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!

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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!

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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!

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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,
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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.

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Whalin (Country Night) – May 21st
2026-05-21 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 Whalin and us!
Whalin is a high-energy country band bringing classic honky-tonk spirit and rock-and-roll edge to the stage. Formed by Lane Whalin after returning from a six-month tour with Ashley Wineland, the group features a lineup of talented musicians from across North Florida. Their setlist blends fan-favorite country songs with a few rock-inspired moments that keep the crowd moving. Catch Whalin performing on stages throughout Florida and Georgia as they deliver a lively mix of modern and classic country sounds.

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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Cliff Dorsey (Country Night) – May 28
2026-05-28 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 Cliff Dorsey and us!
Cliff Dorsey, a country artist from High Springs, Florida, now based in Nashville, brings a deep baritone and heartfelt storytelling that echoes the legends of classic country. His songs capture the spirit of traditional country while sharing his own modern twist.

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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Tell Me Lies (Ticketed) – May 31
2026-05-31 18:00 - 22:00 (America/New_York) | Colonial Oak Music Park, 21 St George Street, St Augustine, FL, 32084, United States
TELL ME LIES TRIBUTE
Tell Me Lies showcases the timeless hits of Fleetwood Mac, a band renowned for their exceptional song writing and energetic live performances. The accomplished members of Tell Me Lies have been creating music together in various styles and combinations for many years. It was only natural for them to unite and honor the unmatched legacy of Fleetwood Mac. With an unwavering commitment to authenticity and a deep respect for their craft, Tell Me Lies meticulously recreates the beloved sounds and visuals of one of the world’s most adored best-selling bands.
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