Jail Break 5K

Old Town Trolley Tours and INK! (Investing in Kids) present the 9th Annual Jail Break 5K on Saturday, October 25, 2025 at 8:00 a.m.

At this Halloween event, runners "escape" from the authentic Old Jail and race across the Vilano Bridge to the Atlantic Ocean. Runners of all ages and abilities are welcome, and everyone is invited to dress up for the occasion. There's plenty to do for non-runners too with post-race festivities that include a costume contest sponsored by the Ghosts and Gravestones Tour.

Whether you're into marathons, half-marathons, themed runs, or chasing a new personal record during 5K and 10K races, St. Augustine has a full schedule of races for your next challenge.

Admission: Tickets range from $25.00 to $45.00 depending on registration date. Register online.

When: Saturday, October 25, 2025, beginning at 8:00 a.m. with a jail break after party from 9:00 a.m. to 10:30 a.m. at the Old Jail.

Where: The Old Jail is located at 167 San Marco Avenue in St. Augustine, Florida 32084.

Packet Pickup: Friday, October 24, 2025, from 4:30 to 6:30 p.m. at the Old Town Welcome Center at 1305 North Ponce De Leon Blvd. St. Augustine, Florida 32084

About INK! (Investing in Kids): INK! provides innovative programs and classroom resources to promote academic success for all public school students in St. Johns County. Proceeds from the annual race support the teachers and students.

All photos courtesy of Old Town Trolley Tours.