Jail Break 5K
Embark on a thrilling escape at the Jail Break 5K in Saint Augustine! This unique race begins and ends at the historic Old Jail, taking participants on a scenic route over the Vilano Bridge. Don your best costume for a chance to win cash prizes in the dedicated Halloween Costume Contest. Proceeds from this exciting event support Investing in Kids (INK!), benefiting local students and teachers.
Other Halloween Near Saint Augustine
What to Expect
Escape from the historic Old Jail.
Know Before You Go
- Tickets: $35 – Get tickets
- Parking: Free parking available at multiple Old Town Trolley lots on San Marco Avenue, Dufferin Street, 1305 N. Ponce De Leon Blvd., 1700 Ponce De Leon Blvd., and the Historic Downtown Parking Facility. The Old Jail parking lot will be closed for race activities.
- Pets: No pets allowed (service animals welcome)
Local Insight & Ratings
Scare Factor
Family Friendly
Best For
Runners, walkers, families, costume enthusiasts
Vibe
Themed, community-oriented, active, fun
Energy Level
Moderate
Budget
$$
Photo Friendly
High
Weather Sensitivity
Moderate
Special Events & Promotions
- Price increases after October 14, 2025
- Special pricing available until April 30
- Virtual race option available
- Costume contest with cash prizes
- Public School Team Challenge with awards and prize money
Location
Event Details
Duration
Approximately 2-3 hours for the race and after party
Ages
All ages
Timed Entry
No
Organizer
Investing in Kids (INK!)
Food & Drink
Vendors and food trucks available on-site.
Quick Actions
Tips & Advice
- Register by September 30, 2025, to guarantee your preferred t-shirt size.
- Arrive early on race day to pick up your packet and explore the vendors and photo booths before the 8:00 AM start.
- Consider the virtual option if you can't make it to Saint Augustine on October 25th; you can still participate and receive race swag.
- Plan your parking in advance, as the Old Jail lot will be closed for race activities, but several free alternatives are available nearby.
- Check the pricing tiers; early registration offers significant discounts on entry fees.
Frequently Asked Questions
What is the Jail Break 5K?
The Jail Break 5K is a themed 5K run/walk event held annually in Saint Augustine, Florida, starting and ending at The Old Jail, with proceeds benefiting local education initiatives.
When and where does the race take place?
The race is scheduled for Saturday, October 25, 2025, starting at 8:00 AM at The Old Jail, located at 167 San Marco Avenue, Saint Augustine, FL 32084.
Are there any special requirements for participants?
Participants are encouraged to wear costumes for the costume contest. The course is USATF certified and suitable for runners and walkers of all ages.
What is the fundraising aspect of this event?
Proceeds from the Jail Break 5K directly benefit Investing in Kids (INK!), a non-profit organization dedicated to supporting St. Johns County public school students and teachers.
What happens if there is bad weather?
In the event of inclement weather, emergency, or natural disaster, the race organizers reserve the right to cancel or postpone the event. Refunds will not be issued in such cases.
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.