Colonial Quarter

Country Night w/ Cade and the Palmetto Kickers – October 9
2025-10-09 19:00 - 22:00 UTC | 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
No music today!

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

Josh Tennessee Worthy Ensemble – November 1
2025-11-01 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with The Josh Tennessee Worthy Ensemble!

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!

KISS Alive The Tribute (Ticketed) – November 2
2025-11-02 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Almost 16 years ago, what began as 4 fans wanting to cover KIϟϟ tunes for Florida fans has evolved into one of the country’s premier KIϟϟ tribute acts. Comprised of 4 seasoned musicians, KIϟϟ ALIVE the tribute, has had the honor of being a top finalist for a worldwide KIϟϟ tribute contest, being invited to audition for NBC’s America’s Got Talent, gracing several pages of the July 2014 GOLF DIGEST magazine, and entertaining thousands upon thousands of KIϟϟ fans throughout the United States. We were the winner of the 2020 South Florida Fair Tribute band contest and even more recently, the band was chosen as contestants for the 2021 TV show, CLASH of The TRIBUTES. Slated for at least 3 seasons (we are in season 1), it’s a national “American Idol” type show. Alex Lords as The Demon, Erik Winger as The Catman, James Cullen as The SpaceAce and John Carlazzo as The Starchild all have decades of stage experience to deliver the absolute best show possible sure to please any level of KIϟϟ fan. From the music to the costumes to the fire-breathing and blood-spitting and complete over-the-topness of the show, including newly added production, KIϟϟ ALIVE the Tribute brings excitement, passion and commitment to each and every performance.

TICKETS & MORE INFO HERE

Shwayze (Ticketed Show)- November 5
2025-11-05 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Raised on the beaches of Southern California, Aaron Smith is a rapper, actor, musician, and father who became known to the world simply as Shwayze following a massive music breakout in 2008.‍The Malibu native released his debut album Buzzin’ that summer with singer-producer Cisco Adler. The duo hit the road immediately on the Vans Warped Tour wearing skinny jeans, and singing about lost weekends in Hollywood, all while bringing the most legendary parties with them wherever they went.Shwayze has since gone on to work with an array of producers and release several independent albums such as Shwayze Summer on his self-funded Feel Good Entertainment Music label. He continues reinventing his sound while staying true to the influences that brought him where he is today.

Tickets and more info here!

Country Night w/ Whalin – November 6
2025-11-06 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 Whalin!

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!

New Master Sounds (Ticketed Show) – November 7
2025-11-07 18:00 - 22:00
The New Mastersounds have been delighting audiences with their infectious brand of funky soul-jazz since they formed in Leeds, England in 1999. For the first five years of the band’s career they were regulars at the Jazz Café in London, before they began to turn heads on the funk scene in the US, where guitarist/producer/bandleader Eddie Roberts now lives. For over a decade they have been a staple act of the late-night scene during New Orleans’ annual Jazz Fest. Always happy to hit the studio between tours, this veteran band now boasts a rich recorded catalogue that includes fifteen original studio albums, four live albums, several compilations, and a remix album. Though they have collaborated over the years with such musical luminaries as Maceo Parker, Fred Wesley, Corinne Bailey Rae, Art Neville, Bernard Purdie and Lou Donaldson, they are at their best on stage as a tightly-packed quartet – bass, drums, guitar and keyboards – firing off scorching grooves and feeding on the energy of the dancers in the front row.​​​​

LINK TO TICKETS & MORE INFO

Closed for Private Event – November 8
2025-11-08 08:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Closed for Private Event

Celebrate your special occasion at the Oak! Click here to learn more!
Follow us on Instagram to see our latest weddings & special events! @thecolonialoakevents
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No Music – November 9
2025-11-09 08:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
No music today

Satsang (Ticketed Show) – November 12
2025-11-12 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Satsang is a dynamic musical ensemble that weaves together elements of folk, soul, and conscious lyrics to create a captivating sonic experience. Comprised of talented musicians and led by frontman Drew McManus, Satsang embodies the spirit of connectivity, spirituality, and social awareness through their music.
Drawing inspiration from a diverse array of musical traditions, Satsang’s sound is characterized by rich harmonies, infectious rhythms, and thought-provoking lyrics that resonate with audiences across the globe. With roots in the mountains of Montana, the band’s music reflects the natural beauty and spiritual depth of their surroundings, while also addressing contemporary issues and themes.
At the heart of Satsang’s music is a message of unity, compassion, and mindfulness. Through their uplifting melodies and introspective lyrics, the band encourages listeners to reflect on their own experiences, cultivate empathy for others, and embrace the interconnectedness of all beings.
With a reputation for captivating live performances and a dedicated fan base, Satsang continues to inspire audiences with their soul-stirring music and heartfelt lyrics. Whether performing at intimate venues or large festivals, the band’s infectious energy and profound message leave a lasting impression on all who hear them.
In a world that often feels divided, Satsang offers a beacon of hope and positivity through their music, reminding us all of the transformative power of community, love, and consciousness.
Use the share tools on this event page to let your friends know where you will be. Please Print a PDF ticket for entry into the event, or your phone or email can also work. No Refund Event. Rain or Shine Event.
6-10 PM

Tickets and more info here!

