Key West Chick Fest 2026 - Sunset Pier & Kaya Island Eats

Sunset Pier & Kaya Island Eats’ Backyard Bar Present the 5th Annual Key West Chick Fest

Key West Chick Fest 2026 returns January 14–18, 2026, transforming Sunset Pier and Kaya Island Eats’ Backyard Bar into the epicenter of Southern-rooted songwriting, Americana soul, and country storytelling. Now in its fifth year, this celebrated female singer-songwriter festival in Key West showcases an all-star lineup of rising and award-winning artists from Nashville, Texas, the Carolinas, and beyond—curated and hosted by TRMA Female Artist of the Year Erica Sunshine Lee.

Blending island energy with authentic country and Americana voices, the festival spans five days of live performances, songwriter showcases, collaborative sets, and a full-band finale. Performances take place during sunset hours at Sunset Pier, followed by intimate evening showcases at Kaya Island Eats’ Backyard Bar, creating a walkable, music-filled experience at the Southernmost Point.

The 2026 artist lineup features Erica Sunshine Lee, Billie Jo, Paige King Johnson, Kaitlyn Croker, Hillary Reese, Betsy Franck, Meredith Crawford, Bailey Rae, and Morgan Lee Powers—each bringing a distinct voice shaped by traditional country roots, modern storytelling, and Americana grit. Highlights include the Kickoff Party on January 14, rotating nightly showcases January 15–17, a Songwriter Brunch Showcase on January 18, and the Finale Full Band Show at General Horseplay with $20 admission at the door.

Founded as a creative platform to elevate women in songwriting, Key West Chick Fest has become a nationally recognized destination event—part writers’ retreat, part live music festival—set against the unmistakable backdrop of Key West’s waterfront stages.

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