Improv Comedy Night – September 10
2025-09-10 19:30 - 21:00 UTC | 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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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!
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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

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 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 24
2025-09-24 19:30 - 21:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

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!

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/ 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!

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!

Closed for Private Event – October 4
2025-10-04 08:00 - 17:00 | 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!

No Music – October 5
2025-10-05 08:00 - 17:00
No music today!

Country Night w/ Cade and the Palmetto Kickers – October 9
2025-10-09 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 Cade and the Palmetto Kickers!

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!

Tangled Orchid – October 10
2025-10-10 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Tangled Orchid! A dynamic live rock band dedicated to delivering unforgettable performances that span multiple genres and eras, covering iconic songs from the 1960s to the present day.

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!

Baba Caiman – October 11
2025-10-11 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Latin Fusion favorite, Baba Caiman!

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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!

No Music – October 12
2025-10-12 11:00 - 19:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Dave Matthews Tribute Band (TICKETED) – October 15
2025-10-15 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
For over 20 years, the Dave Matthews Tribute Band has been performing sold out shows around the world; playing over 2,000 concerts in 46 states and 9 countries. Throughout the years, the band has evolved from a bar hopping cover band into a dedicated and true tribute band with one goal; to recreate the classic Dave Matthews Band sound so many of us know and love.

TICKETS AND MORE INFO HERE!

Polyrhythmics (Ticketed Show) – October 16
2025-10-16 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
POLYRHYTHMICS “LIFE FROM BELOW” live at the Colonial Oak Music Park on October 16

Get your tickets and more info here!

Halfway to SweetWater Music Festival – October 17-19
2025-10-17 16:00 - 2025-10-19 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Full festival line up & details here!

