Jail Break 5K

Proceeds

Proceeds from the Jail Break 5K benefit Investing in Kids (INK!).

Mission

• Objective: To provide innovative programs, teacher support, and classroom resources.
• Goal: 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: $45
• Virtual Only: $40

Virtual Race

Can't #ESCAPE with us on October 25? 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 at 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 at The Old Jail, 167 San Marco Ave, St. Augustine, FL 32084
• Race Start: Saturday, October 24, 2026 - 8:00 AM at 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 2025 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.