Christmas at Shaker Village

Distance from Backroads & Barrels: Approximately 25 minutes
Address: 3501 Lexington Road, Harrodsburg, KY 40330
Website: https://shakervillageky.org

Celebrate the holiday season with festive events, shopping, seasonal dining, historic demonstrations, and special activities throughout Shaker Village of Pleasant Hill from Annually from late November through December.

Great American Brass Band Festival

Distance from Backroads & Barrels: Approximately 25 minutes
Address: Downtown Danville, KY 40422
Website: https://gabbf.org

Held each June, this nationally recognized music festival brings brass bands from across the country to downtown Danville for free performances, local food vendors, and family-friendly entertainment.

Pioneer Playhouse Summer Season

Distance from Backroads & Barrels: Approximately 25 minutes
Address: 840 Stanford Road, Danville, KY 40422
Website: https://pioneerplayhouse.com

Kentucky's oldest outdoor theater offers live performances, dinner theater, and family-friendly entertainment throughout the summer season.

Wildside Winery Events

Distance from Backroads & Barrels: Approximately 20 minutes
Address: 5500 Troy Pike, Versailles, KY 40383
Website: https://wildsidewinery.com

Wildside Winery hosts live music, wine tastings, food trucks, seasonal celebrations, and special events throughout the year in a relaxed vineyard setting.

Pioneer Days

Distance from Backroads & Barrels: Approximately 15 minutes
Address: Old Fort Harrod State Park, 100 S. College Street, Harrodsburg, KY 40330
Website: https://visitharrodsburgky.com/events/pioneer-days-2/

Held annually in August, Pioneer Days brings live music, food and craft vendors, a car show, a 5K run/walk, and family-friendly activities to the historic grounds of Old Fort Harrod State Park.

Keeneland Spring & Fall Meets

Distance from Backroads & Barrels: Approximately 35 minutes
Address: 4201 Versailles Road, Lexington, KY 40510
Website: https://keeneland.com

One of Kentucky's most anticipated spring traditions, the Keeneland Spring Meet features world-class Thoroughbred racing, beautiful grounds, shopping, dining, and an unforgettable horse country experience.

Kentucky Bourbon Festival

Distance from Backroads & Barrels: Approximately 1 hour 15 minutes
Address: Bardstown, KY 40004
Website: https://kybourbonfestival.com

One of Kentucky's most popular bourbon events, featuring tastings, distillery experiences, live entertainment, food vendors, educational sessions, and special releases from many of the state's best-known bourbon brands. Held annually in September, this ticketed event is for guests age 21 and older, and advance reservations are strongly recommended.

Looking for More Events?

Event schedules change throughout the year. For additional festivals, community events, seasonal celebrations, and special events throughout Kentucky, visit:

Kentucky Festival Guides & Reviews
https://festivalguidesandreviews.com/kentucky-festivals/