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 Music Park. And it gets better! This show is for everyone! You can bring the whole family because these improvisers ...

Colonial Oak Country Night! feat. Gavin Powell/Davis Loose

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 scene. Tonight’s featured artists: -Jacksonville-born Tallahassee resident Gavin Powell, known for surprising listeners with a unique laid-back southern style that ...

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 on traditional sounds to the Colonial Oak Music Park!

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.

Colonial Oak Country Night!

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 scene.

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 of acts bringing the best to North Florida’s Country Music scene. According to Southern Tide’s own statement: “We play southern influenced rock n roll, blues, classic country and Americana music. ...

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 of Central Florida. With music created from brotherly collaboration, the musicians of Drifting Roots spent time in different areas of the country exploring new places and teaching themselves the recording ...

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.