Colonial Quarter

Closed for Private Event – October 4
2025-10-04 08:00 - 17:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Closed for Private Event!
Get information about booking your own special event at the Oak here!

Dogtoberfest w/ Circus – October 3
2025-10-03 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Dogtoberfest returns to the Oak on Friday, October 3rd benefiting Ayla’s Acres No Kill Animal Shelter!
Bring your pups out for a doggie costume contest, raffles, and a rockin’ performance by eclectic electric classic rock band, Circus!
Free Admission7-10 PMSee You at the Oak!

Country Night w/ Cam Wheaton – October 2
2025-10-02 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with Cam Wheaton!

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

St. Augustine Songwriters Festival – September 26 – 28
2025-09-26 14:00 - 2025-09-28 18:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The St. Augustine Songwriters Festival offers music lovers an intimate look into the creative processes and inspiring stories behind the hits penned by some of the music industry’s leading songwriters. This FREE annual event is not to be missed!

Friday, September 26
2:00PM – 2:50PM: Lost Saints
3:00PM – 4:30PM: Mark Irwin, AJ Kross, Davis Loose
4:40 PM – 6:10PM: Nick Norman, Adam Wood, David Tolliver
6:20PM – 7:50PM: Gretchen Peters, Frank Myers, Jenny Tolman
8:00PM – 9:30PM: McCoy Moore, Johnny Clawson, Brian Davis
9:35PM: Rodney Clawson, Monty Criswell
Saturday, September 27
2:00PM – 2:50PM: Justin Morgan, Braden Jameson
3:00PM – 4:30PM: Emmet Stevens Jr, Murphy Elmore, Davis Cook
4:40 PM – 6:10PM: Jesse Rice, Lost Saints, Emily Landis
6:20PM – 6:55PM: Cliff Cody (Shipwreck Album Release)
7:00PM – 8:30PM: Justin Wilson, Jim McCormick, Chad Warrix
8:40PM – 10:00PM: Jon Nite, Brock Berryhill
Sunday, September 28
11:30AM – 11:55PM: Davis Cook
12:00PM – 2:00PM: McCoy Moore, Brian Davis, Murphy Elmore, Dave Brainard
2:10PM – 3:40PM: Adam Wood, Jenny Tolman, Justin Morgan
3:50PM – 5:30PM: Chris Blair, Emmet Stevens Jr, Poor Life Choices

Country Night w/ Josh Tennessee Worthy Ensemble & Dewey Via – September 25
2025-09-25 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with us and the Josh Tennessee Worthy Ensemble with special guest, Dewey Via!

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – September 24
2025-09-24 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

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Sing Out Loud Local Showcase: September 18-21
2025-09-18 19:00 - 2025-09-21 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Local Artist Showcases are a cornerstone of the Sing Out Loud Festival experience, offering music fans an opportunity to explore Northeast Florida’s diverse and vibrant music scene. From indie rock and bluegrass to hip hop, country, spoken word and comedy, the lineup reflects the richness of talent found throughout the region.
Free, all ages, friendly dogs welcome
Thursday, September 18
7:15PM: TBD
Friday, September 19
6:00PM – 7:00PM: SOFT
7:30PM – 8:30PM: American Souvenir
9:00PM – 10:00PM: Intersellar Groove Machine
Saturday, September 20
3:00PM – 4:00PM: Charlie Robertson
4:30PM – 5:30PM: Few Fellas Brass Band
6:00PM – 7:00PM: Billy Buchanan
7:30PM – 8:30PM: Christopher Shawn
9:00PM – 10:00PM: Feverdreams
Sunday, September 21
2:00PM – 3:00PM: (V)OWLS
3:30PM – 4:30PM: Treis and Friends
5:00PM – 6:00PM: The Saltones
6:30PM – 7:30PM: The Rennys
8:00PM – 9:00PM: Souvineer
*Artists, dates, and times are subject to change

Improv Comedy Night – September 17
2025-09-17 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Sing Out Loud Local Showcase: September 12 – 14
2025-09-12 18:00 - 2025-09-14 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Local Artist Showcases are a cornerstone of the Sing Out Loud Festival experience, offering music fans an opportunity to explore Northeast Florida’s diverse and vibrant music scene. From indie rock and bluegrass to hip hop, country, spoken word and comedy, the lineup reflects the richness of talent found throughout the region.

