Bittersweet Festival

Bittersweet Festival is held the first weekend in October and includes music, parade, craft and food vendors, wrestling, contests, inflatables, zip line, dunking booth, and more! Craft & Food Vendors – Contact City Hall for an application at 606-256-3437 Schedule for 2026 Thursday, October 1 Car Show 4:30 PM to 8:00 PM in Lower Lot of Rockcastle County Courthouse Friday, October 2 Festival Hours 4:00 PM to 10:30 PM Music Schedule: 6PM: Jaclyn Bullock 7PM: Shane Winkler Band 8PM: Call to Post Saturday, October 3 Festival Hours 12:00 PM to 10:30 PM 11:00 AM Mountain Stampede Cloggers at Community Trust Bank 12:00 PM Parade down Main Street 3:30 – 5:30 PM Wrestling 4:00 PM Rockcastle Dance 5:00 PM: D Boone Pitman 6:00 PM: Donovan Howard 7:00 PM Best Beard and Best Mullet Contest 8:00 PM: Dukes of Country Also – Saturday Night we will have Best Beard and Best Mullet Contests at 7:00 PM at the main stage. Registration is on site at the main stage at 6:00 PM.