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 […]

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.

The Oak is always happy to welcome Baba Caiman – Florida's premiere Latin Fusion band! Having influences from different parts of Latin America (El Salvador, Colombia, and USA), Baba Caiman focuses […]

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.

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 […]

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 […]

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!

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 […]

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.

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 […]