The Jail Break 5k


Jail Break 5k Escape From St. Augustine

The Old Town Trolley Tours proudly announce the Jail Break 5k.  Make your escape from the Authentic Old Jail to the Atlantic Ocean! Costumes encouraged, full trolley system for spectators and participants, huge costume party and bicycle rodeo after the race! Bring the family for an opportunity like no other in the historic City of St. Augustine. All registrants receive a sought after Velo Fest T Shirt, post race beverage and snacks, certified USATF 5k, handcuffs, we mean finisher medal, and FUN. Can you make it before they catch you?

History of the Old Jail: Home to prisoners for over 60 years, the Old Jail in St. Augustine looks more like a resort than a maximum-security facility. The original structure was built in 1891 by Henry Flagler; and although it has been restored and renovated throughout the years, it looks very much the way it did when it opened over a century ago.

Our luxurious Victorian style rooms are a perfect way to rest after running in a race like The Jail Break 5k.  In our beautiful Emerald room treat yourself to a soak in the jet Jacuzzi tub complete with a large double rain head walk in shower with body sprays.  Wake up and enjoy our chef’s choice hot breakfast with coffee and juice served table side every morning.  Our onsite parking and excellent location to historic downtown St. Augustine make seeing your favorite sites a breeze.  Each room is decorated and named after a precious gemstone making Carriage Way Bed & Breakfast the Jewel of the Ancient City.