St. Augustine, the nation’s oldest city, also holds the distinction of being one of the nation’s most charming. Whether you’re a longtime resident or visiting the area for the first time, we’ve gathered all the resources you need to find where to stay, what to do and other community information about our unique little village.
Jail Break 5K 2025 & Halloween Costume Contest All runners and walkers are welcome to participate in the annual Jail Break 5K - Saturday, October 25, 2025 -- 8:00am. During the race, the traditional Jail Break 5K Halloween Costume Contest will take place. Run/walk in costume to win one of the cash prizes. Course Info [...]
2025 Holly Jolly Shopping Spree Mark your calendars for the 15th annual Holly Jolly Shopping Spree! Shop for a good cause ... this community fundraiser benefits a local charity. Do some Holiday shopping -- shop Local and receive special discounts and offers from Uptown merchants. And, you'll also enjoy a trolley ride along with brunch! [...]