Colonial Quarter

Country Night w/ Cumberland Band – October 30
2025-10-30 19:00 - 22:00 UTC
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
Closed for Private Event.
More information on how you can book the Oak for your upcoming special event!

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!

Badfish Tribute to Sublime – November 19
2025-11-19 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Badfish a Tribute to Sublime “Orange you Glad to See Us Tour” w/ Joe Samba!
Full event details here!

Country Night w/ Cliff Dorsey – November 20
2025-11-20 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 Cliff Dorsey!

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 – November 21
2025-11-21 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!

Dyer Davis Band – November 22
2025-11-22 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with The Dyer Davis Band!

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!

Creed Fisher (Ticketed Show) – November 23
2025-11-23 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
CREED FISHER “BETWEEN HEAVEN & HELL TOUR” live in ST AUGUSTINE

Josh Tennessee Worthy Ensemble – November 26
2025-11-26 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!

Closed for Thanksgiving
2025-11-27 08:00 - 17:00

Shay Lynn Band – November 28
2025-11-28 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with the Shay Lynn Band!

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!

Cumberland Band – November 29
2025-11-29 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with Cumberland! Stick around and enjoy this night brought to you by Cazadores Tequila

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 – November 30
2025-11-30 08:00 - 17:00

Toubab Krewe (Ticketed) – December 3
2025-12-03 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Some music cannot be found on a map or within iTunes categories. Some music is so original it seems snatched from the great, invisible substrata that runs below all human activity, a sound aching to be born without a flag or fixed allegiance – free, questing, overflowing with immediate, tangible life. This is the music of Toubab Krewe, the vibrant Asheville, NC-based instrumental powerhouse that creates a sonic Pangaea that lustily swirls together rock, African traditions, jam sensibilities, international folk strains and more. While nearly impossible to put into any box, it takes only a few moments to realize in a very palpable way that one is face-to-face with a true original who recognizes no borders in a march towards a muscular, original, globally switched-on sound. Formed in 2005, Toubab Krewe has tenaciously honed their craft through relentless touring and a fierce dedication to carving out something they can truly call their own. The fruits of this hard work can be heard on their latest release, STYLO, (March 2nd, 2018). What Justin Perkins (kora, kamelngoni, guitar, percussion), Terrence Houston (drumset), Drew Heller (guitar, organ), Justin Kimmel (bass, keys), and Luke Quaranta (djembe, dunun, sangban, kenkeni, kryn, karenye) have wrought on STYLO reflects the many miles and musical journeys that have transpired since their last studio album, TK2. This is a band that actively draws inspiration from whatever source floats into their purview, something they’ve exhibited in their decade and a half of heavy gigging, including regular appearances at major U.S. festivals like Bonnaroo, High Sierra, Electric Forest, Wakarusa, Hulaween, and abroad at such legendary gatherings as the Festival In The Desert in Essakane, Mali, Shanghai World Music Festival, and Jam Cruise. Whether on their own or collaborating with luminaries like the Last Poets’ Umar Bin Hassan, Uncle Earl’s Rayna Gellert, or Weedie Braimah, Toubab Krewe has already earned the attention and respect of a broad musical community. Toubab carries echoes of African greats like Ali Farka Toure, Orchestra Baobab and Salif Keita, no doubt picked up during the group’s travels to study and live in Guinea, Ivory Coast and Mali. But what truly differentiates Toubab Krewe from other Statesiders inspired by African music is how they innovate on what they’ve learned instead of simply recreating tradition. Toubab Krewe carves out a new trail honoring the African originators they admire by making something alive and contemporary.

Cam Wheaton Band – December 4
2025-12-04 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 and the Cam Wheaton 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!

One Good Ring – December 5
2025-12-05 19:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Carry on the music, vibe, & spirit of The Grateful Dead with us and One Good Ring!

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 – December 6
2025-12-06 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 band, Baba Caiman!

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!

Andy Frasco – December 7
2025-12-07 18:00 - 22:00 | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
ANDY FRASCO & THE U.N. have long been the high-flying DIY renegades of the touring scene known and loved for their kaleidoscopic musical fusion and one-of-a-kind onstage audacity. Now celebrating their longevity, the band is shaking things up with L’Optimist (Fun Machine Records/Soundly), as its title suggests, Frasco’s most hopeful and enthusiastic collection thus far. A testament to Frasco’s wide-ranging influences and boundless energy, his band’s sixth released studio album sees the magnetic frontman continuing to chart his path of self-exploration and personal discovery through increasingly introspective lyricism and musical adventure. Songs like “Everything Bagel (Feat. Artikal Sound System)” and the deeply moving “Iowa Moon” touch on matters of the heart and mental health, emotional struggle and the sheer vulnerability of the human experience, all relayed through a wildly eclectic approach navigating funk, jazz, surf rock, blues, swing, gospel, reggae, exotica, and more with horn-blasted positivity and soulful power.“I fight depression every single day,” Frasco says, “and the only way to fight depression is through optimism. I try to write optimistic songs because optimism keeps me going. As humans, I don’t think we’re all that much different. Everyone needs a little optimism to keep going.” Having spent the first part of his career making his bones as a fun-loving frontman with a self-proclaimed “gift of gab,” Frasco pushed his songwriting in more personal directions with 2020’s Keep On Keepin’ On and 2022’s Wash, Rinse, Repeat.
