Shay Lynn Band – November 28
2025-11-28 19:00 - 22:00 UTC | 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!

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Cumberland Band – November 29
2025-11-29 19:00 - 22:00 UTC | 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!

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No Music – November 30
2025-11-30 08:00 - 17:00 UTC
No Music Today

Toubab Krewe (Ticketed) – December 3
2025-12-03 18:00 - 22:00 UTC | 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 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 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!

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One Good Ring – December 5
2025-12-05 19:00 - 22:00 UTC | 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!

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Baba Caiman – December 6
2025-12-06 19:00 - 22:00 UTC | 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!

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Andy Frasco – December 7
2025-12-07 18:00 - 22:00 UTC | 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.

Coyote Island (Ticketed) – December 10
2025-12-10 18:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Equilibrium depends on music. Body, mind, and soul move in a perfect harmony together. Synapses fire and hearts thump in time like a drumbeat. In this respect, the right tune sung at the right moment works like the best kind of natural medicine. Maine-based singer, songwriter, producer, and multi-instrumentalist Coyote Island—a.k.a. Mike O’Hehir—recognizes and reveres the restorative potential of songcraft. Mixing folk, reggae, pop, world, cumbia, and psychedelia, he stirs up a sonic elixir meant to invigorate and inspire.

Ticket and more information here!

Ax & the Hatchetmen (Ticketed Show) – December 11
2025-12-11 18:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
AX AND THE HATCHETMEN are a 6 piece indie rock band led by Axel Ellis. The Chicago based band’s shimmering two guitar attack, earthy rhythms and blistering horns have gained them a loyal following nationwide. Formed in 2018, the camaraderie and musicality between the long-time group of friends is apparent the moment they take the stage. They plan on touring and releasing music for the foreseeable future. They also will party.

JOHN-ROBERT
John-Robert has been a notable performer since he was a child, it is simply what he was born to do. At only 13 years old, John-Robert was handpicked to perform on the Ellen show as a musical child prodigy. At 19, he left his hometown Edinburg, VA (pop. 1,070) in 2019 to move to LA and start his music career, bypassing a scholarship to Berklee. He was signed to Nice Life/ Warner by Grammy-nominated producer Ricky Reed (Leon Bridges, Lizzo) and released a handful of singles and EPs over a few years, earning him co-signs from artists Alessia Cara and Camilla Cabello. But it was a live fireside performance of his 2023 song “Come Pick Me Up” that catapulted John-Robert’s lilting blend of traditional folk and Appalachian country into the modern pop landscape. He toured extensively in 2023 and 2024 in the US and abroad supporting artists like Madi Diaz, Rayland Baxter, Leon Bridges and even Liam Gallagher. Virginia, and his family there, has always been a source of inspiration for the singer-songwriter. On making his 2023 EP Garden Snake he says, “It was like trying to make a Virginia record in LA.” A move back home to Virginia in early 2025 made perfect sense as he embarked on creating a new body of work. The move was a way to pull himself out of the professional and personal turmoil of LA, and reconnect with the people and places that made him who he is today – the banks of the North Fork Shenandoah River and rolling hillsides, the home-cooked meals and close-knit community. Expect more music and live shows from John-Robert throughout 2025 and beyond.

Circus – December 12
2025-12-12 19:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak with classic rock band, Circus!

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!

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Versvtile – December 13
2025-12-13 19:00 - 22:00 UTC
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!

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The Casualties – December 14
2025-12-14 18:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Formed in New York City in 1990, The Casualties are a cornerstone of the modern street punk movement. Known for their explosive live shows, high-energy sound, and fierce dedication to punk’s raw roots, the band has spent over three decades carrying the torch of anti-establishment rebellion and working-class unity. Drawing inspiration from classic UK punk like The Exploited and Discharge, The Casualties blend aggressive riffs, shouted choruses, and politically charged lyrics into a relentless sonic assault. Their discography includes landmark releases such as For the Punx, Die Hards, On the Front Line, and Chaos Sound, each solidifying their status as global ambassadors of hardcore street punk. Following the retirement of founding frontman Jorge Herrera in 2017, David Rodriguez (Krum Bums, Starving Wolves) stepped in as lead vocalist, ushering in a new era without compromising the band’s fierce identity. With over 30 years of relentless touring, international acclaim, and uncompromising music, The Casualties remain one of punk’s most enduring and vital forces.
Tickets and more info here!

