Upcoming Events in Key West

Upcoming Events in Key West: A Weekend of Festivals, Fun, and More!

Looking for the perfect way to spend your weekend and beyond in Key West? You're in luck! The island is buzzing with exciting events that capture the unique spirit of the Conch Republic. From art exhibits to live music, epicurean delights, and running events, there’s something for everyone to enjoy. Here's a glimpse into what’s happening this weekend and in the coming weeks.

Sunset Celebration at Mallory Square

January 1 - December 31, 2024
Mallory Square, 400 Wall Street, Key West, FL 33040

Key West is renowned for its breathtaking sunsets, and there's no better place to catch them than Mallory Square. Every evening, two hours before the sun dips below the horizon, the square comes alive with street performers, artisans, and food vendors, all celebrating the day’s end in true Key West style. It’s a year-round tradition that never gets old!

Key West Art & Historical Society: Beaches, Creatures & Cowboys - Florida Movie Posters Exhibit Opening

 May 31 - September 1, 2024
Customs House Museum, 281 Front St, Key West, FL 33040

Immerse yourself in a slice of cinematic history with this unique exhibit at the Customs House Museum. "Beaches, Creatures & Cowboys" showcases a vibrant collection of Florida-themed movie posters, capturing the Sunshine State's diverse landscapes and quirky characters. Whether you're a film buff or just looking for a cool, air-conditioned activity, this exhibit is a must-see.

Just a Few Friends: Key West Favorite Son Celebration

 August 30 - September 2, 2024
 Various Locations, Key West, FL 33040

This weekend, Key West rolls out the red carpet for its hometown heroes with the "Just a Few Friends" celebration. Expect a mix of intimate gatherings, live music, and local stories, all honoring the island's favorite sons. It’s a perfect way to experience the close-knit community vibe that makes Key West so special.

Key West BrewFest

August 30 - September 1, 2024

 Various Locations, Key West, FL 33040

Beer lovers, rejoice! The Key West BrewFest is back, and it’s bigger and better than ever. Over 200 beers are on tap from local and international breweries, with tastings, seminars, and special events happening all weekend long. Raise a glass to the island’s laid-back lifestyle while enjoying some of the best brews the world has to offer.

Cheeseburger Beach Battle & Concert

August 30, 2024, 4:00 PM
Southernmost Beach Resort, 1319 Duval St, Key West, FL 33040

Get ready for a battle of epic proportions – the Cheeseburger Beach Battle! This fun and flavorful event pits local chefs against each other to create the ultimate cheeseburger. After you've had your fill, stick around for a live concert that’s sure to keep the good vibes going well into the evening.

Parrots and Margaritas 5K Run/Walk or the Flip-Flop Mile

 August 31, 2024, 8:00 AM
 Irish Kevin's Bar, 211 Duval St, Key West, FL 33040

Kick off your Saturday morning with a tropical twist! The Parrots and Margaritas 5K Run/Walk is a fun way to stay active while embracing the island's festive spirit. If a full 5K sounds like too much, opt for the Flip-Flop Mile instead. Either way, you'll earn your margarita – or two – when you cross the finish line.

Poolside Juried Show by JAG Gallery

 August 31, 2024, 5:00 PM
 JAG Gallery, 1075 Duval Street, Duval Square C23, Key West, FL 33040

Art lovers won’t want to miss this! The Poolside Juried Show at JAG Gallery features works from some of the island's most talented artists, all showcased in a laid-back, poolside setting. Sip on a cocktail, browse the art, and maybe even take home a piece of Key West’s creative spirit.

Coffee Butler Amphitheater: Aaron Lewis with Mikey Wayne

 August 31, 2024, 7:00 PM
 Coffee Butler Amphitheater, 21 Quay Rd, Key West, FL 33040

Wrap up your Saturday with some live music under the stars at the Coffee Butler Amphitheater. Country music star Aaron Lewis takes the stage, with Mikey Wayne opening the show. This is your chance to enjoy an unforgettable night of music in one of the island’s most iconic venues.

It's-5-o’clock in Key West: A Celebration of Jimmy Buffett

 September 1, 2024, 12:00 AM
 Duval St, Key West, FL 33040

Calling all Parrotheads! Celebrate the music and legacy of the legendary Jimmy Buffett with a special event on Duval Street. Expect a day (and night) filled with margaritas, live music, and, of course, a whole lot of laid-back island vibes. It’s the ultimate way to honor the man who made "island escapism" a way of life.

Fantasy Fest: Meet The Candidates

 September 6, 2024, 6:30 PM
 Key West Theater, 512 Eaton St, Key West, FL 33040

As Fantasy Fest approaches, get to know the candidates vying for the title of King and Queen of this legendary event. The "Meet The Candidates" night at Key West Theater is your chance to see the creativity and charisma that these hopefuls bring to the table. It’s the start of the journey to one of Key West's most anticipated annual celebrations.

Awaken: The Music of YES

 September 7, 2024, 8:00 PM
 Key West Theater, 512 Eaton St, Key West, FL 33040

Relive the magic of progressive rock with "Awaken: The Music of YES" at the Key West Theater. This tribute band brings the legendary music of YES to life, delivering a performance that’s sure to resonate with fans old and new. Don’t miss this chance to experience the timeless tunes that defined an era.

Pokey LaFarge

 September 15, 2024, 8:00 PM
 Key West Theater, 512 Eaton St, Key West, FL 33040

Pokey LaFarge is set to bring his unique blend of Americana, blues, and folk to the Key West Theater. With a sound that’s both nostalgic and fresh, LaFarge’s music is perfect for a laid-back evening on the island. Grab your tickets early – this is one show you won’t want to miss.

Final Key West Paddle Classic

 September 28, 2024, 6:00 AM
Higgs Beach, Key West, FL 33040

The Final Key West Paddle Classic is your last chance to experience this thrilling paddleboard race. Set against the stunning backdrop of Higgs Beach, this event attracts paddlers from all over the world. Whether you're competing or cheering from the shore, it’s a spectacular way to spend a morning in Key West.

There’s no shortage of things to do in Key West, and this lineup of events ensures your days and nights are packed with fun, culture, and a true taste of the island’s eclectic charm. For more details and even more events, be sure to visit Key West Tourist.

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