Labor Day in Southwest Florida — 2026
Labor Day weekend is Southwest Florida's send-off to summer, with one more stretch of beach days, boat outings, and live music before the season turns. Venues up and down the Gulf Coast host cookouts, festivals, and holiday-weekend specials. Here's what's happening near you this Labor Day weekend.
Labor Day by city
Thursday, September 3
Thirsty Thursday specials every Thursday.
Learn about subjects related to Edison and Ford with Site Historians in the museum.
Join weekly chess night at the brewery to play games and enjoy craft beer.
Photography class with Kevin Boller on Thursdays from 6pm to 8pm.
A themed train ride experience titled IF ANYONE ASKS departing at 6:30pm from Fort Myers.
Mercato Nights Music Series- Powered by Porsche Naples
Enjoy live music at the Mercato Nights Music Series powered by Porsche Naples.
Rock and roll night with live music from Parks & Wreck, drink specials and dinner features.
Join us every Thursday in The Gathering. All are welcome.
Test your wits under the twinkle lights at Southern Fresh Farms Free Farm Trivia every Thursday night with cold craft brews.
Friday, September 4
Unwind with live music from Lazaro at the Beer Bar from 4-7 PM.
The historic streets of downtown Fort Myers close for the monthly Art Walk featuring over 60 artists.
Step into a slower pace and reconnect with your creativity during guided painting nights at Summer’s Art Studio & Gallery.
A live theater performance of IF ANYONE ASKS.
Hit the dance floor with live music from 8-10 PM followed by a DJ until close.
Saturday, September 5
Screwed Power Hour every Saturday.
N. Naples LARGEST Market at the Shoppes at Vanderbilt featuring fresh fruits, vegetables, seafood, honey, prepared foods and more.
On the first Saturday of every month, Collier County residents receive free zoo admission all day long.
Visit the Grumpy Goat Coffee roastery every Saturday to sample coffee from around the world with 25+ origins in stock.
Experience an afternoon of live jazz performances by the Naples Jazzmasters at the Norris Center.
Enjoy live music at the Beer Bar this Saturday from 4-7 PM.
Sit back and relax every Saturday night in the Piazza at Mercato with live local musicians.
A live theater performance of IF ANYONE ASKS.
Professional soccer match featuring FC Naples vs. Athletic Club Boise at Paradise Coast Sports Complex.
Dance the night away with live music from 8-10 PM at Seed to Table.
Join a free craft activity at the ELC every Saturday.
Sunday, September 6
Join Sunday services at Hope City Church Bonita Campus with three separate service times.
Sunday morning church services at The Cove at Paradise Coast Sports Complex.
Join the Pine Ridge Road Farmers Market on Sundays for a wide variety of products from local artisans, farmers, bakers and more.
Get two loaded tacos and one beer on tap for just $8 every Sunday at Millennial in collaboration with Tacos Los Campiones.
Country music night on the first Sunday of every month with live performances from Big Cypress and Joel Fry.
Blues and Brews feat Beautiful Bobby Blackmon
Jack's Sunday Blues Concert series presents Beautiful Bobby Blackmon.
Jack's Sunday Blues Concert series presents Memphis Lightning.
A live theater performance of IF ANYONE ASKS.
Live guitarist performance.
Watch Love Island on Sundays through Tuesdays at 9pm.
Experience raw electrifying performances with high-energy covers.
Monday, September 7
Celebrate the long Labor Day weekend with us.
Come celebrate the long Labor Day weekend with us at Jack's Seafood Bar & Grill.
Live violinist performance by Illia every Monday at Limoncello.
Kick off the week with live music at Hops & Vines from 6-9 PM.
Enjoy all-day happy hour on Mondays.
Discounts for those in the industry every Monday night.
Tuesday, September 8
Weekly morning birding walk in the Garden’s 90-acre Preserve.
Come join us every Tuesday open to close for tacos downtown and trivia.
Hear live music from talented local bands at Hops & Vines from 6-9 PM.
Monthly club meeting featuring food, guest speakers on sailing topics, camaraderie, and a themed atmosphere.
Live mandolin performance by Carlos Nunez every Tuesday at Limoncello.
Improve Spanish fluency by chatting with other adults.
Compete in trivia every Tuesday at 7pm with winners every round.
Bring the whole family for a movie night under the stars on the third Tuesday of every month at dusk.
Let creativity take center stage this summer!
Join us for Worship and Bible Study in The Hall of Tyrannus every Tuesday night.
Get personalized picks for Southwest Florida
Free GulfSider members get a weekly digest of the best events — curated for your city, no spam.