Don’t miss Ramona & The Riot on July 1st at the Oak! 7-10 PM Free Admission Family Friendly A coming together of hip-hop, rhythm and blues, funk, pop, rock, and soul, Ramona is a musical treasure trove of long lost one-hit-wonders and modern contemporary favorites. Ramona + the Riot is accoladed as St. Augustine’s number one award winning cover song ...

Adam & The Testifiers return to the Oak on July 2! 7-10 PM Free Admission Family Friendly   Adam is a singer, drummer, and composer based out of Atlanta, GA. Throughout his 10-year career as a professional drummer, he has worked with artists such as Joe Gransden, the Bill Peterson Trio, Fred Wesley, Katie Skene, the Brown Goose, Kat Hall, ...

Look no further for the best 4th of July party in Downtown St. Augustine, OAKFest 2024! Come celebrate with Chillula under the Oak starting at 7PM. Conveniently located across from the Castillo de San Marcos — take a break from the tunes at 9:30PM watch “The Fireworks Over The Matanzas” Free show Family friendly   Chillula is a dance band ...

Your 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. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean and never mean! Pay-What-You-Will. All ...

Rio Grande hits the Oak stage for Country Night! 7-10 PM Free Admission Family Friendly

I-Vibes returns to the Oak on July 7! 7-10 PM Free Admission   For the past 8 years, I-Vibes has been pushing love & positivity through their music in NE Florida. The band has toured and performed locally with some of the biggest names in the reggae genre, including Grammy Award nominees SOJA and Morgan Heritage.

Catch the Jake Bradley Band at the Oak! 7-10 PM Free Admission Family Friendly

Sunday music at the Oak brought to you by Bad Dog Mama! 2-5 PM Free Admission Family Friendly

Your 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. And it gets better! This show is for everyone! You can bring the whole family because these improvisers play smart… to ensure the show is always clean and never mean! Pay-What-You-Will. All ...