Things to Do This Weekend in Pensacola: September 25 Through 27, 2026
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This is one of the busiest fall weekends of the year around Pensacola.
The Pensacola Seafood Festival takes over downtown for three days, the Lionfish Invitational brings another waterfront event to Plaza de Luna, athletes compete on Pensacola Beach during the Fall Beach Brawl, Gabriel Iglesias performs at the Bay Center and the Fall Big Book Sale runs all weekend.
We also worked in a few bookable experiences for anyone who wants to get on the water between events.
Here are some of the best things to do around Pensacola this weekend, September 25 through 27.
Spend the Weekend at the Pensacola Seafood Festival
Friday, September 25 through Sunday, September 27
Downtown Pensacola
Friday: 11 AM to 11 PM
Saturday: 10 AM to 11 PM
Sunday: 11 AM to 5 PM
One of downtown Pensacola’s biggest annual festivals takes over Seville Square and the surrounding parks this weekend.
The Pensacola Seafood Festival combines Gulf Coast seafood, free live music, chef demonstrations and one of Northwest Florida’s largest arts and crafts markets.
More than 150 artists and craftsmen are expected throughout the festival, while food vendors and local restaurants serve everything from fried Gulf favorites to grilled and blackened seafood.
Admission to the festival is free.
See our complete Pensacola Seafood Festival guide
Check Out the Pensacola Lionfish Invitational
Saturday, September 26 and Sunday, September 27
Plaza de Luna
Downtown Pensacola
There is another waterfront event happening alongside Seafood Festival weekend.
The FWC Pensacola Lionfish Invitational brings divers from around the region to Pensacola while also giving the public a chance to learn more about invasive lionfish and Gulf marine life.
If you are already downtown for the Seafood Festival, this is an easy additional stop along the waterfront.
Watch the Fall Pensacola Beach Brawl
Friday, September 25 through Sunday, September 27
Gulfside Pavilion
Pensacola Beach
Some of the region’s top fitness athletes are taking over Casino Beach this weekend for the Fall Pensacola Beach Brawl.
The three day competition includes elite competition Friday, individual divisions Saturday and team competition Sunday.
The event takes place around the Gulfside Pavilion, giving spectators a chance to watch the competition with Pensacola Beach as the backdrop.
Even if you are not competing, it is one of the more unique events happening on the beach this weekend.
See Gabriel Iglesias at the Pensacola Bay Center
Saturday, September 26
8 PM
Pensacola Bay Center
201 E. Gregory Street
Gabriel “Fluffy” Iglesias brings The 1976 Tour to the Pensacola Bay Center Saturday night.
The show starts at 8 PM, giving you an easy Saturday night option after spending the day downtown or on Pensacola Beach.
If you want something completely different from the festivals and outdoor events happening during the day, this is one of the weekend’s biggest ticketed events.
Dig Through the Fall Big Book Sale
Friday, September 25 through Sunday, September 27
Pensacola Library
239 N. Spring Street
Friday: 3 PM to 7 PM
Saturday: 9 AM to 5 PM
Sunday: 9 AM to 3 PM
The Friends of the West Florida Public Library Fall Big Book Sale returns downtown with thousands of used books, audiobooks, CDs and DVDs.
Prices drop as the weekend continues, with Sunday featuring the popular fill a bag sale.
This is an easy indoor stop if you are already downtown for Seafood Festival weekend.
See our guide to the Pensacola Fall Library Book Sale
Run the Pensacola Seafood 5K
Saturday, September 26
7:30 AM
Seville Quarter
130 E. Government Street
If you want to earn your Seafood Festival food before the crowds really start building, the Pensacola Seafood Don McCloskey 5K takes runners through downtown Saturday morning.
The race starts and finishes near Seville Quarter before wrapping up with a post race celebration.
It also puts you right in downtown Pensacola before the Seafood Festival gets into full swing for the day.
Get on the Water This Weekend
Available throughout the weekend
Pensacola Beach
Fall events may be taking over the calendar, but September is still very much water season on Pensacola Beach.
The Gulf and Santa Rosa Sound are still warm, summer crowds are starting to ease and you can easily work a water activity into the morning or afternoon before heading to one of the weekend’s larger events.
Go Parasailing Over Pensacola Beach
Parasailing is one of the easiest ways to add something memorable to a regular Pensacola Beach day.
Get above the water for views of the Gulf, Santa Rosa Sound and miles of white sand coastline before heading back to the beach.
Book Pensacola Beach parasailing
Rent a Jet Ski
If you would rather be driving than flying, grab a jet ski and explore Santa Rosa Sound.
A jet ski rental works especially well if you only have an hour or two open between other weekend plans and want something more active than sitting on the beach.
Book a Pensacola Beach jet ski
Take a Frisky Mermaid Dolphin Cruise
For something a little more relaxed, head out on Pensacola Bay with Frisky Mermaid.
Their dolphin sightseeing cruises give families, couples and groups a chance to look for dolphins while seeing Pensacola Beach and the surrounding waterways from the water.
Cruises typically last around 1.5 to 2 hours, making this an easy addition to a beach day without taking over your entire schedule.
Book a Frisky Mermaid dolphin cruise
Make a Weekend Out of It
You could spend almost the entire weekend downtown without running out of things to do.
Start Saturday morning with the Seafood 5K, spend the afternoon between the Seafood Festival and Lionfish Invitational, then head to the Bay Center for Gabriel Iglesias that night.
Pensacola Beach has its own major event with the Fall Beach Brawl running all three days, while the Fall Big Book Sale gives you another downtown stop throughout the weekend.
And if you want to break away from the festival crowds for a few hours, go parasailing, rent a jet ski or head out on a dolphin cruise before jumping back into the weekend events.
For more concerts, festivals and local events, check the Must Do Pensacola Events Calendar.
Looking for something you can book anytime? Browse more cruises, attractions and local experiences in our Best Things to Do in Pensacola guide.
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