September Is When Key West Celebrates Island Life

As summer begins to wind down across much of the country, Key West is just getting started.

September brings one of the island's most festive months, blending Labor Day celebrations, live music, waterfront events, art walks, fishing tournaments, and community traditions. The crowds remain comfortable, the ocean is still warm, and there's always something happening around town.

Whether you're planning a long weekend or you're lucky enough to call Key West home, September offers countless ways to experience the island like a local.

Here's what's happening around Key West this month.

🌴 September 2 through 6

Key West Womenfest

One of Key West's most popular annual celebrations returns for five unforgettable days.

Womenfest celebrates women through live entertainment, workshops, parties, community gatherings, and unique island experiences. This year's theme, "Lost Women in the Arts," highlights the creativity and accomplishments of women throughout history while bringing together visitors from around the world.

Whether you're attending for the first time or it's become an annual tradition, Womenfest continues to showcase the welcoming spirit that makes Key West so unique.

Dates: September 2 through 6, 2026

More Information: https://www.keywestchamber.org/latest-community-news/key-west-womenfest-returns-september-2-6-2026

🎸 September 2 through 7

3rd Annual Just a Few Friends Festival

There's no better place to celebrate Jimmy Buffett's legacy than the island that inspired so many of his songs.

The Just a Few Friends Festival returns for another Labor Day weekend filled with live music, island gatherings, storytelling, food, charity events, and celebrations honoring the life and music of Jimmy Buffett.

Festival events take place throughout Key West, bringing together Parrotheads and music lovers from across the country.

Dates: September 2 through 7, 2026

Official Website: https://www.keywesttourist.com/festivals-events/just-a-few-friends-key-west-2026/

🎶 September 2 & 3

John Frinzi & Aaron Scherz

Kick off Labor Day weekend with two of the Florida Keys' favorite singer songwriters.

John Frinzi and Aaron Scherz perform at the Key West Theater, delivering an intimate evening of storytelling, island inspired music, and the laid back atmosphere that perfectly captures the spirit of the Keys.

Dates: September 2 & 3, 2026

Location: Key West Theater

More Information: https://ourkeywest.com/key-west-events-calendar/

🇺🇸 September 3 through 7

Labor Day Weekend in Key West

Labor Day weekend is one of the biggest weekends of the year in Key West.

Throughout the island you'll find:

• Live concerts
• Waterfront parties
• Food festivals
• Running events
• Family activities
• Local entertainment
• Sunset celebrations

Whether you're spending your days on the water or exploring Duval Street, there's something happening around every corner.

Dates: September 3 through 7, 2026

More Information: https://www.keywesttourist.com/festivals-events/key-west-labor-day-weekend-2026/

🍔 September 3

Cheeseburger Beach Battle & Tribute Concert

Few things say Key West quite like a cheeseburger on the beach.

Hosted at Southernmost Beach Resort, this fun event features a beachside cheeseburger competition, live tribute music, and plenty of island vibes.

Bring your appetite and your flip flops.

Time: 5:00 PM until 8:00 PM

Official Website: https://www.keywesttourist.com/festivals-events/cheeseburger-beach-battle-concert/

🎤 September 4

Duval Street Party featuring Gary & the Landsharks

Duval Street becomes an outdoor concert venue for one of Labor Day weekend's biggest free events.

Enjoy live music from Gary & the Landsharks, dancing in the streets, food vendors, and the lively atmosphere that makes Key West famous.

Time: 5:30 PM until 9:00 PM

Location: 200 Block of Duval Street

Official Website: https://www.keywesttourist.com/festivals-events/duval-street-party-featuring-gary-the-landsharks/

🏃 September 5

Parrots & Margaritas 5K Run/Walk

Start your Labor Day weekend with a little exercise before celebrating island style.

This fun 5K welcomes runners and walkers of all ages while embracing the tropical spirit of Key West.

Whether you're chasing a personal best or simply enjoying the scenery, it's one of the most enjoyable races of the year.

Date: September 5, 2026

More Information: https://visitfloridakeys.com/plan-your-trip/plan-book/event-calendar?key%5B23%5D=23&page=2

🏊 September 5 & 6

CFK Pentathlon & Key West Open Water Swim

The beautiful waters surrounding Key West become the course for one of the area's premier swimming events.

