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  • Stephen Pigman

    Stephen Pigman is St. Augustine’s exceptionally talented one-man-band, incorporating beatboxing, bass, percussion, and vocal harmonies into a barrage of satisfying, toe-tapping sound.

  • Colonial Oak Country Night! Featuring Southern Chaos

    Curated by St. Augustine Country/Western aficionado Davis Loose (of ‘Davis Loose & the Loose Cannons’) in collaboration with WQIK – the Colonial Oak is proud to present a hand-selected variety of acts bringing the best to North Florida’s Country Music […]

  • Sweetwater Imperial 420 IPA Launch Party w/Gentleman’s Crow

    Join us at the Colonial Oak Music Park as we team up with Sweetwater Brewing Company to officially launch their new Imperial 420 IPA! Free Sweetwater swag along with free live music from St. Augustine’s own Gentleman’s Crow! Gentleman’s Crow […]

  • Kyra Livingston Duo

    An exceptional and vocally driven performer, St. Augustine’s Kyra Livingston blends pop, rock, jazz, soul, blues, and funk into a delectable cascade of musical glory.

  • First Coast Comedy Improv (Ticketed Event)

    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. Join us outdoors at St. Augustine’s most unique venue – The Colonial Oak […]

  • Country Night at the Oak! Featuring The Morrow Family Band & Seth Cole

    Curated by St. Augustine Country/Western aficionado Davis Loose  in collaboration with WQIK – the Colonial Oak is proud to present a hand-selected variety of acts bringing the best to North Florida’s Country Music scene. Local to St. Augustine, Florida, The […]

  • STArt Now Narrow Showcase

    STArt Now & Narrow; Northeast Florida’s Premiere Independent Music Magazine – choose unique and intriguing music acts to feature amid the setting of the great Colonial Oak.

  • JAHMEN

    Jacksonville’s JAHMEN  spread a message of unity mixed with the powerful and mighty sounds of reggae music. With a heavy dub influence and a sound true to the roots, you will find great pleasure supporting these mighty men of JAH. […]

  • Bergie! And Jess Cantley

    From the artists Bandcamp page: “‘Bergie!’ spins tales of nostalgic melancholia, and of hope for a brighter future — driven by infectious, psychedelic basslines — to keep you dancing through the darkness and let you know that everything’s gonna be […]

  • First Coast Comedy Improv (Ticketed Event)

    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. Join us outdoors at St. Augustine’s most unique venue – The Colonial Oak […]

  • Country Night at the Oak! Featuring Davis Loose and Chris Canyon

    Curated by St. Augustine Country/Western aficionado Davis Loose  in collaboration with WQIK – the Colonial Oak is proud to present a hand-selected variety of acts bringing the best to North Florida’s Country Music scene. Chris Canyon is  a singer/songwriter as […]

  • Christian Powers

    St. Augustine, Florida native, Christian Powers is a singer/songwriter with a musical style steeped in americana folk pop that reflects his passion for the ocean and wholesome living.