Jail Break 5k Raised $40k for Local Students + Teachers
ST. AUGUSTINE, Florida (November 10, 2025)—Investing in Kids (INK!) and Old Town Trolley Tours® hosted the 9th Annual Jail Break 5K at The Old Jail on Saturday, October 25th. The race began at The Old Jail and ended in downtown Vilano Beach. The event raises funds for the St. Johns County Education Foundation, Inc., which operates as INK!, and supports public school students and teachers. And this year’s race was one for the record books, as it welcomed nearly 900 participants and raised just under $40,000.
“We’re thrilled to say that this was the most well-attended race so far,” said Cathy Newman, INK!’s Executive Director. “We had a goal of 850 participants, but 879 runners, walkers, and virtual athletes registered to participate. With next year marking the 10th anniversary of the Jail Break 5K, we’re aiming for 1,000 competitors, but we’d love to surpass that goal as well! We’re so thankful for the partnership with Old Town Trolley Tours® – from the custom finisher medals to the Old Jail Cast in character to the huge afterparty and costume contest on the course, it makes the day an absolute blast.”
The annual Jail Break 5K is a longstanding community fundraiser for INK!. This year, the race raised just under $40,000 in gross proceeds. The funds are used to support students and teachers in the St. Johns County public school system by providing innovative programs and classroom resources to close the literacy gap, improve graduation rates, and ensure that all students reach their full potential. INK!’s programs include Tools 4 Schools, Take Stock in Children, Five Year Learning (FLY), Teacher of the Year, scholarship stewardship, and more. Schools also had the opportunity to win additional grant funds by participating in the Jail Break 5K School Team Challenge. The public school with the highest number of registered participants received a one-of-a-kind Jail Break 5K School Team Challenge trophy, bragging rights, and a $1,000 grant for their school. Taking first place was the St. Augustine Public Montessori School, while Lakeside Academy came in second, winning a $500 grant, and St. Johns Virtual School came in third, winning a $250 grant. The Ancient City Road Runners claimed the Community Team Challenge Title, with 32 members participating in the race.
INK! and Old Town Trolley Tours are already planning next year’s race, scheduled to take place on Saturday, October 24, 2026. “We can’t give away too many details about next year’s race,” smiles Dave Chatterton, General Manager of Old Town Trolley Tours®. “We plan to add more fun, more entertainment, have an amazing new medal design, and make the course and afterparty even better than the previous year – but we want our Jail Breakers to be surprised. After all, we’ll be celebrating 10 years of escaping The Old Jail!”
ABOUT INVESTING IN KIDS: The St. Johns County Education Foundation, Inc., which operates as Investing in Kids (INK!), promotes success for all St. Johns County public school students and teachers by providing innovative programs, teacher support, classroom resources, and scholarships to benefit more than 52,000 students and approximately 3,200 teachers. INK! is a 501(c)3 education foundation with offices at 1 Christopher Street in St. Augustine. Photos to accompany this release may be found here. Learn more at ink-stjohns.org and follow along on Facebook @InvestingInKids and Instagram @INK_InvestingInKids
