EVENT DETAILS
Pensacola knows how to throw a party.
May 16th, 2026, is our loud, delicious, family-friendly love letter to downtown—and to pickles and wings. We're turning Seville Square into a full-day festival experience packed with food trucks, craft vendors, local artists, small businesses, live entertainment featuring singers, dancers, poets, and more, a pickle-eating contest, costume competitions, and a kids zone with carnival games that'll keep the little ones busy while you focus on your next plate.
This isn't a fancy food festival. It's a neighborhood party with really good food. Wings you'll dream about. Pickle creations in places you never expected—from pickle ice cream to pickle pizza to pickle-brined everything. Entertainment that keeps your feet moving. A pickle-eating contest that'll have you cheering. Costume contests that'll have you laughing. And all of it surrounded by the charm, history, and walkable energy of historic downtown Pensacola.
Supporting the community is a core part of this event. A portion of the proceeds from the Pensacola Pickles and Wings Family Festival will be donated to the Ronald McDonald House of Northwest Florida, helping support families with children receiving medical care in our region. Come hungry, come local, and come ready to celebrate food, fun, and giving back together.
This is the pickle party Pensacola didn't know it needed. Come find out what all the dill is about.
The Pickle Priest
Special Guest
EVENTS SCHEDULES
Seville Square Gazebo Stage Schedule:
10:00 AM -- Open
10:00 AM - 8:00 PM -- Food Truck Alley, Pickle Marketplace, Kids Zone & Carnival Games Open All Day
11:00 AM -- Gazebo Stage Live Performance by Tyler Morrison (Country/ Rock/Gospel music)
12:00 PM -- Gazebo Stage Live Performance by Rockstar Girlfriend(Rock & R &B)
1:00 PM -- Gazebo Stage Live Performance by Lafayee (R &B)
1:30 -- Wing Challenge Gazebo Area hosted by Hungry Brothers
2:00 PM -- Gazebo Area Kids & Adult Costume Contest (Pickle & Wing Themed!)
Meet Pensacola's new brand Ambassadors Dinosaurus Parker and Rex
3:00 PM -- Gazebo Stage Live Performance by Brennan Lowery Music (Country)
3:00 PM -- KREWE Gauntlet by KREWE OF CHEERS
4:00 PM -- Gazebo Area Adult Pickle Eating Contest
4:30 The Chicken Nugget Crew of Perdido Performing Arts (Hip Hop Dance)
5:00 PM -- Gazebo Stage Live Performance by Dee and the Stray Cat Bluesmen (Old School Chicago Blues)
6:00 PM -- Gazebo Stage Live Performance by Cherry Bomb and Password Reset Classic Rock/ R&B)
Gazebo Stage Live Performance by Sara Sol Flame & Rayah Sunshine (Circus-LED Hoop Artists)
8:00 PM -- Festival Closes
Fountain Park Children's Fun Zone Schedule
10:00 AM - 6:00 PM
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🎨 Face painting
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🖍️ Arts and crafts station
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🎪 Carnival games
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🫧 Bubble station
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🏛️ Pensacola Parks and Recreation Booth
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🏰 Bounce houses
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✨ And more!
Bartram Park Stage Schedule:
10:00 AM -- Open
10:00 AM - 8:00 PM -- Food Truck Alley, Pickle Marketplace, Kids Zone & Carnival Games Open All Day
11:00 AM -- Bartram Park Stage Live Performance by Tba
12:00 PM -- Bartram Park Stage Live Performance by Teddy Sasse (Americana/ Rock/ Country)
1:00 PM -- Bartram Park Stage Live Performance by Lost Localz (Country/ Classic Rock/ R&B)
3:00 -- Bartram Park Stage Live Performance by Billy Bones (Rock, R & B, Country, Jazz, Pop, and More)
4:00 PM -- War Zone Music Artists SargI, XTK, Hitman93 (Rap | Hip-Hop)
5:00 PM -- Bartram Park Stage Live Performance by Tuffalo & the TreeWalkers (Rock/Reggae/Blues/Folk)
6:00 PM -- Bartram Park Stage Live Performance by WYNTER (Classic Metal/ 70's & 80's Rock)
8:00 PM -- Festival Closes
THE LEGENDARY PICKLE PRIEST🥒⚔️
Pickle Priest Experience, Get Your Pickles Blessed!
A larger-than-life guest is arriving at the Pensacola Pickles and Wings Family Festival, and you will not want to miss him. The legendary Pickle Priest is making a special appearance, bringing laughs, unforgettable photo opportunities, and a one-of-a-kind festival experience.
