Colonial Quarter

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 | 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 | 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 | 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!

Click here for Instagram!
Click here for Facebook!

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

Click here for Instagram!
Click here for Facebook!

The Casualties – December 14
2025-12-14 18:00 - 22:00 | 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 | 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!
Click here for Facebook!

Dyer Davis Band – December 19
2025-12-19 19:00 - 22:00
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!

Click here for Instagram!
Click here for Facebook!

Brett Blackshear & Dewey Via Band – December 20
2025-12-20 14:00 - 22:00 | 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!
Click here for Facebook!

Winter Wonder Jams – December 21
2025-12-21 15:00 - 22:00 | 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!
Click here for Facebook!

Winter Wonder Jams – December 22
2025-12-22 15:00 - 22:00 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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!
