Gamble Rogers Concert Series: A Guitar Outlaw Christmas

The Gamble Rogers Folk Festival has partnered with the St. Johns Cultural Council to present a monthly series of Saturday concerts at the Waterworks, from October 18, 2025, through June 20, 2026. These concerts celebrate St. Augustine's Gamble Rogers—songwriter, storyteller, guitarist, and recording artist—who taught, befriended, and performed with many of the performers on the schedule. Each concert includes two acts, one local to the region and one with national or international acclaim, usually.

In December 2025, most of the performers are well-known to locals and visitors who follow the Gamble Rogers Festival performers and organizers. Yet, this program of song and storytelling is like nothing ever seen in St. Augustine before.

A Guitar Outlaw Christmas

This is how the story goes: There was a musician from Jacksonville who moved to Seattle and did his musician thing, and met a lovely and talented lady. This musician, Chris Carlson, and an equally talented friend of his, Carl Sander, wrote a tavern opera called A Simple Love Story with Guitar Outlaws. (You can't make this up, and no, we've never heard of a tavern opera either.) Somehow, that opera was the genesis of a unique and eccentric holiday show, "A Guitar Outlaw Christmas," which they performed at the Eastlake Zoo Tavern in Seattle every year from '91, '92, or '93. (Evidently, outlaws don't keep calendars.)

And then, years later, Carlson and his very lovely and talented wife moved back to Florida and decided to gather a new bunch of ragtag musicians to resurrect or recapture or re-invent “A Guitar Outlaw Christmas,” here in the Sunshine State. And that is the December 20, 2025, concert presented as part of the Gamble Rogers Concert Series at the Waterworks. 

Whew. 

The Guitar Outlaws

If talented, funny, and thoughtful people can form a ragtag group, this is it: musicians, storytellers, singers, songwriters—folks who love everything about the holidays, and folks who have a beef with Santa and his elves.

In addition to Chris Carlson and his lovely wife, Duffy Bishop (you may have heard of her), the gang includes Don Cooper, Lon Wiliamson, Liz Williamson, Lonesome Bert, Derek Coghlan, Rusty Springfield, Katherine Archer, Alex Richman, Chris Hadjipoulos, and Chris Clark. Since we are dealing with outlaws, expect other musicians to force their way onto the stage. Some will sing songs, some will tell stories, and some will do both. You will hear their favorite things about Christmas, and their least favorite memories of the holidays, new tunes, old favorites, and a definitely different type of Christmas concert from any you've heard before.

Opening Act

Benjamin Brown, from St. Augustine, is now a student at the University of Florida. There, he focuses on two different programs: nuclear engineering and music performance on the guitar. In St. Augustine, Brown studied under Chuck Rogers, Trey Brewer, and Dr. Jonathan Dotson. 

The Details

Held at the Waterworks, a renovated historic building on San Marco Avenue, each concert is limited to 100 attendees. Advanced tickets are strongly encouraged.

Admission: $30.00 for general admission, $40.00 for seats in the first two rows. Tickets for all shows are now available. 

When: Saturday, December 20, 2025, from 7:00 to 10:00 p.m. The doors open at 6:30 p.m.

Where: St. Augustine Waterworks, 184 San Marco Avenue, St. Augustine, Florida 32084

Access to the Waterworks is through the St. Augustine Main Library parking lot. (Use 1960 North Ponce de Leon Blvd. in your GPS.) 

Built in 1898, the St. Augustine Waterworks is listed on the National Register of Historic Places. The city moved this waterworks facility to a new location after significant population growth. For a time, the building served as a community center and theater, and was later left unused. Now fully renovated again, this facility is accessible, has free parking, and yet retains its historic architectural properties and charm.

Headliners for the 2025/26 Gamble Rogers Concert Series

• Saturday, October 18, 2025—The New 76ers
• Saturday, November 22, 2025—Jordan Tice
• Saturday, December 20, 2025—A Guitar Outlaw Christmas
• Saturday, January 17, 2026—Robert Bowlin & Will Maring
• Saturday, February 21, 2026—Sunny War
• Saturday, March 21, 2026—Pat Bergeson & Bruce Forman
• In April, there will be no Waterworks concerts; the Gamble Rogers Music Festival is April 10 to 12, 2026
• Saturday, May 16, 2026—Walter Parks
• Saturday, June 20, 2026—Guy Davis

The Waterworks

Built in 1898, the St. Augustine Waterworks is listed on the National Register of Historic Places. The city moved this waterworks facility to a new location after significant population growth. For a time, the building served as a community center and theater, and was later left unused. Now fully renovated again, this facility is accessible, has free parking, and yet retains its historic architectural properties and charm.