• JW Gilmore

    JW Gilmore: toe tapping, finger snapping, hip shakin’, blues, boogie woogie,  jump, swing… You’ll be sure to  dance when this show takes the Colonial Oak Stage!

  • Strangerwolf

    Based in Jacksonville, Florida - Strangerwolf has, over a near decade, built up a following that appreciates the bands unique and ethereal music.  We're happy to welcome their exquisite take […]

  • 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.

  • Country Night At the Oak! Featuring Southern Tide

    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 […]

  • 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.

  • Drifting Roots

    This evening, sponsored by the St. Augustine Distillery, will feature free distillery tastings as well as the tasty sounds of Drifting Roots! Drifting Roots is a reggae band based out […]

  • 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 […]