Key West Events This Weekend
Find festivals, concerts, nightlife, and things to do in Key West this weekend.
- LuffKid & Friendz Soundcheck Set — October 23, 2026 · 5:30 PM – 7:00 PM · Green Parrot Bar: One 90-minute set: 5:30-7:00. (Browse group: Nightlife)
- Elle Haley — October 23, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- Dan Harvey Duo — October 23, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- Party in My Pants: A Sexy Ass Cabaret (10/23) — October 23, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
- T-Baum & The Tall Boys — October 23, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- Trae Pierce & The T-Stones at 7:00, 9:00 & 11:00 — October 23, 2026 · 7:00 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 7:00-8:30, 9:00-10:30, and 11:00-12:30 set times could change Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Live Music)
- Trae Pierce & The T-Stones at 5:30, 9:00 & 11:00 — October 24, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 9:00-10:30, and 11:00-12:30 (times may change). Four-time Grammy Award winning funk master Trae Pierce and his band the T-Stones return to our stage for a funky good weekend. Trae and his band members consider the Parrot stage as merely their launching pad as they swarm into the crowd with their infectious beats and can't-stay-in-your-seat dance-moves. Pierce gets audiences fired up with his funky talk box versions of 2Pac’s “California Love,” Phil Collin’s “In the Air Tonight,” and “24K Magic” by Bruno Mars while The T-Stones’ lead vocalist Pierce’s son, Ray Pierce, adds a hip-hop flavor to the music. Speaking of flavor, fun fact: Ray has his own famous connections having been Flava Flav’s roommate in California for several years... (Browse group: Live Music)
- Harley Ray — October 24, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- T-Baum & The Tall Boys — October 24, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- Dan Harvey Duo — October 24, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- T-Baum & The Tall Boys — October 25, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- Sam Carlson Sound at 1:00 and 3:00 — October 25, 2026 · 1:00 PM – 4:30 PM · Green Parrot Bar: Two sets: 1:00-2:30 and 3:00-4:30. Sam Carlson leads his Bluegrass/Americana Quartet onto the The Parrot stage (Browse group: Arts & Culture)
- Dan Harvey Duo — October 25, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
- The Happy Dog at 5:30 & 7:30 — October 25, 2026 · 5:30 PM – 9:30 PM · Green Parrot Bar: Two sets: 5:30-7:00 and 7:30-9:30 (Browse group: Nightlife)
- Aaron Blumer — October 25, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)