Country Night w/ Cumberland Band – December 18
2025-12-18 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 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!
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Dyer Davis Band – December 19
2025-12-19 19:00 - 22:00 UTC
Join us at the Oak with the Dyer Davis Band on December 19th!

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!

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Brett Blackshear & Dewey Via Band – December 20
2025-12-20 14:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Join us at the Oak for free live music!
Brett Blackshear 2-5 PM
Dewey Via Band 7-10 PM

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!
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Winter Wonder Jams – December 21
2025-12-21 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
This winter we’re bringing a rotating lineup of St. Augustine’s favorite local musicians to the Oak with our FREE seasonal series – Winter Wonder Jams! A mix of familiar faces and fresh talent coming together to keep the music flowing all season long.
Our opening 3–6 PM set will roll right into an evening performance, so whenever you stop by, you can count on live music under the Oak.
Come grab a drink, enjoy the lights, and celebrate the season with us!

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!
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Winter Wonder Jams – December 22
2025-12-22 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Winter Wonder Jams – December 23
2025-12-23 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
This winter we’re bringing a rotating lineup of St. Augustine’s favorite local musicians to the Oak with our FREE seasonal series – Winter Wonder Jams! A mix of familiar faces and fresh talent coming together to keep the music flowing all season long.
Our opening 3–6 PM set will roll right into an evening performance, so whenever you stop by, you can count on live music under the Oak.
Come grab a drink, enjoy the lights, and celebrate the season with us!

FREE show
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!

Sam Pacetti – December 24
2025-12-24 17:00 - 20:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Enjoy music by Sam Pacetti on December 24 from 5-8 PM

Winter Wonder Jams – December 26
2025-12-26 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Winter Wonder Jams – December 27
2025-12-27 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Winter Wonder Jams – December 28
2025-12-28 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Winter Wonder Jams – December 29
2025-12-29 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

Winter Wonder Jams – December 30
2025-12-30 15:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States

2026 NYE Countdown with the Dewey Via Band!
2025-12-31 14:00 - 23:30 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
We’re ringing in the New Year with Sam Pacetti 2-5 PM followed by the Dewey Via Band at 7PM!

Supervillains – January 7
2026-01-07 18:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
The Supervillains are a high-energy ska and reggae band hailing from Florida, known for their infectious grooves and lively performances. Formed in the late 1990s, the band blends elements of ska, reggae, rock, and punk, creating a sound that’s both catchy and rebellious. With their upbeat rhythms, humorous lyrics, and a reputation for high-octane live shows, The Supervillains have earned a loyal fanbase and are a standout act in the South Florida music scene.

Get tickets and more info here!

Kelly Daniels Band (Country Night) – May 7
2026-05-07 19:00 - 22:00 (America/New_York) | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Thursday at the Oak means one thing — Country Night with Pendleton Whisky!
Stop by and groove with Kelly Daniels and us!

Come out to Colonial Oak Music Park for a night of great country music under the oaks. If you’re looking for your country fix, we’ve got you covered.
Join us for live music, cold drinks, and a laid-back night in the heart of St. Augustine. Come see Kelly Daniels and enjoy an evening of country sounds you won’t want to miss.

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!

