Escape the Old Jail at Old Town Trolley Tours Jail Break 5K
ST. AUGUSTINE, Florida (August 8, 2025) – St. Augustine’s spookiest 5K is taking off from the Old Jail at 167 San Marco Avenue in St. Augustine, on Saturday, October 25th. Old Town Trolley Tour®’s 9th Annual Jail Break 5K Run for a Cause raises funds for the St. Johns Education Foundation, operating as Investing in Kids (INK!). INK! promotes success for all St. Johns County public school students and teachers through innovative programs.
“The Jail Break 5K is a great way to get moving and help our local schools,” says Dave Chatterton, General Manager of Old Town Trolley Tours®. “Our local teachers and students constantly inspire us, so it’s a great honor to bring the community together in support of education. And we like to create some good-natured competition between the schools with our Jail Break 5K School Team Challenge. The top three schools that have the most registered participants win cash prizes as well as bragging rights throughout the year!”
The Jail Break 5K is a professionally timed and scored point-to-point race. The USATF-certified course begins at the Old Jail, travels down Magnolia Avenue, and across the Vilano Bridge to the Atlantic Ocean. At the finish line, trolleys round up the ‘escaped prisoners’ and shuttle them back to the Old Jail for post-race refreshments, awards, and the Jail Break After Party. All finishers receive a custom finisher's medal and t-shirt (shirt size and availability guaranteed to those registering by Tuesday, September 30th). Placement tiles are awarded to the overall top male and female finishers and the top three finishers in age categories ranging from under 9 to over 75 years. Runners are encouraged to wear their best costumes for the Halloween Costume Contest. A panel of local celebrity judges (judges to be announced soon!) will pick three adult and three youth winners, who will receive cash prizes and the right to strut their stuff at the After Party. St. Johns County Public Schools are invited to show their school spirit by registering students, families, friends, faculty, and staff as a team in the Jail Break 5K School 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 their school. Teams with the second and third-highest numbers of event participants will also receive cash awards.
Pre-race packet pick up is on Friday, October 24th, from 4:30pm to 6:30pm at the Old Town Welcome Center, located at 1305 North Ponce De Leon Blvd. Race day packet pick up and registration is on Saturday, October 25th, from 6:30am to 7:30am at the Old Jail, located at 167 San Marco Ave. The race kicks off at 8am. For more information or to register for the in-person or virtual race, visit the registration page.
ABOUT OLD TOWN TROLLEY TOURS®: Old Town Trolley Tours® of St. Augustine is a full-service tour operator that helps visitors make the most of their St. Augustine vacation. The Trolley Tours experience offers hop-on and hop-off transportation, live narrated tours, entry to world-famous attractions, easy access to over 100 points of interest, and more. Part of Historic Tours of America®, Old Town Trolley Tours® operates in nine cities. Photos to accompany this press release may be found here. Learn more at trolleytours.com/st-augustine and follow along on Facebook and Instagram.
