Jail Break 5K 2026

Jail Break 5K 2026 & Halloween Costume Contest
All runners and walkers are welcome to participate in the 10th Annual Jail Break 5K Run for A Cause!  During the race, the traditional Jail Break 5K Halloween Costume Contest will take place.  Run/walk in costume to win one of the cash prizes.
When: Saturday, October 24, 2026 — 8:00am
Course Info
“Escape” from the historic Old Jail in uptown St. Augustine, proceed through scenic Magnolia Avenue and over the Vilano Bridge to the Atlantic Ocean.  Transportation via shuttle for all racers will be provided at the finish of the race back to the start.
There’s also a virtual option if you can’t “Escape” in person.
Race Info
Beautiful finisher’s medal, distinctive t-shirt, unique themed course, a Halloween costume contest, refreshments, and family fun!  Availability and size of shirts only guaranteed to those who register by September 30, 2026.
Water stations at the start, 1 mile, 2 mile, and finish.
5K USATF Certified Course # FL17069TY.
Proceeds from the race will benefit INK! Investing in Kids.  Our mission: To provide innovative programs and classroom resources to promote the academic success of St. Johns County public school students.
Entry Fee:
$25.00 — until May 31
$30.00 — June 1 – July 31
$35.00 — August 1 – October 16
$40.00 — October 17 – October 23
$45.00 — October 24 – Race Day
$40.00 – Virtual Option
Click on the event website link to register and for all additional information.