Investing in Kids (INK!) and Old Town Trolley Tours of St. Augustine to hold Annual Jail Break 5K fundraiser, Oct. 22

Jail Break 5K 2022

St. Augustine, Fla. – August 10, 2022 – Investing in Kids (INK!) and Old Town Trolley Tours of St. Augustine have announced this year’s Annual Jail Break 5K run and walk fundraiser. The event will be held on Saturday, October 22, beginning at the Old Jail Museum, 167 San Marco Blvd. in St. Augustine, Fla., with race start at 7:30 a.m.

This family friendly event includes adult and children “jail breakers” who plan their escape from the 130-year-old historic venue and run through picturesque, historic areas of St. Augustine also known as The Nation’s Oldest City. Scenic ocean, river and Intracoastal Waterway views are featured in the run over the Francis and Mary Usina “Vilano” Bridge, and wrap up at Vilano Beach Pavilion, 20 Vilano Road in St. Augustine. The event is a 5K USA Track & Field (USATF) Certified Course # FL17069TY.

New this year is a team challenge for St. Johns County School District students, families, friends, faculty, and staff. The school with the highest number of registered participants will receive a one-of-a kind Jail Break 5K Team Challenge trophy, award accolades, and a $1,000 award. Prize money will also be awarded to the second and third place school teams registering with the second and third highest number of event participants.

Festivities will also feature entertainment and activities for runners and attendees, and a pre-race warm up at the Old Jail Museum. All runners will be rounded-up as “prisoners” as they begin the race and will be transported back to the Old Jail from the finish line at Vilano Beach by shuttle.

A Halloween costume contest sponsored by Ghosts and Gravestones and decided by a panel of local celebrity judges will include $1,000 in cash prizes. Runners and walkers are encouraged to participate while wearing a costume to be considered for one of three awards for best costume. Unique race t-shirts are guaranteed to those who register by Saturday, October 1.

Early race registration runs through Wednesday, August 31 and cost is $30 for each participant. From Thursday, September 1 until Friday, September 30, cost is $35 per each participant. From Saturday, October 1 until Friday, October 21, cost is $40 per each participant. Day of race entries on October 22 are $45 per participant. The first 700 race finishers will receive this year’s distinctive skeleton key medal.

Visit to register online.

Overall male and female finishers and the top three runners will be in the following age groups: 9 and under, 10-14, 15-19, 20-24, 25-29, 30-34, 35-39, 40-44, 45-49, 50-54,  55-59, 60-64, 65-69, 70-74, and 75 and older. Water stations will be located at the race start, and at the one-mile mark, two-mile mark, and finish line. Free race parking is available at Old Town Trolley locations including 167 San Marco Ave. and 1305 N. Ponce De Leon Blvd. The preferred hotel partner for Jail Break 5K is The Sebastian Hotel, located at 333 S. Ponce de Leon Blvd., St. Augustine, Fla. Reservations can be made by contacting the hotel at (904) 209-5580.

Proceeds from the race benefit The St. Johns County Education Foundation, Inc., a 501(c)3 education foundation, which operates as Investing in Kids (INK!). INK! promotes academic success for all St. Johns County public school students by providing innovative programs, teacher support and classroom resources to benefit over 50,000 students and approximately 3,000 teachers.

Old Jail Museum is an integral part of St. Augustine’s rich heritage and features unique personalities as important roles for Historic Tours of America and Old Town Trolley Tours. Trolleys, shuttle transportation and entertainment stops are featured throughout historic St. Augustine for visitors and residents offering 22 stops with more than 100 points of interest. The trolleys are eco-friendly and noise sensitive to the surroundings and neighborhoods around the City. For more information, visit or call 904-829-3800.