Jail Break 5K
Participants run or walk a certified 5K course starting at the historic Old Jail, traveling down Magnolia Avenue and crossing the Vilano Bridge toward the Atlantic Ocean. The race grounds host food trucks, vendors, photo booths, and an after-party with an awards ceremony. Attendees can also participate in a Halloween costume contest evaluated by local celebrity judges.
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Plan Your Visit
Website / Tickets
When
Tickets
In-person entry: $25 through May 31; $30 June 1–July 31; $35 August 1–October 16; $40 October 17–23; $45 on race day, October 24. Runners ages 4–18 are $25 if registered by October 23. T-shirts are guaranteed only for registrations by September 30. The $40 virtual option is a separate event and is not included here.
Hours
Race starts at 8:00 AM. Race-day packet pickup is 6:30–7:30 AM; the after party is 9:00–10:30 AM.
Ages
All ages welcome (special pricing for ages 4-18)
Neighborhood
Uptown St. Augustine
Food & Drink
Food trucks, event refreshments, and multiple on-course water stations are available for participants.
Parking
Free parking is available at Old Town Trolley parking lots across the street on San Marco Avenue, on Dufferin Street adjacent to the Old Jail, at 1305 N. Ponce De Leon Blvd., and at 1700 Ponce De Leon Blvd. Parking is also available at the Historic Downtown Parking Facility by the Visitor Information Center. The Old Jail parking lot is closed for parking on event day.
Going?
Location
Tips & Advice
- Park at the nearby Old Town Trolley lots or on Dufferin Street, as the Old Jail lot is closed to vehicles for race activities.
- Register by September 30 to guarantee your t-shirt size and availability.
- Pin your race bib securely at all four corners on your front so the electronic timing tag reads properly.
Special Events & Promotions
- Runners ages 4–18 pay $25 if registered by October 23, 2026.
Links & Contact
Run by Investing in Kids (INK!)
Halloween Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.
Frequently Asked Questions
Can participants walk the course instead of running?
Yes, both runners and walkers are welcome to participate in the race.
Is there a costume contest?
Yes, there is a costume contest with cash prizes awarded to the top three adult and top three youth participants.
How do participants return to the start line after finishing?
Shuttle transportation is provided at the finish line to take all racers back to the starting area.
Are water stations available on the course?
Water stations are positioned at the start, at the 1-mile mark, at the 2-mile mark, and at the finish line.
What is the policy if the race is affected by bad weather?
If the event is canceled or postponed due to inclement weather, emergencies, or natural disasters, refunds are not provided.
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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. Halloween Events Near Me is an independent guide and isn't affiliated with the events we list.