Key West Labor Day Weekend 2022 Picks

This Labor Day, Monday, Sept. 5, 2022, concerts, festivals, and activities abound in the land of sunshine and warm weather. Give summer a proper send off, bask in the fruits of your labor, and enjoy the best entertainment the island has to offer. Here are events to look forward to on the long Labor Day weekend in Key West.

Live Music

Daily at select locations around Key West

Labor Day weekend 2022 in Key West is packed with live musical performances. Places like Green Parrot, Sloppy Joe’s, and Smokin’ Tuna Saloon always have stellar local acts, and musicians Dani Hoy, Derek Dunbar, and The Cayo Hueso Riot are already slated to perform at places like Off the Hook Grill and The Bull & Whistle Bar. Read up on more of the best places in Key West for live music here. When you stay with 24 North Hotel, you don’t have far to go for entertainment. Our on-site Republica Bar & Lounge features live music every night of the week.

Key West BrewFest

Sept. 1 - 5 at various locations in Key West

BrewFest is back! It’s the 11th iteration of the craft beer festival featuring pool parties, food and beer pairings, tasting festivals, and more. Catch one of the many events through Sept. 1 - 5, with the main event - the tasting festival - set for Saturday, Sept. 3. For details, check out our Complete Guide to BrewFest 2022.

Historic Seaport Food & Cultural Walking Tour

Daily at Historic Seaport, Key West

The 1.3-mile long food walking tour covers six local restaurants in the charming Historic Seaport with a focus on seafood. You’ll discover hidden gems and get a history lesson in the process. Tastings include fresh, local catch, Key West pink shrimp, spiny lobster, and more from places like Garbo’s Grill, Bagatelle, and Eaton Street Seafood Market. All ages are welcome. Reserve tickets ahead of time.

Mallory Square Sunset Celebration

Daily at Mallory Square, Key West

Salute the end of the summer season by joining the Sunset Celebration at Mallory Square. The communal gathering has been a Key West staple since the 1960s! Watch the sun dip below the horizon alongside live music, jugglers, and other live acts working the crowd. If you’re lucky you may even spot the “green flash.”

Mel Fisher Days

Sept. 2, 3, 4, and 5 at select locations around Key West

The annual festival returns to celebrate the beloved Key West treasure hunter with full days of festivities planned around the island. This year also marks a very special occasion - it’s the 400th anniversary of the final voyage of the Spanish galleon Nuestra Señora de Atocha - Mel Fisher’s biggest discovery. Mel Fisher Days events include book signings from treasure hunting authors, the 400th Commemoration Speakers Symposium, and the Mel Fisher Days Charity Event at Schooner Wharf Bar.

University of Miami vs. Bethune-Cookman University

Sept. 3, live on ACCN

College football is back! Watch the University of Miami take on Daytona Beach’s Bethune-Cookman University from Hard Rock Stadium in the season opener. The island’s sports bars like Sandbar Sports Grill, Jack Flats, and Shooterz Lounge and Sports Bar are all likely to have the game on. Kickoff is at 3:30 p.m.

Scavenger Hunt Adventure

Sept. 5 at Old Town, Key West

Guided by any smartphone, teams solve clues and complete challenges while discovering Key West. This is a fun activity for the whole family. Start anytime after 8 a.m. and play at your own pace on Labor Day. Get your tickets here.

Reality is a Drag Show

Sept. 5 at Aqua Bar and Nightclub

Join Aqua’s resident queens at 9 p.m. for a raucous end to the weekend. Expect a fun, hilarious show that attracts a diverse audience for a night of delicious drinks and light-heartedness. Reserve your table in advance.

Book your final trip of the summer with 24 North Hotel and enjoy deals just for being a Floridian.

That’s right! Take advantage of the Florida Residents package at 24 North Hotel in Key West to save up to 20% off your nightly rate, plus 50% off our Resort Fee. We have a host of amenities that set us apart from the rest, such as shuttle service to Old Town, running maps, and Bootcamp in a Box. We also have a Starbucks on-site, as well as an awesome pool area, lounge, poolside restaurant, and clean, comfortable rooms.

Check out our rooms here, and look to see which of our online specials work for you.