Kyra Livingston – June 25
2023-06-25 14:00 - 17:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Enjoy Sunday afternoon music at the Oak by Kyra Livingston
2-5 PM
Free Admission
Family Friendly

Improv Comedy Night – June 28
2023-06-28 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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 seating is General Admission.

No ticket is better than any other. Just pay what you think the experience is worth.

Playin’ Possum – June 29
2023-06-29 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Playin’ Possum returns to the Oak on June 29
7-10 PM
Free admission
Family friendly

Bad Dog Mama – June 30
2023-06-30 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Bad Dog Mama hits the Oak stage on June 30!
7-10 PM
Free admission
Family friendly

OakFest! July 1 – 4th
2023-07-01 15:00 - 2023-07-04 23:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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 PM

Monday, July 3

Bret Blackshear 3-6 PM
Dewey Via Band 7-10 PM

Tuesday, July 4

Branden Parrish 3-6 PM
Chillula 8-11 PM

Ramona & The Riot! – July 1
2023-07-01 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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 ensemble, and packs a heavy punch onstage with internationally recognized original music. Featured by Best of NPR Music in 2016, and again with their 2020 original release “Blood & Sand” and performing in various capacities from duo, trio, to a righteously powerful full band setting.

Adam & The Testifiers – July 2
2023-07-02 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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, the Steve Gilmore Quartet, the Blues Factor Band, Brittany Howard, Duane Betts, and George Clinton. He has had the opportunity to open for artists such as the Revivalists, the Nth Power, and KRS-1 and to play festivals such as Suwannee Hulaween, Savannah Music Festival, and New Orleans Jazz Fest.
After 7 years of Adam’s first band out of Tallahassee, FL: Urban Soul, the group of funksters decided it was time to say goodbye to the band and birth a new project. Urban Soul at this point is no longer your typical band; we’re a collective of hidden talent and deep pocket that lies amongst the entire southeastern region. We run our ship less like the Meters or the Beatles and more like the Funk Brothers or the Wrecking Crew. The new funk collective would be named The Testifiers in 2020. Check out our upcoming album “Chapter Book” and subscribe to our mailing list for a free download of our previous EP “Variety.”

TBA – July 3
2023-07-03 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

OAKfFest with Chillula – 4th of July!
2023-07-04 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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 based out of St Augustine, Florida. We specialize in festivals, weddings, private events, and playing in clubs or bars. Chillula blends the styles of R&B, Funk, Hip- Hop, Soul, Rock, Reggae, & Jazz into a sound that everyone can groove to and is sure to fill the dance floor.

Improv Comedy Night – July 5
2023-07-05 19:30 - 21:00

Rio Grande Band – July 6
2023-07-06 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Rio Grande hits the Oak stage for Country Night!
7-10 PM
Free Admission
Family Friendly

I Vibes – July 7
2023-07-07 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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.

Jake Bradley Band – July 8
2023-07-08 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Catch the Jake Bradley Band at the Oak!
7-10 PM
Free Admission
Family Friendly

Bad Dog Mama – July 9
2023-07-09 14:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Sunday music at the Oak brought to you by Bad Dog Mama!
2-5 PM
Free Admission
Family Friendly

Improv Comedy Night – July 12
2023-07-12 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Tabasco Brothers – July 13
2023-07-13 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Tabasco Brothers hit the Oak stage for Country Night!
7-10 PM
Free Admission
Family Friendly

Groove Coalition – July 14
2023-07-14 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Groove Coalition heads to the the Oak on Friday, July 14!

7-10 PM
Free Admission
Family Friendly

Baba Caiman – July 15
2023-07-15 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Latin Fusion Band Baba Caiman hits the stage at the Oak!
7-10 PM
Free Admission
Family & Pet friendly!

Jen Howard – July 16
2023-07-16 14:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Sunday afternoon music at the Oak featuring Jen Howard
2-5 PM
Free Admission
Family & Pet friendly!

Improv Comedy Night – July 19
2023-07-19 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Six Pack Sam – July 20
2023-07-20 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Six Pack Sam hits the Oak stage for Country Night!
7-10 PM
Free Admission
Family Friendly

Versvtile – July 21
2023-07-21 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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

Vange Durst – July 22
2023-07-22 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Vange Durst takes the Oak stage on July 22

7-10 PM
Free Admission
Family Friendly

JT & Alanis – July 23
2023-07-23 14:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Catch JT and Alanis at the Oak on Sunday afternoon from 2-5 PM

Free admission
Family friendly

Improv Comedy Night – July 26
2023-07-26 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Josh Ford Country Duo – July 27
2023-07-27 19:00 - 22:00 | Colonial Quarter
The Josh Ford Country Duo hits the Oak stage for Country Night!
7-10 PM
Free Admission
Family Friendly

Istoria – July 28
2023-07-28 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Istoria returns to the Oak stage on July 28!
7-10 PM
Free admission
Family friendly

Cumberland – July 29
2023-07-29 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Saturday night brings Cumberland Band back to the Oak!
7-10 PM
Free admission
Family friendly

Bad Dog Mama – July 30
2023-07-30 14:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Bad Dog Mama plays some afternoon music at the Oak from 2-5 PM
Free admission
Family friendly

Improv Comedy Night – August 2
2023-08-02 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
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 seating is General Admission.

No ticket is better than any other. Just pay what you think the experience is worth