Country Night w/ Muhly – November 13
2025-11-13 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 Muhly!

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!

Josh Tennessee Worthy Ensemble – November 14
2025-11-14 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Closed for Private Event – November 15
2025-11-15 08:00 - 17:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Closed for Private Event
Celebrate your special occasion at the Oak! Click here to learn more!
Follow us on Instagram to see our latest weddings & special events! @thecolonialoakevents

Surfer Girl (SOLD OUT) – November 16
2025-11-16 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Surfer Girl returns to the Oak on Sunday, November 16th!
SURFER GIRL
Surfer Girl – led by the dynamic Carter Reeves, former frontman of the acclaimed hip-hop/pop group Aer – continues to evolve and captivate audiences with their distinct blend of indie-pop, reggae, surf-rock, and hip-hop. Hailing from Wayland, MA, Carter’s laid-back coastal vibes are ever-present in the band’s sound, which effortlessly blends sun-soaked melodies with infectious rhythms that evoke the feeling of a carefree summer afternoon. With the release of their highly anticipated new album Sunset in April 2025, Surfer Girl takes their sound to new heights. The album features collaborations with an exciting lineup of artists, including Bryce Vine, Collie Buddz, Jah Lil, Emily Brimlow, and more. From breezy anthems to introspective tracks, Sunset captures the essence of summer, love, and living in the moment. Surfer Girl’s magnetic live performances continue to make waves on major festival stages. In 2025, they’re bringing their high-energy, feel-good vibes to Vans Warped Tour in Orlando, following their memorable appearances at Sea.Hear.Now, SunFest, Cali Vibes, and Reggae Rise Up. Known for his powerful stage presence, Carter Reeves and the band create a live show that’s both nostalgic and refreshing, sweeping audiences away with every note. As a seasoned performer, Carter Reeves and Surfer Girl bring a perfect blend of musical mastery and laid-back beach culture to every stage they grace – making each performance an unforgettable experience.
TESSELLATED
With Jamaican influence on international music inescapable in the current era, a new wave of exciting artists is emerging from the Caribbean island. One artist leading the charge for this global assault on the music industry is Tessellated, a multi-talented 24 year old Grammy & Emmy artiste/producer from Kingston who burst onto the scene in 2017 with his bona fide Caribbean hit collaboration – Pine & Ginger. Citing influences from many genres, a unique blend of styles and sounds shapes the backdrop for Tessellated’s musical endeavour. Through this, he aims to push forward a fusion of Jamaica’s roots presented alongside other world genres. With this original style, Tessellated has now carved out a lane of his own already garnering support from music industry heavyweights such as Camila Cabello, Lily Allen, Shaggy, Diplo, Major Lazer, Jorja Smith, Dua Lipa and more.
Tickets & more info HERE!

Surfer Girl (NIGHT 2) – November 17
2025-11-17 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Night 2 of Surfer Girl at the Oak!!!
SURFER GIRL
Surfer Girl – led by the dynamic Carter Reeves, former frontman of the acclaimed hip-hop/pop group Aer – continues to evolve and captivate audiences with their distinct blend of indie-pop, reggae, surf-rock, and hip-hop. Hailing from Wayland, MA, Carter’s laid-back coastal vibes are ever-present in the band’s sound, which effortlessly blends sun-soaked melodies with infectious rhythms that evoke the feeling of a carefree summer afternoon. With the release of their highly anticipated new album Sunset in April 2025, Surfer Girl takes their sound to new heights. The album features collaborations with an exciting lineup of artists, including Bryce Vine, Collie Buddz, Jah Lil, Emily Brimlow, and more. From breezy anthems to introspective tracks, Sunset captures the essence of summer, love, and living in the moment. Surfer Girl’s magnetic live performances continue to make waves on major festival stages. In 2025, they’re bringing their high-energy, feel-good vibes to Vans Warped Tour in Orlando, following their memorable appearances at Sea.Hear.Now, SunFest, Cali Vibes, and Reggae Rise Up. Known for his powerful stage presence, Carter Reeves and the band create a live show that’s both nostalgic and refreshing, sweeping audiences away with every note. As a seasoned performer, Carter Reeves and Surfer Girl bring a perfect blend of musical mastery and laid-back beach culture to every stage they grace – making each performance an unforgettable experience.
TESSELLATED
With Jamaican influence on international music inescapable in the current era, a new wave of exciting artists is emerging from the Caribbean island. One artist leading the charge for this global assault on the music industry is Tessellated, a multi-talented 24 year old Grammy & Emmy artiste/producer from Kingston who burst onto the scene in 2017 with his bona fide Caribbean hit collaboration – Pine & Ginger. Citing influences from many genres, a unique blend of styles and sounds shapes the backdrop for Tessellated’s musical endeavour. Through this, he aims to push forward a fusion of Jamaica’s roots presented alongside other world genres. With this original style, Tessellated has now carved out a lane of his own already garnering support from music industry heavyweights such as Camila Cabello, Lily Allen, Shaggy, Diplo, Major Lazer, Jorja Smith, Dua Lipa and more.
Tickets & more info HERE!
