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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.

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Events

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  • Hot Diggity Dog Day

    Hot Diggity Dog Day

    Featured
    St. Augustine Humane Society 1665 Old Moultrie Road, St. Augustine, FL, United States

    4th Annual Hot Diggity Dog Day Stop by the St. Augustine Humane Society for their 4th annual Hot Diggity Dog Day.  Fun for everyone, whether you have two legs or four! When: Saturday, April 25, 2026 -- 10:00am-2:00pm Admission is free and everyone is invited!  And ... Free microchip vouchers for the first 50 attendees! There's a [...]

    Free

  • caricature image of skull with Jail Break in one eye socket, 5K in other eye socket

    Jail Break 5K 2026

    Featured
    Old Jail 167 San Marco Avenue, St. Augustine, FL, United States

    Jail Break 5K 2026 & Halloween Costume Contest All runners and walkers are welcome to participate in the 10th Annual Jail Break 5K.  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. When: Saturday, October 24, 2026 -- 8:00am Course Info [...]

    Prices Vary

  • Holly Jolly Shopping Spree

    2026 Holly Jolly Shopping Spree

    The Spice & Tea Exchange 167 San Marco, St. Augstine, FL, United States

    2026 Holly Jolly Shopping Spree Mark your calendars for the annual Holly Jolly Shopping Spree!  Do some Holiday shopping for a good cause ... this community fundraiser benefits a local charity.  Shop local and receive special discounts and offers from Uptown merchants.  Along the way stop for a tasty brunch!  And, be sure to capture [...]

    $70.00