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St. Augustine Jail Break 5K Runners

Jail Break 5K Run for a Cause

Get ready to sprint, stroll, and support a great cause!

Ready to break out? The Jail Break 5K returns with the exhilaration of Halloween, offering you a chance to contribute to St. Johns County public school students through Investing in Kids (INK!). Begin your adventure at the historic Old Jail, dash down the charming Magnolia Avenue, and conquer the Vilano Bridge on your thrilling escape to the serene Atlantic Ocean. Once you’ve finished the race, no need to stress about the ride back – we’ve got you covered with a smooth trip on the Old Town Trolley.

What’s In Store

guests wearing jail break race shirts
Whether you're a speed demon or prefer a leisurely stroll, this event is for every member of the family.
Calling All Escapists
Jail Break race medal
Earn a medal that's a replica of famed Sheriff Perry's badge as a memento of your adventure.
Escape Artist Medal
Jail Break participants
In addition to the medal, everyone will receive a t-shirt (pictured).
Support a Cause

Get Ready

2023 Costume Quest

1st Place: $500 • 2nd Place: $300 • 3rd Place: $200

Put on your best Halloween attire and run/walk to win thrilling prizes.
Judges will pick the creepiest, funniest, and most creative costumes!


St. Augustine Jail Break costume judges

2022 Costume Contest Winners

2022 St. Augustine Jail Break 5K costume contest first place winner

First Place

2022 St. Augustine Jail Break 5K costume contest second place winner

Second Place

2022 St. Augustine Jail Break 5K costume contest third place winner

Third Place

Break Free in St. Augustine

Watch Our Video

and Experience the Jail Break 5K!

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2023 available now

Tickets & Schedule


Saturday, October 21, 2023.
8:00 am.


The Old Jail
167 San Marco Avenue
St. Augustine, FL 32084


Proceeds from the race will benefit Investing In Kids (INK!). Our mission: To provide innovative programs and classroom resources to promote the academic success of St. Johns County public school students.

INK, Old jail and Old Town Trolley logos

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