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image of dancers on stage, dressed in red & white dance costumes for the St Augustine Winter Spectacular 2021
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St. Augustine Winter Spectacular 2025

Lewis Auditorium at Flagler College 14 Granada Street, St. Augustine

St. Augustine Winter Spectacular 2025 You're sure to get in the Holiday spirit at the St. Augustine Winter Spectacular at Lewis Auditorium!  This popular family-friendly, entertaining holiday production follows a young girl’s journey home for the holidays. Expect high-kick dancers reminiscent of the iconic Radio City Rockettes, mixed with Holiday music, ballerinas, acrobats, actors, and [...]

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Music at Colonial Oak Music Park
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Music at Colonial Oak Music Park

Colonial Oak Music Park 33 St George St., St. Augustine

While you're in downtown St. Augustine in December, stop in and listen to the Music at Colonial Oak Music Park.  You'll hear anything from country to blues to funk to folk to rock 'n roll. Free Admission for most events — with the exception of ticketed events. Family-friendly. 7:00pm-10:00pm — Thursday, Friday, and Saturday nights [...]

Most are Free

Performances of Annie at Limelight
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Performances of Annie at Limelight

Limelight Theatre 11 Old Mission Avenue, St. Augustine

Performances of the beloved musical Annie are at Limelight Theatre December 5-21, 2025. About Annie Book by Thomas Meehan Music by Charles Strouse Lyrics by Martin Charnin Original Broadway Production by Martin Charnin Directed by Jonny O'Leary The musical is about Annie - an optimistic orphan who captures hearts (and maybe even saves a billionaire). [...]

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Jon Pardi The Christmas Show
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Jon Pardi The Christmas Show

St. Augustine Amphitheatre 1340C A1A South, St. Augustine

Jon Pardi is bringing The Christmas Show to the St. Augustine Amphitheatre ... Friday and Saturday, December 12 & 13, 2025. It’s been more than a decade since Capitol Records Nashville artist Jon Pardi began careening down the highway.  And, he's been leading the charge to modernize honky tonk with roaring guitars and a roaring, [...]

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Shaun Cassidy at PV Concert Hall

Shaun Cassidy at PV Concert Hall

Ponte Vedra Concert Hall 1050 A1A North, Ponte Vedra Beach

Shaun Cassidy is appearing at the Ponte Vedra Concert Hall as part of his The Road to Us Tour on Saturday, December 13, 2025.   An American writer, producer, actor, and singer - he's the son of Tony award winning actor Jack Cassidy and Academy award winner Shirley Jones.  And, he's the half-brother of the late [...]

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Holiday Hootenanny Improv Comedy Show
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Holiday Hootenanny Improv Comedy Show

Third Space Improv 200 Malaga Street, #7, St. Augustine

☃️ Get ready for a festive night of laughter and surprises during The Holiday Hootenanny Improv Comedy Show!  The show brings together quick-witted performers for a wild and wacky celebration of the season.  From holiday-themed games to spontaneous scenes inspired by audience suggestions, this show is packed with cheer, comedy, and a dash of chaos. [...]

$15.00 – $20.00

A Very Grinchy Comedy Show
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A Very Grinchy Comedy Show

Third Space Improv 200 Malaga Street, #7, St. Augustine

A Very Grinchy Comedy Show Tis the season… for sauce, silliness, and a little holiday chaos! A Very Grinchy Comedy Show brings together some of the funniest comics in Northeast Florida for a night of sharp wit and unapologetically naughty cheer. Forget the sugarplums—this lineup serves up laughs for anyone whose holiday spirit comes with [...]

$17.00 – $20.00