• Sing Out Loud Local Showcase: September 12 – 14

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    The Local Artist Showcases are a cornerstone of the Sing Out Loud Festival experience, offering music fans an opportunity to explore Northeast Florida’s diverse and vibrant music scene. From indie rock and bluegrass to hip hop, country, spoken word and comedy, the lineup reflects the richness of talent found throughout the region.   Free, all […]

    free
  • Improv Comedy Night – September 17

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Your First Coast Comedy veteran professionals have no plan and willingly dive headfirst into almost any challenge the audience will throw at them, resulting in unforgettably hilarious moments. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean […]

    pay-what-you-will
  • Sing Out Loud Local Showcase: September 18-21

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    The Local Artist Showcases are a cornerstone of the Sing Out Loud Festival experience, offering music fans an opportunity to explore Northeast Florida’s diverse and vibrant music scene. From indie rock and bluegrass to hip hop, country, spoken word and comedy, the lineup reflects the richness of talent found throughout the region. Free, all ages, […]

    free
  • Improv Comedy Night – September 24

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Your First Coast Comedy veteran professionals have no plan and willingly dive headfirst into almost any challenge the audience will throw at them, resulting in unforgettably hilarious moments. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean […]

    pay-what-you-will
  • Country Night w/ Josh Tennessee Worthy Ensemble & Dewey Via – September 25

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with us and the Josh Tennessee Worthy Ensemble with special guest, Dewey Via! 7-10 PM FREE Fun for all ages Friendly pups welcome Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more! On […]

    free
  • St. Augustine Songwriters Festival – September 26 – 28

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    The St. Augustine Songwriters Festival offers music lovers an intimate look into the creative processes and inspiring stories behind the hits penned by some of the music industry’s leading songwriters. This FREE annual event is not to be missed!   Friday, September 26 2:00PM – 2:50PM: Lost Saints 3:00PM – 4:30PM: Mark Irwin, AJ Kross, […]

    free
  • Country Night w/ Cam Wheaton – October 2

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with Cam Wheaton!  7-10 PM FREE Fun for all ages Friendly pups welcome Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more! On site dining from St. Augustine Seafood Company! Click here for Instagram! […]

    free
  • Dogtoberfest w/ Circus – October 3

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Dogtoberfest returns to the Oak on Friday, October 3rd benefiting Ayla’s Acres No Kill Animal Shelter! Bring your pups out for a doggie costume contest, raffles, and a rockin’ performance by eclectic electric classic rock band, Circus! Free Admission7-10 PMSee You at the Oak!

    free
  • Closed for Private Event – October 4

    Colonial Oak Music Park 21 St George Street, St Augustine, FL, United States

    Closed for Private Event! Get information about booking your own special event at the Oak here!