Stop by the Pickle Priest booth throughout the day, where he will be selling his famous pickles, exclusive merchandise, and signing autographs for fans. Whether you are a pickle superfan or just love quirky festival moments, this is your chance to meet one of the event’s most talked-about personalities.
TIME:
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10:00 to 8:00 PM Vendor Marketplace at Seville Square
EXPERIENCE INCLUDES:
Fresh pickles available for purchase
Official Pickle Priest merchandise
Autograph opportunities
Photos with the Pickle Priest
PARKER AND REX 🦖🌴
Meet Pensacola’s Dino Ambassadors of Fun!
Two larger than life guests are stomping into the Pensacola Pickles and Wings Family Festival, and you will not want to miss them. Meet Parker and Rex, the crowd favorite dinosaur ambassadors from Pensacola Parks and Recreation. These prehistoric pals bring big smiles, high fives, and unforgettable photo moments for kids and families all day long.
Stop by when Parker and Rex roam through the festival grounds at Seville Square. They will be greeting guests, posing for photos, giving high fives, and helping make this family festival a ROARing good time for everyone.
TIME:
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TBA
EXPERIENCE INCLUDES:
High fives from Parker and Rex
Photo opportunities with the dinosaurs
Fun meet and greet moments for kids and families
Roaming dinosaur appearances throughout the festival
Pickle Ride "It's a Big Deal"
The Dill Is to Stay On
The Mechanical Pickle Ride is one of the festival’s most popular attractions, giving guests the chance to hop on and test their balance, skill, and bravery. Riders take on a spinning, bucking pickle while friends and family cheer them on. It is fun, fast-paced, and a crowd favorite for all ages.
TIME:
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10:00 to 8:00 PM at the Bartram Park
REGISTRATION:
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On-site sign-up at the Pickle Ride booth. Waivers are required prior to riding.
RIDE FEE:
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$TBA
RULES:
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Waivers required
Must follow operator instructions
Closed-toe shoes recommended
Height and weight restrictions may apply
COSTUME CONTEST — DRESS TO IMPRESS!
Show off your creativity and win BIG! Our Costume Contest celebrates the most dill-ightful, wing-tastic, and outrageously creative outfits at the festival!
Whether you come dressed as a giant pickle, a saucy chicken wing, a jar of brine, or something wildly original—we want to see it! This is your chance to strut your stuff on the main stage and compete for amazing prizes. We have separate contests for adults and children, so the whole family can join the fun!
ADULT COSTUME CONTEST (Ages 18+)
TIME:
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1:00 PM on the Main Stage
REGISTRATION:
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Sign up at the Contest Booth starting at 10 AM
ENTRY:
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FREE to enter
CASH PRIZES:
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🥇 GRAND PRIZE (1st Place): $300 CASH
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🥈 2nd Place: $200 CASH
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🥉 3rd Place: $100 CASH
🧒 CHILDREN'S COSTUME CONTEST (Ages 12 & Under)
TIME:
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2:00 PM on the Main Stage
ENTRY:
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FREE to enter
PRIZES & TROPHIES:
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🥇 1st Place: Trophy + Prize Pack
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🥈 2nd Place: Trophy + Prize Pack
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🥉 3rd Place: Trophy + Prize Pack
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⭐ All participants receive a special ribbon!
PICKLE EATING CONTEST
Think you can handle it? It's time to prove you're the real dill!
Get ready for Pensacola's most epic pickle showdown! Our Pickle Eating Contest brings together brave competitors to see who can devour the most pickles in record time. It's messy. It's briny. It's absolutely hilarious. And it could be your moment of glory.
TIME:
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4:00 PM on the Main Stage
REGISTRATION:
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Sign up at the Contest Booth starting at 10 AM (limited spots!)
ENTRY FEE:
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$20
PRIZES:
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Bragging rights + prizes for 1st, 2nd, and 3rd place
RULES:
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Participants must be 18+ | Waivers required | No outside pickles allowed | No professional or competitive eaters
VENDOR LAYOUT
We’ve officially dropped the vendor layout and it’s packed from end to end
From local favorites to must try bites, unique finds, and nonstop energy all throughout Seville Square… this is where you come to explore, taste, shop, and discover
Every turn brings something new, so come ready to walk, snack, and repeat 😎
🔥 FOOD TRUCKS & VENDORS — WE STILL HAVE LIMITED SPACE AVAILABLE
Want your business in front of thousands
Now’s your chance to get in on the action
TIME:
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10:00 to 8:00 PM
FOOD TRUCKS & VENDORS: — WE STILL HAVE LIMITED SPACE AVAILABLE
Now’s your chance to get in on the action!!
