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Your Weekend Guide to Key West
August 21 – August 23, 2026 · 22 events
This weekend in Key West, Florida brings 22 live events across the city — from music. 1 events are explicitly listed as free. Here's what's on.
Key West may be the most reliably live-entertainment-dense town in America — Duval Street alone offers more stages per block than most cities' entire downtowns. Sloppy Joe's carries its Hemingway-era legend with bands playing day and night, while the Green Parrot, a locals' institution since 1890, books some of the best roots and funk acts to make the drive down the Overseas Highway. Every evening, Mallory Square's sunset celebration turns street performance into civic ritual. Fantasy Fest each October is the island's gloriously unhinged answer to Mardi Gras, and Hemingway Days each July celebrates the island's most famous resident with readings, contests, and general mischief.
Sunday (6)Music (17)
Events in Key West This Sunday
6 events are listed for Sunday, including Tim Bradach at Irish Kevin's, Aaron Blumer at Hog's Breath Saloon, James Kelly at Irish Kevin's, Matt Zavala Jonny Gray at Hog's Breath Saloon. Events that start earlier in the weekend may still be running Sunday; open an event for its current schedule.
Thursday, August 20
Friday, August 21
Saturday, August 22
Sunday, August 23
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Frequently Asked Questions
- What's happening in Key West this weekend?
- There are 22 events happening in Key West this weekend (August 21 – August 23, 2026), including Tim Bradach at Irish Kevin's, Jeff Harris at Irish Kevin's, Harley Ray at Hog's Breath Saloon, James Kelly at Irish Kevin's. Browse the full lineup on VenuNite.
- Are there free things to do in Key West this weekend?
- Yes — 1 events in Key West this weekend are explicitly listed as free. Confirm current entry details on the event page or organizer source.
- What events are happening in Key West this Sunday?
- 6 listed events are happening in Key West this Sunday, including Tim Bradach at Irish Kevin's, Aaron Blumer at Hog's Breath Saloon, James Kelly at Irish Kevin's, Matt Zavala Jonny Gray at Hog's Breath Saloon.
- Where can I find things to do in Key West, Florida?
- VenuNite aggregates live events from venues across Key West. Browse by date, venue, or event type to find what's happening near you.
