St. Augustine, FL | Oldcity.com

Romanza Festivale 2026
2026-05-03 18:00, 2026-05-04 18:00, 2026-05-05 18:00, 2026-05-06 18:00, 2026-05-07 18:00, 2026-05-08 18:00, 2026-05-09 18:00, 2026-05-10 18:00 (America/New_York) and 7 more dates | Downtown St. Augustine, St. Augustine, FL, 32084, United States
Romanza Festivale of Music and The Arts 2026
It’s time for the annual Romanza Festivale of Music and The Arts! Comprised of over 40 headline and partner events featuring music, dance, visual arts, theatre, spoken word, and more at several locations throughout St. Augustine. And … best of all … most events are Free!
When: May 1-17, 2026 — times vary by day/event
The Festivale showcases productions by dozens of talented Arts and Cultural non-profit organizations.
Headliners (to be announced)
You can find all sorts of details … including a full list of events and venues … by clicking the event website link. Information will be updated as it becomes available.

Ethel Cain at The Amp
2026-05-08 19:00 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
Ethel Cain and The Willoughby Tucker Forever Tour is at the St. Augustine Amphitheatre with special guest 9million — Friday, May 8, 2026.
Cain is the creation of Florida-born, multidisciplinary artist Hayden Anhedönia. After spending years teaching herself to produce at home and releasing various projects, Cain moved to Indiana. There she single-handedly wrote, produced, recorded and mixed her acclaimed 2021 EP ‘Inbred’ from the basement of the old church where she lived.
Since then, Cain has released three bodies of work. Her 2022 debut album ‘Preacher’s Daughter’ was released in May 2022 to widespread praise with many critics naming the album one of the best of the year. In 2025, she unveiled ‘Perverts’ and her sophomore LP ‘Willoughby Tucker, I’ll Always Love You’ – both to near-universal acclaim.
Gates Open 5:30pm | Show 7:00pm
Click event website link for all the details including ticket prices. Tickets can also be purchased at the newly renovated Box Office … open seven days a week from 7:00am to 5:00pm – only accepting credit / debit cards for payment.

Gamble Rogers Concert Series
2026-05-16 19:00, 2026-06-20 19:00 | The Waterworks, 184 San Marco Avenue, St.Augustine, 32084
Live from The Waterworks – Gamble Rogers Concert Series 2025-2026
These monthly concerts at The Waterworks celebrate the legendary recording artist Gamble Rogers, whose balladry and storytelling shaped American folk music. They feature a variety of talented musicians from across the country (regional or national headliners) as well as a rising YoungFolk opener.
Performance Schedule
October 18, 2025 — The New 76ers
November 22, 2025 — Jordan Tice
December 20, 2025 — A Guitar Outlaw Christmas
January 17, 2026 — Robert Bowlin & Wil Maring
February 21, 2026 — Sunny War
March 21, 2026 — Pat Bergeson & Bruce Forman
April is the Gamble Rogers Folk Festival at the SJC Fairgrounds
May 16, 2026 — Walter Parks
June 20, 2026 — Guy Davis
Doors Open at 6:30 | Show at 7:00pm
Libations available for purchase.
Ticket Information
Tickets go on sale Tuesday, August 26, at 10:00am. There are only 120 seats per show … so, tickets will go fast!
General Admission: $30.00 | VIP (front of house seating): $40.00
Click the event website link to purchase your tickets and for all additional information.
Presented in partnership with The St. Johns Cultural Council.

Sam Barber at The Amp
2026-05-23 19:00 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
Sam Barber is at the St. Augustine Amphitheatre for The American Route Tour … with special guests Michael Marcagi and Bebe Stockwell – Saturday, May 23, 2026.
Barber claimed his space in the country spotlight with the breakout success of his RIAA Gold-certified 2024 debut album, ‘Restless Mind’. The 28-song, tour-de-force is highlighted by such smash singles as the 2x RIAA Platinum certified “Straight and Narrow”, “Better Year”, and the RIAA Platinum-certified “Indigo (Feat. Avery Anna)”. The latter has proven a worldwide sensation with over 500M global streams, also earning Platinum certification in Australia and 2x Platinum certification in Canada. That’s while spending 14 weeks and counting among the upper reaches of country radio airplay charts nationwide and reaching the top 40 on Billboard’s overall Hot 100.
As if all that weren’t enough, last year saw Barber’s “Tear Us Apart” among the standout tracks featured on Lockeland Springs/Atlantic Records’ RIAA Gold-certified, GRAMMY® Award-nominated blockbuster soundtrack, Twisters: The Album. He’s kept his unstoppable momentum going this year with his acclaimed new EP, ‘Music for the Soul’. The EP sees Barber chronicling how he got here and where he’s headed next on such eloquent, empathetic new songs as “Same Sad Shit”, the fame-wrestling title track, “Music for the Soul”, and the deeply moving “Home Tonight”.
Gates Open 5:30pm | Show 7:00pm
Click event website link for all the details including ticket prices. Tickets can also be purchased at the newly renovated Box Office … open seven days a week from 7:00am to 5:00pm – only accepting credit / debit cards for payment.

