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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 Book Cover.jpeg

A Troubadour's Life


Beloved raconteur, environmentalist, and down-home philosopher, Gamble Rogers (1937–1991) ushered in a renaissance of folk music to a place and time that desperately needed it. In this book, Bruce Horovitz tells the story of how Rogers infused Florida's rapidly commercializing landscape with a refreshing dose of homegrown authenticity and how his distinctive music and personality touched the nation.

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