Free, all ages, friendly dogs welcome

Friday, September 12
6:00PM – 7:00PM: Shayla Nelson
7:30PM – 8:30PM: Matt Megrue
9:00PM – 10:00PM: Chemtrails
Saturday, September 13
4:30PM – 5:30PM: The Music Misfits
6:00PM – 7:00PM: Closer to the ocean
7:30PM – 8:30PM: The Currys
9:00PM – 10:00PM: Idle Acres
Sunday, September 14
3:30PM – 4:30PM: Nathan Allen
5:00PM – 6:00PM: Hannah Stokes Band
6:30PM – 7:30PM: Folk Is People
8:00PM – 9:00PM: TBD
*Artists, dates, and times are subject to change

Dewey Via Band – September 11
2025-09-11 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with us and the Dewey Via Band!

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – September 10
2025-09-10 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Sing Out Loud Local Showcase: September 5 – 7
2025-09-05 18:00 - 2025-09-07 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Local Artist Showcases are a cornerstone of the Sing Out Loud Festival experience, offering music fans an opportunity to explore Northeast Florida’s diverse and vibrant music scene. From indie rock and bluegrass to hip hop, country, spoken word and comedy, the lineup reflects the richness of talent found throughout the region.
Free, all ages, friendly dogs welcome
Friday, September 5
6:00PM – 7:00PM: Dizzlephunk
7:30PM – 8:30PM: Tonal
9:00PM – 10:00PM: Armadillo Operator
Saturday, September 6
6:00PM – 7:00PM: Violet Mourning
7:30PM – 8:30PM: DL is OK
9:00PM – 10:00PM: Tori Nance
Sunday, September 7
3:30PM – 4:30PM: The Bridge Street Vibe
5:00PM – 6:00PM: Gavin Powell
6:30PM – 7:30PM: Ashley Estevez
8:00PM – 9:00PM: Allen Arena – Good Time Charlie

*Artists, dates, and times are subject to change

Country Night w/ Cumberland & Friends – September 4
2025-09-04 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with Cumberland & Friends!

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Country Night ARTIST TBA – September 4
2025-09-04 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with us! Artist TBA!

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – September 3
2025-09-03 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Muhly – August 31
2025-08-31 14:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Muhly!

FREE show
2-5 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Versvtile – August 30
2025-08-30 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with VERSVTILE

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Virginia Sweet – August 29
2025-08-29 19:00 - 22:00
Join us at the Oak with Virginia Sweet!

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Country Night w/ Vern Daysel and the Burning Breeze – August 28
2025-08-28 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Vern Daysel and the Burning Breeze!

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – August 27
2025-08-27 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

No Music – August 24
2025-08-24 08:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Halfway to SweetWater Battle of the Bands – August 23
2025-08-23 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Stella Soul – August 22
2025-08-22 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Stella Soul

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Country Night with the Josh Tennessee Worthy Ensemble – August 21
2025-08-21 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy with music by the Josh Tennessee Worthy Ensemble.

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – August 20
2025-08-20 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Zach Deputy (Ticketed show) – August 17
2025-08-17 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Reflecting on his live shows, Zach says “music to me is about bringing people together from all walks of life and living in the moment with a joyful heart!” Deputy’s one man show creates a unique experience straight from the soul every night, raw and uncut with absolutely nothing prerecorded. As a pioneer of looping and synth guitar work well ahead of his time, he’s taken the technology to uncharted lands delivering a pocket groove unique to the ears. Zach says, “call me crazy, but I’ve always believed live music should always be live, but I’ve also always loved a good tranced out dance party too.” With this in mind he tailored his performances to meet his convictions. Combining his family roots Island vibe with his low country southern soul, a pinch of tranced out hippy hop, and a vast amount of talent, Zach’s sound emerges in focus.

Bad Dog Mama – August 16
2025-08-16 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Bad Dog Mama!

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Mojo Hand – August 15
2025-08-15 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Mojo Hand!

FREE show
7-10 PM
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Country Night with the JT Band – August 14
2025-08-14 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy with music by the JT Band.

7-10 PM
FREE
Fun for all ages
Friendly pups welcome
Multiple bars stocked with craft beers, St. Augustine Distillery Products, & more!
On site dining from St. Augustine Seafood Company!

Click here for Instagram!
Click here for Facebook!

Improv Comedy Night – August 13
2025-08-13 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