Iam Tongi – October 22 (Ticketed Show)
2025-10-22 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
You can hear it in the gentle rasp of his wave-washed vocal soul. You can see it in his smile. For Iam Tongi, music is not just about fun – although it definitely is that. It’s about transformation.A Hawaiian-born singer-songwriter and the Season 21 champion of American Idol, the 20-year-old Tongi first saw music transform his family, then his sense of purpose … and then every aspect of his life. And now, as he steps forward with the wind firmly at his back, another transformation begins. Marked by growth, gratitude, and feel-good island wisdom, the rising star looks to the horizon. “I know I’m supposed to be doing this, and sometimes that’s all I know,” the inspiring young talent says. “This is what I was meant for.” That clarity came early for the emerging star. First picking up a ukulele in the fifth grade, Tongi grew up in a deeply musical world filled with community gatherings, each one marked by the traditional singing and dance of Pacific Island cultures. Living in the small town of Kahuku on the northern tip of Oahu – far removed from the tourists on the opposite side of the island – he still has vivid memories of his father and grandfather, singing together in quiet harmony as they sat on the family’s front porch. Both hard-working, blue-collar stoics, they rarely even spoke – letting music do the talking instead. “Everyone knew music and music was life – it’s about just having fun,” Tongi explains. “Everyone knew how, except for me. And I remember I always felt kind of left out.” That changed when Tongi began singing, too, looking for a way to get closer to his dad. Although his father’s regular workday was 16 hours long, he’d still rush home to sing with Tongi, teaching his son what he knew and hammering home the idea that music was Tongi’s path to a better life. Clearly blessed with an expressive, charismatic voice, Tongi was pushed hard and immersed in the multi-faceted skills of island reggae – plus a family record collection that featured country (Kenny Rogers), classic rock (Dr. Hook), and R&B (Luther Vandross). By 13 Tongi had played his first show, singing Tongan classics and his dad’s favorite Dr. Hook song (“Sylvia’s Mother”) at a North Shore fair. With his fluid style, warm vocal rasp and beaming optimism, Tongi easily cut through the din of the inattentive crowd, earning his first taste of the rush live performance offered. But when the family moved to Seattle, music truly became a lifeline. Dropped into a culture he’d only seen on TV, the tender-hearted Tongi was slow to make friends, and found solace in music instead. Writing songs as an outlet and comfort, he also began singing even more – partly because his dad had suffered two strokes and a heart attack, meaning he could no longer work. The pair practiced twice as hard as before, and often livestreamed their duets on Facebook for hundreds of viewers. It was a reminder of home for them both. “I really missed home. And what made me feel like I was home again, was Hawaiian music,” Tongi says. “I never really fit in at school, so I leaned on my music even more. I wrote all the time.” In a devastating blow, Tongi’s father passed away from kidney failure in December 2021 – but not before encouraging his son to keep singing, one last time. Even so, Tongi couldn’t bring himself to do it. Music brought back painful memories, and without his dad, Tongi began to wonder if he had ever loved music at all. The crestfallen teen put his guitar away, and tried to forget. It was his mother who knew better. Secretly signing her son up for American Idol – a dream her late husband had long pushed for – she surprised Tongi with the news just two days before his audition. In one of Idol’s all-time emotional highlights, that moving performance of James Blunt’s “Monsters” immediately went viral, and by the end of Season 21, Tongi had made history as the first Pacific Islander to ever win the show. As he told the world, he did it to honor his father. … But ultimately, the win helped Tongi learn to believe in himself – inspiring millions in the process. The following year presented more challenge. Despite a thriving fanbase that supports millions of global on-demand streams and social media followers, the constant travel of nationwide concert tours and long separation from family led Tongi to wrestle with his new reality, and struggle to speak his creative truth. But a new day dawns. Finding a trusted collaborator and mentor in acclaimed songwriter/producer Johnny Reid, the pair’s instant connection has rekindled Tongi’s creative drive. And after rebuilding the gifted talent’s confidence, dozens of songs have been written for Tongi’s next chapter, each one combining his skill and background in way that is true to himself. “Now, I’m doing what I love,” the rising star says. “I want it to be a fun.”That quest began with “Road to Hana,” a bouncing, windows-down mix of upbeat island reggae and country heart, with a colorful vocal to match. A tribute to Hawaii with a clever romantic twist, Tongi co-wrote the track with Reid and Roy Morgan, and it marks the first taste of a trove of new material. Leaning into Tongi’s cultural heritage and musical roots – but also the man he’s become – breezy beach balladry and sunshine country stand alongside laid-back soul, gospel, and more, as the young artist celebrates the ever-changing magic of music, and life itself. He’s seen the transformation happen (more than once), and through it all, one lesson remains constant: To live each moment for all it’s worth.“I want people to not take things for granted,” Tongi explains. “Don’t wait until you lose someone to look at it like that. Don’t wait until it’s too late, and always stay positive.“It’s actually a really hard thing to do, and this world is already messed up,” he goes on. “What I want people to take from my music is just positivity.”

Country Night w/ Josh Tennessee Worthy Ensemble- October 23
2025-10-23 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

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!

Muhly – October 24
2025-10-24 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Muhly!

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!

Closed for Private Event – October 25
2025-10-25 08:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Closed for Private Event.
More information on how you can book the Oak for your upcoming special event!

No Music – October 26
2025-10-26 08:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Wheeland Brothers w/ Seranation (Ticketed Show) – October 29
2025-10-29 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Wheeland Brothers are two Southern California surfers who grew up where the concrete meets the sand. Their playful pursuit of life invites listeners to join in on the stoke, all the while blending infectious good-time-energy with peaceful introspection. The band has performed with peers ranging from 311 and Slightly Stoopid to Donavon Frankenreiter and Michael Franti. They’ve also performed at Meeting Of The Minds, Tortuga Music Festival, Kaaboo Del Mar, and were personally picked by Kenny Chesney to play the Nashville kick off to his 2022 summer tour. As a headliner, they pack out venues from Coach House in SoCal to Guanabanas in Florida and Big Chill Beach Club in Delaware.

Get Full details and tickets here!

Country Night w/ Cumberland Band – October 30
2025-10-30 19:00 - 22:00
Thursday means one thing at the Oak — Country Night with Pendleton Whisky! Stop by and enjoy live music with us and Cumberland 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!

Closed for Private Event – October 31
2025-10-31 08:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
