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Pensacola Pickles and Wings Run 2027

Pensacola Pickles and Wings Run 2027

calendar_today May 15, 2027 location_on 211 Bayfront Pkwy, Pensacola, North Florida 32502

About This Event

It is kind of a Big Dill.

The Pensacola Pickles and Wings Run is a costumed fun run and walk that kicks off the Pensacola Pickles and Wings Family Festival at historic Bartram Park in downtown Pensacola.

This is not a race. Nothing is timed. Pick your distance, put on a costume, and walk or run with a few hundred people dressed as pickles.

Pick a side at registration, Team Pickle or Team Wing, and come dressed for it.

Every registration includes a bib and a ribbon at the finish. Water is provided on course and at the finish. Bring your own costume, that is the whole point. We do not sell them.

The games, contests and all the rest happen at the festival, not at the run.

DISTANCES

1 Mile Family Walk. One easy loop through the historic district. Stroller and wagon friendly.

2 Mile Run or Walk. A loop through historic downtown Pensacola. Run it, walk it, or somewhere in between.

4 Mile Run. The downtown loop extended along the waterfront. Please note this distance is for runners. The course closes at 8:30 AM and walkers will not finish in time. Choose the 2 Mile if you plan to walk.

All three start and finish at Bartram Park, 211 Bayfront Pkwy. The course runs on open public streets that are not closed to traffic. Obey all traffic signals and follow the instructions of course marshals.

PRICING

Ages 13 and up: $25 through February 28, $30 March 1 through April 15, $35 April 16 through May 9. Ages 12 and under: $10 at every window.

Registration closes Sunday, May 9. All participants must be pre registered. There is no event morning registration.

BIB PICKUP

Monday, May 10 through Thursday, May 13, 11:00 AM to 4:00 PM 221 E Government Street, Pensacola, FL 32502

Bring your registration confirmation. A friend can pick up for you if their name is on the list. Registering a group? One person can collect all the bibs.

Ribbons are handed out at the finish line, not at pickup.

Cannot make it during the week? Will call is available at Bartram Park on event morning, 6:45 to 7:25 AM, for pre registered participants only.

EVENT MORNING, SATURDAY MAY 15

6:45 AM   Will call opens at Bartram Park, pre registered only 7:15 AM   Suggested arrival. Find parking and get in costume. 7:30 AM   Group costume photo at the start line 7:35 AM   Route overview and welcome 7:40 AM   Start, all distances together 8:00 AM   Finishers in, ribbons at the finish line 8:30 AM   Event concludes

Plan to arrive by 7:15. Downtown parking fills up and the group photo starts at 7:30 sharp. Park in downtown street parking or public lots near Bartram Park.

QUESTIONS

Do I have to run? No. Walk any distance you like. Is it timed? No. No timing, no results, no age group awards. Can I register on event morning? No. Registration closes May 9. Do I get a shirt? No. You get a bib and a ribbon. We keep it simple so we can keep it affordable. Where are the games and contests? At the festival, starting at 10 AM. Can I bring a stroller? Yes. The 1 Mile Family Walk is stroller and wagon friendly. Is it refundable? No. All entry fees are non-refundable and bibs are non-transferable.

AFTER THE RUN

Stay downtown. The Pensacola Pickles and Wings Family Festival opens at 10 AM with wings, pickles, food trucks, live entertainment, carnival games and a kids zone across Seville Square, Fountain Park and Bartram Park, Saturday and Sunday, free admission.

A portion of the proceeds benefits the Ronald McDonald House of Northwest Florida, supporting families with children receiving medical care.

More at pensacolafest.com 850-941-4321

Weather

Frequently Asked Questions

When is Pensacola Pickles and Wings Run 2027 2027?
Pensacola Pickles and Wings Run 2027 takes place on Saturday, May 15, 2027 in Pensacola, Florida.
Where does Pensacola Pickles and Wings Run 2027 take place?
Pensacola Pickles and Wings Run 2027 is held at 211 Bayfront Pkwy in Pensacola, Florida (North Florida). See the course maps section on this page for route details where available.
How do I register for Pensacola Pickles and Wings Run 2027?
Registration is online — use the Register button on this page to sign up through the race's official registration page. Registering early usually means lower entry fees.
Is there a promo code for Pensacola Pickles and Wings Run 2027?
Discounts are set by the race organizer and appear on the official registration page when active. The most reliable way to pay less is registering early — most Florida races raise prices as race day gets closer.

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calendar_today May 15, 2027
location_on 211 Bayfront Pkwy, Pensacola, North Florida 32502
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Pensacola Pickles and Wings Run 2027

May 15, 2027

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