Key West Live Music & Concerts

Browse Hey Key West's current live music event grouping, with dates, venues, and details.

Zack Seemiller — October 19, 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 19, 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 19, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Igor And The Red Elvises 5:30, 9:00 & 11:00 — October 20, 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 It’s the return of "Your Favorite Band!", Siberian Surf-Rockers Igor and The Red Elvises, two days and nights of their unique blend of Russian folk music, 50’s rockabilly, surf, reggae, and whatever-else-makes-them-happy! (Browse group: Live Music)
T-Baum & The Tall Boys — October 20, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Harley Ray — October 20, 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 20, 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 21, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Andy Mauerman — October 21, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Igor And The Red Elvises 5:30, 9:00 & 11:00 — October 21, 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 It’s the return of "Your Favorite Band!", Siberian Surf-Rockers Igor and The Red Elvises, two days and nights of their unique blend of Russian folk music, 50’s rockabilly, surf, reggae, and whatever-else-makes-them-happy! (Browse group: Live Music)
Dan Harvey Duo — October 21, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Sharese — October 22, 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 22, 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 22, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
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)
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)
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)
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)
Zack Seemiller — October 26, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Heather Vidal — October 26, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Jimmy Parrish & The Waves — October 26, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Jimmy Parrish & The Waves — October 27, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Heather Vidal — October 27, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Harley Ray — October 27, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Waynard Scheller and Rainbow Full of Sound at 5:30, 8:30 & 10:30 — October 27, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 and 10:30-12:00. Waynard Schiller and Rainbow Full of Sound, one of the East Coast’s premiere Grateful Dead tribute bands, who have made re-creating precise sets from the Dead’s legendary appearances their mainstay, particularly the twenty-one memorable shows of Dead’s European tour in 1972 will appear at The Green Parrot (Browse group: Live Music)
Jimmy Parrish & The Waves — October 28, 2026 · 8:30 PM – 12:30 AM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Heather Vidal — October 28, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Andy Mauerman — October 28, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Waynard Scheller and Rainbow Full of Sound at 5:30, 8:30 & 10:30 — October 28, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Three 90-minute sets: 5:30-7:00, 8:30-10:00 and 10:30-12:00. Waynard Schiller and Rainbow Full of Sound, one of the East Coast’s premiere Grateful Dead tribute bands, who have made re-creating precise sets from the Dead’s legendary appearances their mainstay, particularly the twenty-one memorable shows of Dead’s European tour in 1972 will appear at The Green Parrot (Browse group: Live Music)
Sharese — October 29, 2026 · 11:30 AM – 3:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Heather Vidal — October 29, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Jimmy Parrish & The Waves — October 29, 2026 · 8:30 PM – 8:30 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)
Heather Vidal — October 30, 2026 · 4:00 PM – 8:00 PM · Hog's Breath Saloon: Live music at Hog's Breath Saloon. (Browse group: Live Music)