Guide to Family-Friendly Fall Festivals



Summers on the Gulf Coast are beautiful and filled with lots of fun, but with the crisp, cooler weather comes a new type of fun- the fall festivals! And boy are they back!

Beginning in October, there seems to be some type of community event (or multiple) occurring every weekend, but below we have your guide to the family-friendly festivals to round out your year.

Family-Friendly Fall Festivals 

August Festivals

14th- Waterfest Milton  (5158 Willing Street-Jernigan’s Landing) 10:00- 3:00

From 10am to 3pm join in the fun with the waterslides, bounce houses, games, food trucks, and giveaways. The entire event is free for children 12 and under and is a great send-off to the summer!

Tip:  Blankets, coolers, and chairs are welcome, but no glass, please.  

September Festivals

festivals24th-26th Seafood Festival– (Seville Square)

Yes, the food and music are always enjoyable, and not to mention the amazing vendors featuring their arts and crafts, but the children’s tent is equally as fun for our littles and there is even a 5K!

You can start your Saturday by participating in the fun 3.1-mile event as a family then celebrate with shopping and eating! The children’s area not only includes face painting and crafts but also giveaways. 

And while you are making your next purchase for that bare wall in your home, there are also vendors specifically for the children with superhero gear, local children’s authors, and more.  

October Festivals

9th- 7th Annual Pensacola Dragon Boat Festival (Bayview Park)

Benefitting Gulf Coast Kid’s House, this event is a huge team-builder for various companies and organizations throughout the community.

Teams begin racing at 9 AM, but the vendors and kids’ activities will begin an hour prior.  There is a DJ, arts and craft booths, and face painting and games for the kids. It is a great day in Bayview Park!

9th-10th- Munson Heritage Festival (Krul Lake Recreational Area)

History comes to life for two days with food and local arts and crafts highlighting the culture of the area’s past as well as celebrating the beautiful nature surrounding Munson. 

There is also a Trail Ride and Saturday night camp.  

Tip: This is a cash-only event. 

17th- Food Truck Festival (Vince Whibbs Sr Community Maritime Park)

What is better than another whole festival centered around food? 

How about adding live music and entertainment for the kids in the form of a bounce house, but also adding in the bonus of knowing a portion of proceeds go to Feeding the Gulf Coast?

Tip- There is a $2 entry fee for anyone 13 and older.

November/December Festivals

5-7- Great Gulf Coast Arts Festival (Seville Square)

Photo courtesy of Visit Pensacola

Pensacola is home to this premier and well-regarded event each Fall. The three-day festival features hundreds of artists, live musicians, performing arts, food vendors, a student art exhibit, and its own Children’s Art Festival.

In Bartram Park, there is free kids-crafts-galore with masks, wands, capes, buttons, clay, flowers, and more. 

I particularly enjoy this event for the focus on emerging student artists and performers as well as Very Special Arts Day- the Friday event for special needs students in both Escambia and Santa Rosa Counties. 

Tip- This is mostly a daytime event with the Children’s area operating 10-4 and the event itself closing each evening at 5.  

November 26- December 24- Winterfest!  (Palafox Plaza)

Photo courtesy of Visit Pensacola

Snow in Pensacola?! YES! Winterfest begins with the Elf Parade kick-off on November 26th (Black Friday) at 4:30 if attending, but a 3:30 lineup if participating. 

YES, PARTICIPATING! You can be in the parade!

There are prizes for the best ugly sweater, stroller, wagon, elf ears, and more. When the parade ends, the official Holiday season in Downtown Pensacola begins with the lighting and the arrival of Jolly Ol’ St. Nick. 

Winterfest will take place weekend nights thereafter, but nightly beginning December 21.  There is a free street show, but also various tours such as Polar Express, Grinch Tour, Scrooge, and Cajun Christmas available with ticket purchases.

AND YES, SANTA IS BACK! Visit with Father Christmas on his sleigh in the middle of Wonderland Plaza. Photos are also available for purchase. 

Tip: Get your tickets for tours and photos EARLY! Visit the Winterfest website for information and pricing. 

For more local events occurring throughout the year, please be sure to check the PMC calendar on our website!


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