The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]
35 events found.
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2 events,Mile 0 Fest 2026 is the premier boutique festival for Red Dirt and Americana music, bringing the heart of the Texas and Oklahoma music scenes to the tropical shores of Key West. Now in its ninth year, the festival is celebrated for its intimacy, high-caliber songwriting, and “music in paradise” atmosphere. Festival Dates: January 27 […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The 17th Annual Key West Food & Wine Festival in 2026 is a premier culinary event that transforms the island into a world-class tasting destination. This year, the festival features a unique geographical focus, celebrating the bounty of the Pacific Coast through its “Red, White & Pacific Blue” theme. Festival Dates & Theme Dates: January […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
2 events,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] The First Fridays on Fleming is the signature monthly art stroll for Old Town Key West, specifically highlighting the “boutique” galleries and studios along the 500 block of Fleming Street. It serves as the island’s version of a First Friday Art Walk, offering a sophisticated but relaxed alternative to the rowdier Duval Street scene. 2026 […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […] The Monroe County Sheriff’s Animal Farm Open House is one of the most unique and heartwarming community attractions in the Florida Keys. Located on the grounds of the Stock Island Detention Center, this “jailhouse zoo” serves as a sanctuary for over 150 abandoned, abused, or confiscated animals, ranging from traditional farm residents to exotic species. […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
2 events,The 20th Annual Florida Keys Seafood Festival in 2026 is a milestone celebration of the island’s rich commercial fishing heritage. Unlike many tourist events, this is a true “local” feast—the food is caught, cleaned, prepared, and served by Florida Keys fishermen and their families. Festival Dates: February 14 – February 15, 2026 The festival is […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
2 events,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] The Morada Way Art Walk is the premier cultural event of the Upper Keys, turning the heart of Islamorada into a lively, open-air gallery and street festival. Held in the Morada Way Arts & Cultural District (Mile Marker 81.5), this “Third Thursday” tradition brings together local artists, musicians, and culinary talent for an evening that […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
3 events,The Upper Keys Rotary Gigantic Nautical Market (affectionately known as the “Gigantic Nautical Flea Market”) is the largest outdoor nautical show of its kind in the Florida Keys. Held at the expansive Founders Park, this two-day event is a massive “boat show with a beach,” attracting over 20,000 visitors who come to hunt for bargains, […] The Old Island Days Art Festival (now officially renamed the Key West Art & Craft Festival) celebrates its 61st anniversary in 2026. This prestigious, juried outdoor show is a cornerstone of the island’s winter season, transforming the waterfront into a sprawling gallery for some of the country’s finest artists and craftspeople. Festival Dates: February 21 […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
5 events,The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […] The Monroe County Sheriff’s Animal Farm Open House is one of the most unique and heartwarming community attractions in the Florida Keys. Located on the grounds of the Stock Island Detention Center, this “jailhouse zoo” serves as a sanctuary for over 150 abandoned, abused, or confiscated animals, ranging from traditional farm residents to exotic species. […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
2 events,he Truman Waterfront Farmers Market (often referred to simply as the Key West Farmers Market) is a weekly staple of island life. Held at the scenic, breezy end of the island, it is a “pop-up island bazaar” that serves as both a grocery stop for locals and a scenic lunch or sunset destination for visitors. […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
1 event,The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |
2 events,The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […] The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […] |