Jail Break 5K 2026

The Jail Break 5K begins at the Old Jail in St. Augustine, Florida, with participants departing at 8:00 a.m. in Halloween costumes. This themed 5K is presented by Old Town Trolley Tours and INK!, with race proceeds benefiting St. Johns County public school students via INK! programs and classroom resources. The course follows the jail-break concept: runners "escape" the historic Old Jail, cross the Vilano Bridge, and proceed toward the Atlantic Ocean. The event is open to runners of all ages and abilities. The morning concludes with a post-race gathering and a costume contest sponsored by the Ghosts and Gravestones Tour. Packet pickup occurs the day before at the Old Town Welcome Center, and registration can be completed online.