DollyFest Key West: Dolly Parton Look-A-Like Contest

Friday, September 25, 2026. Big hair, bigger rhinestones and a $500 grand prize. DollyFest Key West brings its Dolly Parton Look-A-Like Contest to Key West, and as Dolly herself said, you'll never do a whole lot unless you're brave enough to try.

Contestants check in at 6:00 PM. Entry is $20 and there are only 20 spots, so sign up ahead through the link in the host's Instagram bio. The winner takes home $500 and a custom trophy, and Mitch Jones is MCing the whole thing.

Spectators don't need a ticket. It's first come, first served, so get there early to claim your spot, and happy hour starts at 4:00 PM. Organizers are asking the crowd to be loud for the contestants working the catwalk.

The event benefits the Friends of the Library, so a night of full-on Dolly celebration also supports a good cause.