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About this market
Pensacola Pickles and Wings Family Festival 2027 Pickles, wings, food trucks, live music, contests, vendors and family fun in historic downtown Pensacola! FREE admission and all ages welcome. The Pensacola Pickles and Wings Family Festival returns May 15 & 16, 2027, for TWO full days of food and fun at Seville Square, Fountain Park and Bartram Park in Downtown Pensacola, Florida. After welcoming more than 5,000 attendees to our inaugural festival, we're coming back bigger for 2027! EVENT DETAILS May 15 & 16, 2027 10 AM to 7 PM Daily Seville Square, Fountain Park & Bartram Park Downtown Pensacola, Florida FREE Admission • All Ages • Rain or Shine WHAT TO EXPECT 🥒 The Pickle Priest Meet the viral TikTok favorite for pickle blessings, photos and plenty of laughs. 🍗 Best Wings of Pensacola Challenge Local restaurants and wing vendors compete to see who will take home the title. 🔥 Mechanical Pickle Climb aboard the giant bucking Mechanical Pickle and see how long you can hang on. 🥒 Pickle Eating Contests Children's and adult pickle eating competitions with prizes and bragging rights. 🎭 Pickle & Wing Costume Contests Come dressed as your favorite pickle, wing or food inspired creation. 🎵 Live Music & Entertainment Bands, musicians, performers, special guests and interactive entertainment throughout the weekend. 🍗 Wings & Food Trucks Enjoy traditional, hot, smoked, sweet, savory and creative wings plus food trucks and specialty foods. 🥒 Pickle Paradise Gourmet pickles, fried pickles, pickle foods, snacks, specialty products and pickle merchandise. 🛍️ Vendor Marketplace Shop local and regional artists, makers, crafters, retailers and specialty businesses. 🎈 Kids & Family Fun Games, activities, attractions, characters, entertainment and photo opportunities for the whole family. MAKE IT A PENSACOLA WEEKEND It's a Big Dill... Stay • Play • Vacay! Come for the festival and spend the weekend exploring Pensacola's sugar white beaches, historic downtown, restaurants, shopping, nightlife, attractions and waterfront. A CAUSE WE LOVE A portion of festival proceeds benefits Ronald McDonald House Charities of Northwest Florida, supporting families with children receiving medical care. VENDORS, FOOD TRUCKS, ENTERTAINERS & SPONSORS Applications are now open for: Wing Vendors • Pickle Vendors • Food Trucks • Marketplace Vendors • Artists & Crafters • Retail Vendors • Musicians • Entertainers • Attractions • Sponsors • Community Partners Food vendors and food trucks must offer at least one pickle themed menu item. Pensacola Pickles and Wings Family Festival May 15 & 16, 2027 Downtown Pensacola, Florida