Participants compete in multiple open water distances including:

• 800 Yard Swim
• 1 Mile Swim
• 2 Mile Swim

It's an exciting weekend for athletes and spectators alike.

Dates: September 5 & 6, 2026

More Information: https://visitfloridakeys.com/plan-your-trip/plan-book/events/cfk-pentathlon-swim-meet-key-west-open-water-swim-2026

🎷 Every Monday

Monday Night Jazz Jam

Every Monday evening, local and visiting musicians gather at the William Weech American Legion Post 168 for one of Key West's favorite live music traditions.

Expect outstanding jazz, spontaneous collaborations, and a relaxed atmosphere where every performance is a little different.

Dates:

• September 7
• September 14
• September 21
• September 28

More Information: https://visitfloridakeys.com/plan-your-trip/plan-book/events/monday-night-jazz-jams

🥬 Every Thursday

Key West Farmers Market

Every Thursday, Truman Waterfront Park becomes home to one of the island's favorite weekly traditions.

Browse:

• Fresh produce
• Local seafood
• Handmade goods
• Artisan foods
• Artwork
• Fresh flowers
• Live entertainment

It's a wonderful way to support local businesses while enjoying the waterfront.

Dates:

• September 3
• September 10
• September 17
• September 24

More Information: https://visitfloridakeys.com/plan-your-trip/plan-book/events/key-west-farmers-market-1

📚 September 17

Happy Hour with the Historian

History lovers won't want to miss this month's presentation from the Key West Art & Historical Society.

This edition explores the fascinating history of Presidents in the Florida Keys, offering stories and insights about the many presidential visits that have shaped the island's history.

Date: September 17, 2026

More Information: https://www.kwahs.org/event/hh-presidential-visits/

🎨 September 17

Walk on White

Every third Thursday, White Street transforms into one of Key West's most creative neighborhoods.

Local galleries, artist studios, boutiques, and businesses stay open late while artists showcase paintings, photography, jewelry, sculpture, and live demonstrations.

It's one of the best evenings of the month for exploring Key West's thriving arts community.

Date: September 17, 2026

Official Website: https://www.walkonwhitekeywest.com/

🎣 September 29 through October 2

IGFA Permit Invitational

One of the most respected fly fishing tournaments in the world returns to Key West.

The IGFA Permit Invitational attracts elite anglers from around the globe as they pursue one of flats fishing's most challenging species, the permit.

Even if you don't fish, watching the boats return each afternoon is worth the trip.

Dates: September 29 through October 2, 2026

More Information: https://visitfloridakeys.com/plan-your-trip/plan-book/event-calendar?category%5B77%5D=77

🎶 September 30

Gov't Mule & Ziggy Marley

Close out September with an unforgettable evening at the Coffee Butler Amphitheater.

Gov't Mule and Ziggy Marley bring their Dreaming the Same Dream Tour to Key West for what promises to be one of the biggest concerts of the fall.

The waterfront setting makes this one even more memorable.

Date: September 30, 2026

More Information: https://www.keywesttourist.com/festivals-events/

🌅 Every Single Evening

Mallory Square Sunset Celebration

No visit to Key West is complete without experiencing sunset at Mallory Square.

Every evening you'll find:

• Street performers
• Live musicians
• Local artists
• Food vendors
• Handmade crafts
• Incredible waterfront sunsets

No two sunsets are ever exactly alike, making this one of Key West's most iconic daily traditions.

Official Website: https://www.mallorysquare.com/

Who You Work With Matters

One of the things we love most about Key West is that every month brings something new to experience. From Labor Day celebrations and Jimmy Buffett tributes to art walks, live music, fishing tournaments, and waterfront sunsets, September is a wonderful time to enjoy everything that makes island life so special.

Whether you're planning your next visit or thinking about making Key West your home, understanding the lifestyle is just as important as finding the right property. As local real estate advisors, we're always happy to share our favorite events, neighborhoods, restaurants, and hidden gems that make this island unlike anywhere else.

Who You Work With Matters,

THE SPOTTSWOOD TEAM
Terri Spottswood, John Spottswood, Ted Stewart, Raymond Vazquez
305-432-4848
[email protected]
Truman & Co. Real Estate