DOWNTOWN HISTORIC PENSACOLA SCHEDULE BY VENUE – Pensacola Beach Songwriters Festival

Shows are Free, unless otherwise indicated. Schedules are subject to change, please check back for updates.

DOWNTOWN PENSACOLA SHOWS – FIRST PBSF WEEK OF SEPT 29-Oct 4, 2026

511 – WINGS & STRINGS

Ticketed Event

Friday, Oct. 2

7:00pm– CJ Solar | Rick Huckaby | Lauren Mascitti

8:00pm– Brian White | Jason Sever | Michael Dulaney

CALVERTS – Songs on the Bay

Friday, Oct. 2

6:00pm– Grace Michelle | Kirstie Kraus | Caitlyn Mae

7:00pm – Teea Goans | Sadie McLayne | Karli Ryan

8:00pm – Will Hutchens | Barry Hutchens | Billy Droze

9:00pm – Kensie Coppin | Gary Nichols | Eli Hannon | Trey Nichols

Saturday, Oct. 3

6:00pm – Thom Shepherd | Coley McCabe Shepherd | Jacob Rice

7:00pm – Dan Alley | Shane Minor | Mitch Oglesby

8:00pm – Brian White | Jason Sever | Michael Delaney

9:00pm – Woody Bradshaw

FROM THE GROUND UP COMMUNITY GARDEN

TUE SEPT 29 – OPEN MIC SHOWCASE – $10 Suggested Love Donation

Hosted by Katie Dineen – Featuring Gulf Coast Area Songwriters

6:30pm – 9pm – Free Admission

HELLCAT HANGAR

FRI OCT 2 * 12:30pm – 3:00pm

LET FREEDOM SING! Free Admission

(Meet and Greet /Food Truck Available)

12:00pm -Doors Open

12:30pm –Presentation of Colors

Blue Anchor Belles

Jason Justice | Kevin Swanson | Shawn Bowling

Matt Williams | Payton Taylor | Brandon Sandefur

Woody Bradshaw

Veteran Writes with Songwriters Performance:

Brian White | Jason Sever | Michael Dulaney

LUCYS IN THE SQUARE

Friday, Oct. 2

4:00pm – 6:00pm – Open Mic

6:00pm – Josh Miller | Sandra Kaye Hinnant

7:00pm – Dustin Dale Gaspard | James Adkins

Saturday, Oct. 3

4:00pm– 6:00pm -Open Mic

6:00pm – Devin Dunlap | Brennan Lowery

7:00pm – Christina Crystal | Kirstie Kraus

OYSTER BAY COURTYARD SERIES – Ticketed Event $35

Saturday, Oct. 3

6:00 pm – Will Hutchens | Barry Hutchens

7:00pm – Anthony Smith | Chuck Cannon | Bob DiPiero

8:00pm – Thompson Square | Jamie Floyd

PICKIN’ ON THE PORCH – TANNER REALTY

421 E Zarragossa St – Pensacola

Friday, Oct. 2

1:00pm – Logan Vath | Tanya Gallagher | Dustin Dale Gaspard

2:00pm – Teea Goans | Lauren Mascitti | Naomie Celestin

Saturday, Oct. 3

1:00pm – Jonathan Puzan | Brandon Sandefur | Tris Weeks

2:00pm – Presley & Taylor

PICKIN’ ON THE PORCH – ALCANIZ PORCH

210 S Alcaniz St – Pensacola

Friday, Oct. 2

2:00pm – Will Hutchens | Barry Hutchens | Troy Castellano

3:00pm – Thom Shepherd | Coley McCabe | Jacob Rice

Saturday, Oct. 3

2:00pm –Kat Deal | Caitlyn Mae | Sadie McLayne

3:00pm – Jeff Silvey | Dana Black | Brian White | Karen Williams

RADIOLIVE – Ticketed Event – tickets

Thursday, Oct 1

David Gautreau |

SEVILLE QUARTER – APPLE ANNIES

Sunday, Oct. 4

DOWNTOWN FINALE – FREE ADMISSION

1:00pm – Sugarcane Jane

2:00pm – Kensie Coppin | Trey Nichols | Eli Hannon | Gary Nichols

3:00pm– Rick Huckaby | Mark Nesler | CJ Solar

4:00pm – Keith Burns | | Anthony Smith | Jamie Floyd

5:00pm – The Family Band

Songs of Worship – VENUE TBA

Sunday, Oct. 4

Hosted by Robert Wayne Walkup

THE DISTRICT – TICKETED EVENTS $30

Thursday, Oct. 1

5:00pm – Dustin Dale Gaspard | Michael Magno | Juliette Stewart

6:00pm– Dana Black | Jeff Silvey | Barry Hutchens

7:00pm – CJ Solar | Rick Huckaby | Payton Taylor

8:00pm – Brian White | Michael Dulaney | Jason Sever

9:00pm– Gary Nichols | Kensie Coppin | Eli Hannon | Trey Nichols

Friday, Oct 2

5:00pm – Brandon Sandefur | Troy Castellano | Kat Deal

6:00pm – Dan Alley | Shane Minor | Mitch Oglesby | Mark Nesler

7:30pm – Anthony Smith | Chuck Cannon | Bob DiPiero | James Slater

9:00pm – Thompson Square | Keith Burns

THE FISH HOUSE

Thursday, Oct. 1

5:00pm – Tris Weeks | Katie Dineen | Greg Mihaly

6:00pm – Sugarcane Jane

7:00pm – Woody Bradshaw

Friday, Oct 2

6:00pm – Devan Dunlap | Goldie Lahr | Christina Crystal

7:00pm – Thom Shepherd | Coley McCabe Shepherd

8:00pm – Jacob Rice | Payton Taylor | Juliette Stewart

Saturday, Oct. 3

6:00pm – Dana Black | Jeff Silvey | Michael Magno

7:00pm– CJ Solar | Rick Huckaby | Cecilia Castleman

8:00pm – Gary Nichols | Kensie Coppin | Eli Hannon | Trey Nichols