Proceeds from the Jail Break 5K benefit Investing in Kids (INK!) . Our mission: To provide innovative programs, teacher support, and classroom resources to promote success for all St. Johns County public school students and teachers. WHEN Saturday, October 24, 2026 - 8:00 AM WHERE The Old Jail 167 San Marco Avenue St. Augustine, FL 32084 ENTRY FEES Until May 31 = $25 (Special pricing!) June 1 - July 31 = $30 August 1 - October 16 = $35 October 17 - October 23 = $40 Race Day - October 24 =$45 VIRTUAL ONLY = $40 VIRTUAL RACE Can't #ESCAPE with us on October 25? Make your escape virtually! Sign up for the Jail Break 5K VIRTUAL option and submit your results to RunSignUp. You can pick up your JB5K race swag on October 23rd at Packet Pick Up or we will ship your swag to you after the race. There will be no awards for the virtual race. SCHEDULE OF EVENTS Pre-Race Packet Pick Up/Registration: Friday, Oct. 23, 2026, 4:30 - 6:30 PM Old Town Welcome Center , 1305 North Ponce De Leon Blvd. St. Au
Hotels Near This Race
Find accommodation close to the start line in Saint Augustine, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
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Race Travel Insurance
Don't forget travel insurance for October 24.
You've trained for months and booked a trip to Saint Augustine, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
