Calendar of Events
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Improv Comedy Night – June 28
Improv Comedy Night – June 28
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 ...
1 event,
Playin’ Possum – June 29
Playin’ Possum – June 29
Playin’ Possum returns to the Oak on June 29 7-10 PM Free admission Family friendly
1 event,
Bad Dog Mama – June 30
Bad Dog Mama – June 30
Bad Dog Mama hits the Oak stage on June 30! 7-10 PM Free admission Family friendly
2 events,
OakFest! July 1 – 4th
Join us under the Oak for our Annual OakFest Celebration where we will celebrate the 7 year anniversary of the Colonial Oak Music Park. This concert series is free to the public and begins on Saturday, July 1! Saturday, July 1 Kick-off! Sililoquy 3-6 PM Circus 7-10 PM Sunday, July 2 Davis Cook 3-6 PM Adam & The Testifiers 7-10 ...
Ramona & The Riot! – July 1
Ramona & The Riot! – July 1
 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 ...
2 events,
Adam & The Testifiers – July 2
Adam & The Testifiers – July 2
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, ...
2 events,
2 events,
OAKfFest with Chillula – 4th of July!
OAKfFest with Chillula – 4th of July!
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 ...
1 event,
Improv Comedy Night – July 5
Improv Comedy Night – July 5
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 ...
1 event,
Rio Grande Band – July 6
Rio Grande Band – July 6
Rio Grande hits the Oak stage for Country Night! 7-10 PM Free Admission Family Friendly
1 event,
I Vibes – July 7
I Vibes – July 7
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.
1 event,
Jake Bradley Band – July 8
Jake Bradley Band – July 8
Catch the Jake Bradley Band at the Oak! 7-10 PM Free Admission Family Friendly
1 event,
Bad Dog Mama – July 9
Bad Dog Mama – July 9
Sunday music at the Oak brought to you by Bad Dog Mama! 2-5 PM Free Admission Family Friendly
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1 event,
Improv Comedy Night – July 12
Improv Comedy Night – July 12
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 ...
1 event,
Tabasco Brothers – July 13
Tabasco Brothers – July 13
The Tabasco Brothers hit the Oak stage for Country Night! 7-10 PM Free Admission Family Friendly
1 event,
Groove Coalition – July 14
Groove Coalition – July 14
The Groove Coalition heads to the the Oak on Friday, July 14! 7-10 PM Free Admission Family Friendly
1 event,
Baba Caiman – July 15
Baba Caiman – July 15
Latin Fusion Band Baba Caiman hits the stage at the Oak! 7-10 PM Free Admission Family & Pet friendly!
1 event,
Jen Howard – July 16
Jen Howard – July 16
Sunday afternoon music at the Oak featuring Jen Howard 2-5 PM Free Admission Family & Pet friendly!
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Improv Comedy Night – July 19
Improv Comedy Night – July 19
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 ...
1 event,
Six Pack Sam – July 20
Six Pack Sam – July 20
Six Pack Sam hits the Oak stage for Country Night! 7-10 PM Free Admission Family Friendly
1 event,
Versvtile – July 21
Versvtile – July 21
Check out Versvtile at the Oak on July 21! 7-10 PM Free Admission Family Friendly Versvtile is a Hard Rock band based out of St. Augustine, FL that plays the styles of Rock, Country, Pop
1 event,
Vange Durst – July 22
Vange Durst – July 22
Vange Durst takes the Oak stage on July 22 7-10 PM Free Admission Family Friendly
1 event,
JT & Alanis – July 23
JT & Alanis – July 23
Catch JT and Alanis at the Oak on Sunday afternoon from 2-5 PM Free admission Family friendly
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1 event,
Improv Comedy Night – July 26
Improv Comedy Night – July 26
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 ...
1 event,
Josh Ford Country Duo – July 27
Josh Ford Country Duo – July 27
The Josh Ford Country Duo hits the Oak stage for Country Night! 7-10 PM Free Admission Family Friendly
1 event,
Istoria – July 28
Istoria – July 28
Istoria returns to the Oak stage on July 28! 7-10 PM Free admission Family friendly
1 event,
Cumberland – July 29
Cumberland – July 29
Saturday night brings Cumberland Band back to the Oak! 7-10 PM Free admission Family friendly
1 event,
Bad Dog Mama – July 30
Bad Dog Mama – July 30
Bad Dog Mama plays some afternoon music at the Oak from 2-5 PM Free admission Family friendly
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1 event,
Improv Comedy Night – August 2
Improv Comedy Night – August 2
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 ...
1 event,
Six Pack Sam – August 3
Six Pack Sam – August 3
Country Night with Six Pack Sam at the Oak! 7-10 PM Free Admission Family & Pet friendly!
1 event,
Baba Caiman – August 4
Baba Caiman – August 4
Catch latin fusion band, Baba Caiman at the Oak! 7-10 PM Free Admission Family Friendly
1 event,
I-Vibes – August 5
I-Vibes – August 5
Catch island rock/reggae band I-Vibes at the Oak! 7-10 PM Free Admission Family Friendly
1 event,
JT & Alanis – August 6
JT & Alanis – August 6
Sunday music at the Oak brought to you by JT & Alanis 2-5 PM Free Admission Family Friendly
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