9th Annual Jail Break 5K Run!

Every October in the nation’s oldest city, runners and walkers gear up for Old Town Trolley Tour’s Jail Break 5K.  This popular event is a Halloween-themed escape race that blends historic architecture, seaside views and spirited charity fun. The event begins at the Old Jail Museum and winds its way through downtown, over the Vilano Bridge, ending near the Atlantic Ocean.

The race is open to all abilities and encourages participants to dress in costume—especially pirates, ghosts or jail-break-themed attire. Packet pickup takes place the day before at the Old Town Welcome Center on North Ponce De Leon Blvd.  Post-race festivities and an after-party will be held at the Old Jail Museum property.

The event is more than just a race—it’s a fundraiser for public education. Proceeds support Investing in Kids (INK!), a local initiative that provides classroom resources and teacher support across St. Johns County public schools.

Participants in past years describe the route as scenic and festive.  Runners launch from the Romanesque-Revival style Old Jail, passing Magnolia Avenue’s historic storefronts, crossing the Vilano Bridge with views of the water, and finishing along the beach. Whether you’re sprinting or strolling in a costume, the vibe is community-driven, family-friendly and slightly spooky.

Costumes are highly encouraged, and the event features a dedicated costume contest—with cash prizes for adults and youth categories. Awards are also given for top finishers across age groups.  Virtual participation is available for those who can’t make it on race day.