10th Annual Jail Break 5K

Old Town Trolley Tours and INK! (Investing in Kids) present the 10th Annual Jail Break 5K on Saturday, October 24, 2026. The race starts at 8:00 a.m. The Jail Break After Party starts at 9:00, after the race, and continues until 10:30 a.m.

At this Halloween event, runners "escape" from the authentic Old Jail and race across the Vilano Bridge to the Atlantic Ocean. Because this is a one-way race, runners can use the shuttle transportation at the finish to return to the Old Jail for the after-party. Runners of all ages and abilities are welcome. The race organizers have water stations at the first and second mile markers and at the finish.

The post-race festivities include a costume contest sponsored by the Ghosts and Gravestones Tour. Run or walk in costume and perhaps win a cash prize. Local celebrity judges award first, second, and third prizes for costumes in two categories: adults and youth.

Register with your public school and compete as a team of students, families, friends, faculty, and staff. The school with the most participants receives a trophy and $1,000.00 for the school.

Beneficiary

Proceeds from the Jail Break 5K benefit Investing in Kids (INK!). 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.

Event Details

Registration: Tickets range from $25.00 to $45.00, depending on your registration date. Register online at runsigup.com.

When: Saturday, October 24, 2026, 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, 167 San Marco Avenue, St. Augustine, Florida 32084

Packet Pickup: 

• Friday, October 23, 2026, from 4:30 to 7:30 p.m., at the Old Town Welcome Center at 1305 North Ponce De Leon Blvd. St. Augustine, Florida 32084
• Race Day, October 24, 2026, 6:30 to 7:30 a.m., at The Old Jail, 167 San Marco Avenue, St. Augustine, Florida 32084

Race Timing and Scoring: The race is professionally scored by Hasselmania Productions, LLC. All competitors have electronic tags attached to their bib number, and must wear their bib in front, pinned at all four corners.

Other Races

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.

All photos courtesy of Old Town Trolley Tours.