Jail Break 5K
About This Event
**Proceeds from the Jail Break 5K benefit Investing in Kids (INK!). **
**Our mission: **To provide innovative programs, teacher support, and classroom resources to promote success for all St. Johns County public school students and teachers.
WHEN
Saturday, October 24, 2026 - 8:00 AM
WHERE****
The Old Jail 167 San Marco Avenue St. Augustine, FL 32084
ENTRY FEES
Until May 31 = $25 (Special pricing!) June 1 - July 31 = $30 August 1 - October 16 = $35 October 17 - October 23 = $40
Race Day - October 24 =$45
VIRTUAL ONLY = $40
**VIRTUAL RACE
**
Can't #ESCAPE with us on October 24? Make your escape virtually! Sign up for the Jail Break 5K VIRTUAL option and submit your results to RunSignUp. You can pick up your JB5K race swag on October 23rd at Packet Pick Up or we will ship your swag to you after the race. There will be no awards for the virtual race.
SCHEDULE OF EVENTS
Pre-Race Packet Pick Up/Registration: Friday, Oct. 23, 2026, 4:30 - 6:30 PM Old Town Welcome Center, 1305 North Ponce De Leon Blvd. St. Augustine, FL 32084
Race Day Packet Pick Up: Saturday, Oct. 24, 2026, 6:30 - 7:30 AM - The Old Jail,167 San Marco Ave, St. Augustine, FL 32084
Race Start: Saturday, October 24, 2026 - 8:00 AM - The Old Jail,167 San Marco Ave, St. Augustine, FL 32084
**Jail Break After Party: **Saturday, October 24, 2026 - 9:00 AM - 10:30 AM at The Old Jail, 167 San Marco Ave., St. Augustine, FL 32084
**PARKING
**
Free parking is available at Old Town Trolley parking lots on San Marco Avenue across the street from the Old Jail, on Dufferin Street, adjacent to the Old Jail, at 1305 N. Ponce De Leon Blvd., and 1700 Ponce De Leon Blvd. in St. Augustine. Parking is also available at the Historic Downtown Parking Facility, adjacent to the Visitor Information Center at 1 Cordova St., St. Augustine.
The Old Jail parking lot at 167 San Marco Street will be closed for parking to allow space for runners and walkers to safely warm-up and explore our vendors, food trucks, photo booths and selfie stations, and enjoy the post-event awards ceremony and festivities.
COURSE
Runners and walkers are welcome to escape with us from the historic Old Jail, in uptown St. Augustine! Starting at the Old Jail, run through beautiful Magnolia Avenue and over the Vilano Bridge to make your escape to the Atlantic Ocean. Shuttle transportation for all racers will be provided at the finish returning to the start.
There will be water stations at the start, 1 mile, 2 mile, and finish.
The Jail Break 5K is a 5K USATF Certified Course # FL17069TY.
**AMENITIES
**
Beautiful finisher's medal, distinctive t-shirt, unique themed course, with costume contest, refreshments, and family fun. Availability and size of t-shirts only guaranteed to those who register by September 30, 2026.
AWARDS
Overall Male and Female finishers and the top three runners in the following age groups: 9 and under, 10-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54, 55-59, 60-64, 65-69, 70-74, 75 and older.
**COSTUME CONTEST
**
The Jail Break 5K Halloween Costume Contest will again take place at the Jail Break 5K 2026 race! Run/walk in costume to win a cash prize! Prizes will be awarded for the top three (3) costumed adult participants and the top three (3) youth participants. The Costume Contest will be determined by a panel of local celebrity judges.
**PUBLIC SCHOOL TEAM CHALLENGE
**
St. Johns County Public Schools are invited to register students, families, friends, faculty, and staff as a team in the Jail Break 5K Team Challenge. The public school with the highest number of registered participants will receive a one-of-a kind Jail Break 5K Team Challenge trophy, bragging rights, and a $1,000 award for your school! Prize money will also be awarded to the 2nd and 3rd place public school teams registering the 2nd and 3rd highest number of event participants.
RACE TIMING AND SCORING
The race will be professionally timed and scored by Hasselmania Productions LLC. The race will be timed using disposable, electronic tags attached to the bib number. Please wear your bib number to the front, pinned at all four corners, visible, and unaltered. Printed results will be posted at the race site and live online during the race at www.RaceSmith.com
CANCELLATION POLICY
In the event of inclement weather, emergency or a natural disaster, INK! reserves the right to cancel or postpone the race. In the event of cancellation or postponement, there will be no refunds.
Ready to run?
Weather
Frequently Asked Questions
When is Jail Break 5K 2026?
Where does Jail Break 5K take place?
How do I register for Jail Break 5K?
Is there a promo code for Jail Break 5K?
Get Race Updates & Training Tips
Join thousands of Florida runners. Weekly updates on races, training tips, and local running news.
Registration
Registration links may earn us a small commission at no extra cost to you.
Local Running Stores
Clermont, Central Florida
Dash Sports is Clermont's specialty running and walking shoe store, serving the South Lake County running community from its location on West Montrose Street in downtown Clermont. The store takes a thorough approach to fitting — each customer receives a custom gait and foot analysis that typically runs 20 to 40 minutes, ensuring the shoe recommendation is grounded in how you actually move. Clermont's reputation as a triathlon and endurance sports hub makes Dash Sports a natural resource for serious athletes alongside everyday runners and walkers. The store carries a strong lineup of performance brands including Hoka, On Running, Brooks, New Balance, and Altra, giving customers access to the leading options in road, trail, and stability footwear. Dash Sports also stocks Olukai and Aetrex for customers seeking comfort and orthopedic options alongside performance footwear — rounding out a selection that serves runners, walkers, and recovery-focused athletes alike.
phone (352) 394-7434 language Visit WebsiteAltamonte Springs, Central Florida
Fit2Run Altamonte Springs is located in Altamonte Mall, bringing the Runner's Superstore experience to Seminole County. Offering gait analysis, top performance footwear, and community run events for the growing north Orlando running community.
phone (844) 348-2786 language Visit WebsiteLake Buena Vista, Central Florida
Fit2Run at Disney Springs is the only running specialty store inside the Walt Disney World Resort destination. Open late to serve resort guests and locals alike, offering gait analysis, top performance brands, and a one-of-a-kind running store experience in the heart of Central Florida tourism.
phone (407) 743-5990 language Visit WebsiteJail Break 5K
October 24, 2026