👟10 Years. Thousands of Runners. One Epic Escape. 🚔
Join INK! (Investing in Kids) and Old Town Trolley Tours of St. Augustine as they celebrate the 10th Annual Jail Break 5K on Saturday, October 24, 2026!
For a decade, runners, walkers, families, and community supporters have gathered for one of St. Augustine's most unique and entertaining races. This year, they’re making the biggest escape yet! ⛓️💥🏃♂️💨
Lace up your running shoes and break free from the historic Old Jail Museum, a 130-year-old landmark, as you race through the beautiful streets of the Nation's Oldest City. Cross the scenic Vilano Bridge and make your getaway to the beach and the finish line beyond. 👟🏃🏁
🏁 Race Start: 8:00 a.m.
📍 Location: Old Jail, 167 San Marco Avenue, St. Augustine
⏱️ Course: USATF-certified, chip-timed 5K
But the fun doesn't stop at the finish line!
🎶 Enjoy live music and entertainment along the course
🎭 Show off your creativity in our crowd-favorite costume contest
🏆 Compete for cash prizes for best adult and youth costumes
🎉 Celebrate your freedom at the post-race after-party
👕 Receive a commemorative 10th Anniversary race shirt
🏅 Earn a unique finisher medal to mark your escape
🏫 School Team Challenge
Calling all St. Johns County public schools!
Gather your students, families, teachers, staff, alumni, and supporters for the Jail Break 5K School Team Challenge.
🥇 The public school team with the most registered participants will win:
✅ $1,000 for their school
✅ The coveted Jail Break 5K Team Challenge Trophy
✅ Year-long bragging rights
🥈🥉 Second- and third-place school teams will also earn cash prizes and community bragging rights.
💙 Run for a Reason 💙
Every step supports INK!'s mission to connect community to classrooms, support innovative teaching and learning, empower student potential, and celebrate success throughout St. Johns County schools.
Whether you're chasing a personal best, walking with friends, competing in costume, or supporting your school, the Jail Break 5K is a race you won't want to miss!
🚨 The Sheriff is waiting. Don't get caught!