Jail Break 5K
- Date Sat 25th October 2025
- Time 8:00AM EDT
- Location Saint Augustine, Florida
- Price $27.50 - $48.70
- Races 2 races
- Distances 5km
Event summary
Get ready for an exhilarating experience at the Jail Break 5K, set to take place on Saturday, October 25, 2025, in the historic charm of St. Augustine, Florida. This exciting race kicks off at 8:00 AM at the iconic Old Jail, where runners and walkers will embark on a scenic route that takes them through beautiful Magnolia Avenue and over the stunning Vilano Bridge, ending at the breathtaking Atlantic Ocean.
Participants can choose to join in-person or take part virtually, with entry fees starting as low as $25 if you register before April 21. This event not only promises a fun-filled day with a costume contest, family-friendly activities, and a unique themed course, but it also supports a great cause—proceeds benefit Investing in Kids (INK!), which provides essential resources for local public school students and teachers. With awards for top finishers and exciting post-race festivities, the Jail Break 5K is a fantastic opportunity to enjoy a lively community atmosphere while making a positive impact. Don’t miss this chance to run for a cause and have a blast in St. Augustine!
Participants can choose to join in-person or take part virtually, with entry fees starting as low as $25 if you register before April 21. This event not only promises a fun-filled day with a costume contest, family-friendly activities, and a unique themed course, but it also supports a great cause—proceeds benefit Investing in Kids (INK!), which provides essential resources for local public school students and teachers. With awards for top finishers and exciting post-race festivities, the Jail Break 5K is a fantastic opportunity to enjoy a lively community atmosphere while making a positive impact. Don’t miss this chance to run for a cause and have a blast in St. Augustine!
Organiser's Description
JAIL BREAK 5K
PROCEEDS FROM THE JAIL BREAK 5K BENEFIT INVESTING IN KIDS (INK!) [http://www.ink-stjohns.org].
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 25, 2025 - 8:00 AM
WHERE
THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail]
167 San Marco Avenue
St. Augustine, FL 32084
ENTRY FEES
Until April 21 = $25 (Special pricing!)
April 22 - June 21 = $30
June 22 - September 6 = $35
September 6 - October 24 = $40
Race Day - October 25 =$45
VIRTUAL ONLY = $45
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 24th at Packet Pick Up or we will ship your swag to you after the race. There will be no awards for the virtual race.
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.
SCHEDULE OF EVENTS
PRE-RACE PACKET PICK UP/REGISTRATION: Friday, Oct. 24, 2025, 4:30 - 6:30 PM OLD TOWN WELCOME CENTER [https://www.google.com/maps/place/Old+Town+Trolley+Welcome+Center+US-1/@29.9037457,-81.320061,19z/data=!4m13!1m7!3m6!1s0x88e427bee7fef045:0xcd367c4244f64e4c!2s27+San+Marco+Ave,+St.+Augustine,+FL+32084!3b1!8m2!3d29.8999605!4d-81.314527!3m4!1s0x88e427c883b9d647:0x1a554cef233a8f94!8m2!3d29.9039935!4d-81.3211001], 1305 North Ponce De Leon Blvd. St. Augustine, FL 32084
RACE DAY PACKET PICK UP: Saturday, Oct. 25, 2025, 6:30 - 7:30 AM - THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail],167 San Marco Ave, St. Augustine, FL 32084
RACE START: Saturday, October 25, 2025 - 8:00 AM - THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail],167 San Marco Ave, St. Augustine, FL 32084
JAIL BREAK AFTER PARTY: Saturday, October 25, 2025 - 9:00 AM - 10:30 AM at THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail], 167 San Marco Ave., St. Augustine, FL 32084
PARKING
Free parking is available at the Old Town Trolley Depot,167 San Marco Ave. in St. Augustine. Paid parking is available at the Historic Downtown Parking Facility, adjacent to the Visitor Information Center at 1 Cordova St. in downtown St. Augustine.
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, 2025.
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 [http://racesmith.com/]
FOR MORE INFORMATION
Email: [email protected]
PROCEEDS FROM THE JAIL BREAK 5K BENEFIT INVESTING IN KIDS (INK!) [http://www.ink-stjohns.org].
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 25, 2025 - 8:00 AM
WHERE
THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail]
167 San Marco Avenue
St. Augustine, FL 32084
ENTRY FEES
Until April 21 = $25 (Special pricing!)
April 22 - June 21 = $30
June 22 - September 6 = $35
September 6 - October 24 = $40
Race Day - October 25 =$45
VIRTUAL ONLY = $45
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 24th at Packet Pick Up or we will ship your swag to you after the race. There will be no awards for the virtual race.
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.
SCHEDULE OF EVENTS
PRE-RACE PACKET PICK UP/REGISTRATION: Friday, Oct. 24, 2025, 4:30 - 6:30 PM OLD TOWN WELCOME CENTER [https://www.google.com/maps/place/Old+Town+Trolley+Welcome+Center+US-1/@29.9037457,-81.320061,19z/data=!4m13!1m7!3m6!1s0x88e427bee7fef045:0xcd367c4244f64e4c!2s27+San+Marco+Ave,+St.+Augustine,+FL+32084!3b1!8m2!3d29.8999605!4d-81.314527!3m4!1s0x88e427c883b9d647:0x1a554cef233a8f94!8m2!3d29.9039935!4d-81.3211001], 1305 North Ponce De Leon Blvd. St. Augustine, FL 32084
RACE DAY PACKET PICK UP: Saturday, Oct. 25, 2025, 6:30 - 7:30 AM - THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail],167 San Marco Ave, St. Augustine, FL 32084
RACE START: Saturday, October 25, 2025 - 8:00 AM - THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail],167 San Marco Ave, St. Augustine, FL 32084
JAIL BREAK AFTER PARTY: Saturday, October 25, 2025 - 9:00 AM - 10:30 AM at THE OLD JAIL [https://www.trolleytours.com/st-augustine/old-jail], 167 San Marco Ave., St. Augustine, FL 32084
PARKING
Free parking is available at the Old Town Trolley Depot,167 San Marco Ave. in St. Augustine. Paid parking is available at the Historic Downtown Parking Facility, adjacent to the Visitor Information Center at 1 Cordova St. in downtown St. Augustine.
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, 2025.
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 [http://racesmith.com/]
FOR MORE INFORMATION
Email: [email protected]
Races
-
Jail Break 5K
Incl. $2.50 Fee & T-Shirt
Sat 25th October 2025 (8:00AM EDT)
$27.50
OPENS SOON -
Jail Break 5K VIRTUAL
Incl. $3.70 Fee & T-Shirt
$48.70
OPENS SOON
Reviews
Done this event?
First-hand event reviews from people who have been there, done that and got the breathable T-shirt, really help everyone choose their next event.
Add a reviewJail Break 5K