Jail Break 5K 2026

The race.

The Jail Break 5K takes place on Saturday, October 24, 2026, at 8:00 AM, starting and finishing at the Old Jail in Saint Augustine, Florida. The 5K course is USATF certified and runs through Magnolia Avenue and over the Vilano Bridge toward the Atlantic Ocean, with water stations at mile 1, mile 2, and the finish. Entry fees range from $25 (through May 31) to $45 (race day), with a virtual option available for $40. Packet pickup occurs Friday, October 23, from 4:30–6:30 PM at the Old Town Welcome Center, or Saturday morning from 6:30–7:30 AM at the Old Jail. Finishers receive a medal and t-shirt (sizes guaranteed for registrations by September 30), plus refreshments at the post-race celebration. Awards go to overall winners and top three finishers in age groups from 9 and under through 75 and older. Proceeds benefit Investing in Kids (INK!), which supports Saint Johns County public school programs and resources.