds for cancer care and research.
Saturday, September 13
Simpsonville Fall Festival
Simpsonville, KY
Local crafts, music, and seasonal family activities.
Thursday, September 18 – Sunday, September 21
Louder Than Life
Highland Festival Grounds | Kentucky Exposition Center
The nation’s largest rock festival with huge acts, bourbon, and food trucks.
Friday, September 26 – Sunday, September 28
Pumpkins at Kentucky Kingdom
Kentucky Kingdom | Fairgrounds
Family-friendly Halloween fun with pumpkin displays, trick-or-treating, and live shows.
Sunday, September 28 – Thursday, October 30
Boo at the Zoo
Louisville Zoo
A beloved tradition with costumed characters, trick-or-treat paths, and glowing pumpkin displays.
October
Friday, October 3 – Sunday, October 5
St. James Court Art Show
Old Louisville
One of the nation’s premier art shows, with hundreds of artists lining the historic streets.
Thursday, October 2 – Saturday, November 1
Jack O’ Lantern Spectacular
Iroquois Park
Thousands of artist-carved pumpkins light up a glowing forest trail.
Friday, October 10 – Saturday, October 11
Belknap Fall Festival
Douglass Loop | Highlands
Live music, art vendors, and family fun in a historic neighborhood.
Friday, October 10 – Saturday, October 11
Garvin Gate Blues Festival
Garvin Place & Oak Street | Old Louisville
Two nights of live blues in one of Louisville’s most atmospheric districts.
Saturday, October 18
Urban Bourbon Half Marathon
Downtown Louisville to Cherokee Park
A scenic 13.1-mile run followed by bourbon tastings and post-race celebrations.
Saturday, October 18 – Sunday, October 19
Via Colori Street Painting Festival
Big Four Bridge | Waterfront Park
Watch artists transform pavement into massive chalk masterpieces.
October (Dates TBA)
Louisville’s International Festival of Film
Muhammad Ali Center & Louisville Slugger Museum
Independent films from around the world, screened at iconic Louisville venues.
November
Thursday, November 13 – Sunday, November 23
North American International Livestock Exposition & Championship Rodeo
Freedom Hall, Kentucky Exposition Center
The world’s largest all-breed livestock show with rodeo competitions and family fun.
This article appears in Aug 1-31, 2025.