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BADFISH (Ticketed Show) – May 13
2026-05-13 18:00 - 22:00 (America/New_York) | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
BADFISH – a Tribute to Sublime
The phenomenon known as Sublime, arguably the most energetic, original and uniquely eclectic band to emerge from any scene, anywhere, ended with the untimely death
of lead singer, guitarist and songwriter Brad Nowell in May of 1996. But encompassing the sense of place and purpose long associated with Sublime’s music, Badfish, a Tribute to Sublime continues to channel the spirit of Sublime with a fury not felt for some time. What separates Badfish from other tribute bands is that they have replicated Sublime’s essence, developing a scene and dedicated following most commonly reserved for label-
driven, mainstream acts. Badfish make their mark on the audience by playing with the spirit of Sublime. They perform not as Sublime would have, or did, but as Badfish does!
GRATEFUL DUB: a Reggae-infused tribute to the GRATEFUL DEAD – RoC (Roots of Creation) has taken on a unique new project: Grateful Dub: a Reggae-infused tribute to the Jerry Garcia & The Grateful Dead. Combining their longtime love for Reggae-Dub style music and the Grateful Dead, RoC reworked some of the world’s favorite Dead tunes into a new studio album. RoC had the pleasure of working in the studio with the legendary 5-time Grammy winner Errol Brown who was Bob Marley’s sound engineer for this project. Grateful Dub is also being performed live in its entirety at festivals, theatres, and clubs around the country, and features rotating live special guests that has included Melvin Seals (Jerry Garcia Band), Scott Guberman (Phil Lesh), Zach Nugent, RyMo, AG, & Paul W. (Slightly Stoopid), G. Love (G. Love & Special Sauce), Mihali (Twiddle), Dan Kelly (Fortunate Youth) and others. Grateful Dub captures the spirit and magic of the Grateful Dead, while laying it down Reggae-Dub style.
GRIEVES
Born in Chicago, Illinois, Benjamin Laub better know as Grieves was exposed to music at a young age by his father who would take him to Jazz and Blues clubs. After moving to Fort Collins, Colorado, Grieves began to explore the sounds of Punk Rock and Hip Hop. Completely immersed in the art-form, Grieves truly began honing his craft when he moved to seattle at 19. After self-releasing his debut album Irreversible in 2007, Grieves took that momentum out on the road developing an ever growing fan base from the west coast to the east coast.While in Seattle, Grieves would eventually hook up with a talented producer and multi-instrumentalist by the name of Budo. In 2008 the duo would hook up and create 15 tracks of sample-free, melody-driven, analog warmth titled 88 Keys & Counting. A combination of singing and rapping tethered together by guitar, horn, and keyboard driven instrumentals. Although ultimately an intense album, there are a few breaks with sounds like “Identity Cards” (featuring Luckyiam of Living Legends fame) and “Greedy Bitch”, a catchy break up song that will be stuck in your head for days after hearing it. Mainly a digital release, 88 Keys & Counting was welcomed with rave reviews of this new refreshing talent.Now residing in New York City, Grieves and Budo are hard at work finishing his 2010 Rhymesayers debut. So while the world has to wait a little longer for this masterpiece, Rhymesayers is proud to present 88 Keys & Counting,
Click To Get Tickets

Protoje (Ticketed Show) – May 20
2026-05-20 18:00 - 22:00 UTC | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
Protoje is the name that reverberates at the core of Jamaica’s musical renaissance. A visionary and an architect of sound, Protoje has redefined what it means to be a modern artist, blending the rich heritage of reggae with the fresh influence of hip-hop, soul, and jazz. From his roots in Saint Elizabeth, Jamaica, Protoje’s journey is one marked by passion, purpose, and an unwavering commitment to his craft. In 2014, with his iconic track “Who Knows” ft. Chronixx, Protoje became a prominent figure of the “reggae revival” movement. But it didn’t stop there—his journey took him to uncharted territory, collaborating with global superstars like Jorja Smith, Alicia Keys, Pa Salieu, Wiz Khalifa and many more. His track“Switch It Up” ft. Koffee made its way into Barack Obama’s 2021 Summer Playlist, a testament to Protoje’s cross-generational appeal and cultural resonance. But Protoje’s influence extends beyond just his music. He’s the founder of In.Digg.Nation Collective, a platform built to uplift the next wave of Jamaican talent, which nurtured artists like Sevana, Lila Iké, and Jaz Elise. His catalog of albums—each one a reflection of the time—shows his ability to evolve and push the boundaries of what reggae can be. In November 2023, he reimagined his 2020 album In Search of Lost Time with the audacious In Search of Zion, a deep dive into the experimental realms of dub, showcasing his fearless exploration of sound. With two Grammy nominations for Best Reggae Album, for A Matter of Time(2018) and Third Time’s The Charm (2022), Protoje’s name is etched alongside the greats. From Rolling Stone to Vogue, from The Tonight Show Starring Jimmy Fallon to NPR’s Tiny Desk Concert, Protoje’s reach is vast, transcending borders and genres, leaving an indelible mark on the global stage. His performances at Coachella, Glastonbury, andLollapaloozahave solidified him as one of the most dynamic forces in modern music. Protoje is more than an artist; he is a cultural catalyst who’s redefined what it means to be a Jamaican musician in the 21st century. Uncompromising, boundary-pushing, and constantly evolving—Protoje is not just part of the conversation; he is creating it.

Click here for tickets and more information!
