Nearly 900 participants & $40K raised at the annual 5K hosted by INK! & Old Town Trolley Tours
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 INK! and programs that support public school students and teachers in St. Johns County. This year’s race was one for the record books, as it welcomed nearly 900 participants and raised just under $40,000!
9th Annual Jail Break Hits Record Participation
“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.”
Race Proceeds Support Innovative Programs & Resources for Local Public Schools
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.
Plans for the 10th Annual Jail Break Already Underway
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 after-party 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!”
Thanks to our Jail Break 5K Sponsors and Participants for Making this Year’s Escape Possible!
We’re breaking out the gratitude for our incredible partners for making the Jail Break 5K possible! Thanks to their generous support and to our Jail Breakers, INK!’s programs can continue supporting students and teachers across St. Johns County.





