Old Town Trolley Tours: Jail Break 5K
- When: Saturday, October 24, 2026, 8:00 am
- Location: Old Jail, 167 San Marco Ave, St. Augustine, FL 32085
- Cost: $35+
Join INK! (Investing in Kids) and Old Town Trolley Tours of St. Augustine as we 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, we're making our 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.
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
- Website: www.facebook.com
- Category: Races, Walks, 5Ks
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