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Interested in performing at the 28th Annual Gamble Rogers Folk Festival?

The 2024 Festival will be returning to the St. Johns County Fairgrounds located at
5840 FL-207 E, Elkton, FL 32033.


Submit your application to perform on April 12 - 14th, 2024!



Join us under the Oak trees at the Colonial Oak Music Park on Sunday afternoons during Sing Out Loud for a special Gamble Rogers Festival Showcase taking place on September 10th, 17th, and 24th! Event starts at 3:00pm, doors open at 2:00pm 

The Colonial Oak Music Park is an outdoor venue at 21 Saint George Street , St. Augustine, Florida 32084 in Historic downtown St. Augustine, FL. This "community music park" is located under a majestic 300 year old oak tree surrounded by picnic tables, offering free live music as well as food and drinks for purchase.


Sunday, September 10th

3:00pm The Dunehoppers
4:15pm The Skinny
5:30pm Big Pineapple
6:45pm Aslyn & The Naysayer
8:00pm John Dickie & Collapsible B

Sunday, September 17th

3:00pm Skin & Bonz
4:15pm The Taildraggers
5:30pm The Thick & Thin String Band
6:45pm Wild Shiners
8:00pm Grant Peeples

Sunday, September 24th

3:00pm Jim Carrick & Charley Simmons
4:15pm Lee Hunter & Joey Kerr
5:30pm Marianne Lerbs
6:45pm John Winters & Mark Richey
8:00pm Charlie Robertson


Second Annual


Join us at the St. Johns County Agricultural Center on October 7, 2023 for a special event featuring John Dickie with Collapsible B.

Tickets are $35 each and can be purchased through Paypal button below.

If you would like to make a contribution please download and complete the form below and return to any Gala volunteer, or send to:
Lolly Rogers, Gala Chair, 43 Florida Avenue, St. Augustine, FL 32084 OR email to:

The Second Annual Gamble Gala, a fundraiser for the Gamble Rogers Folk Festival, is now selling tickets for their exciting raffle prize trip. This year, the winner will be treated to a stay in historic Winter Park, Florida, where Gamble Rogers grew up. Dubbed the “Gamble Ramble”, the prize includes a $1000 gift certificate to the luxurious Alfond Inn, 2 passes to the Morse Museum, and 2 tickets to the popular Winter Park Scenic Boat Tour.


The Alfond Inn is an easy walk from downtown Winter Park, where there are many more shops, restaurants, and more. Tour Rollins College campus, or visit Casa Feliz, designed by renowned architect James Gamble Rogers II.


Raffle tickets are $5 each, or $20 for 5 tickets. They can be purchased in person at the Sing Out Loud stage at Colonial Quarter on 9/17 and 9/24, as well as at the St. Augustine Farmer's Market on 9/30 and during the Gala on 10/7. Come see us to purchase tickets and enter for a chance to win this amazing getaway package!!!


Can’t make it to buy raffle tickets at one of the in person events? Purchase through PayPal using the button below. You do not need to be present at the Gala to win!

Gamble Ramble


Gamble Rogers Concert Series
Live From The Waterworks

OCTOBER 21, 2023

The Driftwoods featuring Christian Ward with The Taildraggers

NOVEMBER 18, 2023

Jordan Tice with Noan Partly

DECEMBER 16, 2023

John Paul White with Hadley Parrish-Cotton

VENUE: The Waterworks ~ 184 San Marco Avenue St. Augustine, FL 32084. Doors at 6:00pm, music at 7:00pm. Libations are available for purchase.


Check out photos from the 2023 Gamble Rogers Folk Festival

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