Old Town Trolley Tours Celebrates 10 Years of Jail Breaks
ST. AUGUSTINE, Florida (Sept. 21, 2026) – The jailbreakers are making their escape again, and this year they’re celebrating a decade on the run. The Jail Break 5K Run for a Cause returns Saturday, Oct. 24 for its 10th year, sending participants from Old Town Trolley Tours® at 167 San Marco Ave. through Uptown St. Augustine, over the Vilano Bridge to the beach. This race benefits for the St. Johns County Education Foundation, operating as Investing in Kids (INK!), which works to promote success for all St. Johns County public school students and teachers through innovative programs.
“Our goal each year is to create one of the most memorable, unique races around,” says Dave Chatterton, General Manager of Old Town Trolley Tours®. “We broke registration records last year and raised just under $40,000 for our local educators and students. For our 10th anniversary, we’re going to have a lot of fun with this year’s theme and make it bigger than ever. We’re hoping to break records again!”
The Jail Break 5K also has one of Northeast Florida’s most scenic routes. The professionally timed, USATF-certified point-to-point course begins at 8 a.m. at the Old Jail, travels down Magnolia Avenue, and across the Vilano Bridge with views of the Matanzas River and Atlantic Ocean, before finishing on the beach. Along the route, runners may find Deputy Otis in hot pursuit, pirates, live music, photo opportunities, and a few surprises. At the finish line, trolleys round up the ‘escaped prisoners’ and shuttle them back to the Old Jail for post-race refreshments, awards, a costume contest, and the Jail Break After Party.
Races are all about the swag and the Jail Break 5K is known for fun medals, from handcuffs to skeleton keys, and this year’s finishers medals and shirts are better than ever. Placement tiles are awarded to the overall top male and female finishers and the top three in age categories ranging from under 9 to over 80 years. With Halloween just days away, costumes and courses entertainment are half the fun. There is $1,000 in costume prize money up for grabs - $500 for first, $300 for second, and $200 for third - plus prizes for the top three youth costumes.
St. Johns County Public Schools are invited to show their school spirit in the Jail Break 5K School Team Challenge by registering students, families, friends, faculty, and staff as a team. The school with the most registered participants receives a one-of-a-kind trophy, bragging rights, and a $1,000 award, with cash awards for second and third. For more information or to register, visit the registration page.