Kaleidoscope - Open Mic + Art Showcase
2026-05-24 19:00, 2026-06-14 19:00 | Limelight Theatre, 11 Old Mission Avenue, St. Augustine, FL, 32084, United States
Kaleidoscope – Open Mic + Art Showcase
Calling all creative people to the Limelight Theatre for Kaleidoscope. This FREE event gives artists and extraordinary people a platform to share their talent and creations in a safe space.
People can perform spoken word poetry, original music, standup comedy, and even karaoke. Visual artists display their canvases, prints, jewelry, and crafts. Writers display their books.
These Sunday evenings are ones to remember in a cabaret setting.
Schedule – 7:00pm on:
August 24, 2025
September 28, 2025
October 26, 2025
November 30, 2025
December 28, 2025
January 25, 2026
February 22, 2026
March 29, 2026
April 19, 2026
May 24, 2026
June 14, 2026
So … come sing, spit poetry, tell jokes and/or stories, vibe out with your instrument, bring your artist endevouer — prints, books, handmade goods, jewelry, etc…
Click the event website link for all additional information.

Sundays With SAMF
2026-05-31 15:00 - 17:00 | The Waterworks, 184 San Marco Avenue, St.Augustine, 32084
Sundays With SAMF
Save the dates for the Sundays With SAMF concerts … celebrating St. Augustine Music Festival’s 20th Anniversary in 2026! The concerts will be held at The Waterworks. And, the musicians/programs are in the works.
Performance Dates for 2026
Sunday, January 18
Sunday, February 8
Sunday, March 22
Sunday, April 19
Sunday, May 31
Time: 3:00pm-5:00pm
Cost: to be announced.
Keep checking back for updated information.

St. Augustine Music Festival 2026
2026-06-19 19:00, 2026-06-20 19:00, 2026-06-21 19:00, 2026-06-26 19:00, 2026-06-27 19:00, 2026-06-28 19:00 | Cathedral Basilica of St. Augustine, 38 Cathedral Place, St. Augustine, FL, 32084, United States
St. Augustine Music Festival 2026
Be sure to save the dates for one of the nation’s largest, free classical music festivals … the St. Augustine Music Festival 2026. Celebrating two decades of world-class music in a beautiful setting!
When: Friday, Saturday & Sunday | June 19-21 and June 26-28, 2026 at 7:30pm (doors open at 7:00pm).
Where: The Cathedral Basilica of St. Augustine … providing a beautiful backdrop as well as excellent acoustics!
Performance Schedule (to be announced — keep checking back)
The mission of the St. Augustine Music Festival is to produce, perform, and promote a world-class traditional and contemporary classical/chamber music experience to a diverse audience in an accessible, welcoming, and uplifting environment to enhance the quality of life within the community through the inspiring power of music.

O.A.R. Three Decades Tour at The Amp
2026-11-14 18:30 | St. Augustine Amphitheatre, 1340C A1A South, St. Augustine, FL, 32080, United States
O.A.R. is at the St. Augustine Amphitheatre with their Three Decades Tour on Saturday, November 14, 2026 … with special guests Gavin Degraw and KT Tunstall.
Unbelievably, O.A.R. is still together thirty years since their first gig at an eighth grade talent show. But, these musicians are no strangers to “unbelievable”. In fact, they’ve quietly shattered expectations at every turn over the last thirty years. Their journey may have started in Maryland, but it’s taken them around the world with multiple sold-out shows at Madison Square Garden and Red Rocks Amphitheatre, north of 1 billion streams, and multiplatinum success.
Creating an expansive catalog beginning with 1997’s ‘The Wanderer’, they earned RIAA Gold certifications as well as three Top 15 Billboard 200 debuts. And, they have collaborated with everyone from Robert Redford and Goo Goo Dolls to Wiz Khalifa and DJ Premier. Their latest album, ‘The Arcade’, features the fan favorite “In the Clouds”.
O.A.R. members, Marc Roberge and Jerry DePizzo, are also founding partners of the Oceans Calling Festival in Ocean City, Maryland. The festival is a world-class, multi-day celebration of music and community. And, through their charity, Heard The World Fund, O.A.R. has raised millions for education, sustainability, and pediatric cancer causes.
Heading into their 30th year in 2026, Marc Roberge, Richard On, Chris Culos, and Jerry DePizzo are still having a blast as brothers. And, it shows every time they take the stage.
Gates Open 5:30pm | Show 6:30pm
Click event website link for all the details including ticket prices. Tickets can also be purchased at the newly renovated Box Office … open seven days a week from 7:00am to 5:00pm – only accepting credit / debit cards for payment.
