October 2026 Key West Events & Festivals

Plan your Key West trip with this calendar of October 2026 events, festivals, concerts, and things to do.

TUTU SALSA SESSIONS — October 19, 2026 · Southernmost Beach Resort: Tuesday, October 20, 2026. Celebrate one of Fantasy Fest’s most colorful traditions during Tutu Tuesday at Southernmost Beach Café, where beachfront drinks give way to an evening of salsa dancing, festive attire, (Browse group: Festivals)
The Greatest Hits Pool Party — October 19, 2026 · Winslow's Bungalows: Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows, part of the 2026 Fantasy Fest celebration in Key West. (Browse group: Festivals)
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)
Party in My Pants: A Sexy Ass Cabaret (10/19) — October 19, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
The Beatle Band at 5:30, 9:00 & 11:00 *Offical Fantasy Fest Event — October 19, 2026 · 5:30 PM – 11:59 PM · Green Parrot Bar: Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, re-create a Fab Four Show with "THE BEATLE BAND, All You Need is Love" with shows at 5:30, 9:00 and 11:00pm. Their past Beatle Tribute Shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang along to a set-list pulled from decades of Lennon-McCartney hits. Photo Credit: Bill Klipp (Browse group: Festivals)
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)
Key West Farmers Market — October 20, 2026 · 1:00pm - 6:00pm · Truman Waterfront: A weekly market featuring local produce, crafts, and goods from local vendors. (Browse group: Food & Drink)
Party in My Pants: A Sexy Ass Cabaret (10/20) — October 20, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
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)
Fantasy Fest — October 21, 2026 · Duval Street: A 10-day festival featuring themed parties, parades, and costume contests, celebrating the spirit of Key West. (Browse group: Festivals)
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)
Party in My Pants: A Sexy Ass Cabaret (10/21) — October 21, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
Goombay Festival — October 22, 2026 · Bahama Village: A vibrant celebration of Bahamian culture with music, food, and arts in the heart of Bahama Village. (Browse group: Festivals)
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)
Party in My Pants: A Sexy Ass Cabaret (10/22) — October 22, 2026 · 8:00 PM (Doors 7:30 PM) · Key West Theater (Browse group: Arts & Culture)
FUNK IT UP Party with Trae Pierce & The T-Stones at 5:30, 9:00 & 11:00 *Official Fantasy Fest Event — October 22, 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 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: Festivals)
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)
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)