Pensacola Pickles and Wings Family Festival

Pensacola History and Haunting Tours and Events is proud to announce the inaugural Pensacola Pickles and Wings Family Festival, a free-admission celebration of food, entertainment, and community taking place on Saturday, May 16, 2026, from 10 AM to 8 PM at historic Seville Square in downtown Pensacola.

The festival promises a full day of family-friendly fun featuring wings, pickles, food trucks, craft vendors, costume contests with cash prizes, a pickle eating contest, a kids zone with carnival games, and live entertainment all day long on THE GRAND BRINE & SAUCED STAGE.

“It’s Kind of a Big Dill,” says the festival’s tagline — and organizers are expecting thousands of attendees to gather under the centuries-old oak trees of Seville Square for Pensacola’s newest tradition.

THE GRAND BRINE & SAUCED STAGE — Local Entertainment All Day

The festival’s main stage will showcase local talent throughout the day, featuring singers, dancers, poets, spoken word artists, acoustic performers, and more. Local entertainers interested in performing can apply by downloading the entertainer application packet at pensacolafest.com. There is no fee to perform.

Supporting the Community: A portion of proceeds from the Pensacola Pickles and Wings Family Festival will benefit the Ronald McDonald House of Northwest Florida, supporting families with children receiving medical treatment.

Get Involved: Vendor opportunities, food truck applications, sponsorship packages, and entertainer applications are now available. Visit pensacolafest.com or call (850) 941-4321 for more information.