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 […]

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 […]