The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
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Events in the Florida Keys for October, 2022
Year: Month:  
August 24 to October 02,  in Islamorada
Florida Keys History & Discovery Center presents: 'The Study of Water' Exhibition
The Florida Keys are an island oasis nestled in a sea of water. The Study of Water reveals four differing artistic expressions and intimate connections with water. Throughout the exhibition, each artist provides individual interpretations and personal associations with water. The works collectively reveal how water provides nourishment, sanctuary, and healing. Featured artists include South Florida and Florida Keys artists: Castro Humberto, Jul Jankowski, Derrick Crossland, and Lisa Lee Herman. Exhibit is open during business hours Tuesday-Sunday, 10am-5pm as part of museum admission through October 2, 2022. A gallery opening reception is to be held Aug. 24 from 5-7 pm. Admission is free and cash bar available.

September 06 to October 16,  in Key West
‘Kids Free Florida Keys’
Through Oct. 16, families can explore Florida Keys attractions, tours, watersports and other offerings with a value-added program that provides free admission or opportunities for children ages 12 and under. Download coupons for visits to nature-themed and historic attractions, restaurants and activities ranging from snorkel tours to aquarium explorations. The site features links to participating businesses and information about their offerings. Each child must be accompanied by at least one paying adult. Presented by the Key West Attractions Association.

September 29 to October 01,  in Key West
Comedy Key West Presents: Sally Brooks
Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Sally Brooks, a nationally touring stand-up comedian, writer and podcaster know for her personal stories of misadventure and fun-loving, smart-assed nature. She is the cohost of Dumb Love, a comedy podcast about the dumb things people will do for love. Show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.

September 30 to October 01,  in Islamorada
Conch Scramble Charity Golf Tournament
Floating greens, golf boats and biodegradable fish food balls highlight the annual “par-tee” on the water. Fans of golf and boating can expect to have a “hole” lot of fun honing their swings and raising money for charity one shot at a time. Teams of four and a designated boat driver “caddy” make stops at nine Islamorada waterfront venues and come ashore to tee off. Each player has two shots at the floating holes using biodegradable golf balls that dissolve into fish food after 90 hours in the water.

October 01,  in Key West
25th Annual Key West Paddle Classic
Watersports enthusiasts on paddleboards and other self-propelled watercraft can race around the continental United States’ southernmost island during the annual Key West Paddle Classic. Presented by Lazy Dog Adventures, the 12-mile challenge takes competitors past island landmarks such as the Southernmost Point marker, Fort Zachary Taylor Historic State Park and Mallory Square, site of Key West’s nightly sunset celebration.
Contact: Sue Cooper 305-304-4259
Email: [email protected]

October 01,  in Key West
Second Annual Key West Barbershop Music Fest
Enjoy the uniquely American style of close acapella harmony. The Miamians of South Florida, formed in 1948, won the international championship in 1965. Afterward, the Barbershop Harmony Society was formed and today there are chapters around the world, with men and women singing and competing. Performance begins at 7 p.m., at Key West United Methodist Church, 600 Eaton St. The Miamians barbershop chorus shows benefit local charities. Tickets are $30 at the door.
Email: [email protected]

October 02,  in Marathon
Fall Harvest Fun at Crane Point Hammock Museum & Nature Trail
Families of all ages are welcome to come and enjoy a petting zoo, hayrides, kids face painting, bubbles and more. From 4-7:30 p.m., inside Crane Point, 5550 Overseas Highway. Adult beverages and food will be available for purchase. Donation admission is $8 per adult, $5 kids, age 3 and under admitted free.

October 06 to October 08,  in Key West
Comedy Key West Presents: Billy Anderson
Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Billy Anderson. He can be heard on Audible’s “Sounds Like America” hosted by Jackie Kashian and seen on season 3 of the syndicated program “Laughs” on Fox television. Show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.

October 07 to October 09,  in Islamorada
Ladies Let’s Go Fishing! Keys Saltwater Weekend Seminar & Fishing Fever Inshore/Offshore Tournament
Female fishing fans can learn or polish angling skills during the award-winning weekend seminar. More than 8,000 female graduates have immersed themselves in the annual lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing.
Contact: Betty Bauman 954-475-9068
Email: [email protected]

October 10 to October 12,  in Islamorada
Islamorada All-Tackle Bonefish and Permit Championship
Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans in a competition that has taken place since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies for the three longest bonefish and three longest permit. The field is limited to 25 participants.
Email: [email protected]

October 13 to October 16,  in Key Largo
Reef Fest 2022: An Annual Celebration of Marine Conservation
REEF Fest includes diving, snorkeling, kayak eco-tours, ocean-themed seminars, and social events. Since 2015, REEF has hosted REEF Fest each fall in the Florida Keys. Divers, snorkelers, and ocean lovers attend REEF Fest to celebrate their love of marine life and learn about the latest in conservation. Weekend schedule is to include REEF Marine Conservation Programs, dive, snorkel and kayak trips, seminars with renowned ocean experts and more.
Email: [email protected]

October 13 to October 15,  in Key West
Legends of Music Row Music Festival
Book your tickets for this extraordinary three-night event, including an option for a VIP experience with an exclusive, up-close-and-personal concert setting featuring songwriting legends in country music. A musical experience like no other, Legends of Music Row is to be hosted by Country Music Hall of Fame songwriter Dean Dillon.

October 13 to October 27,  in Key West
“Bum Farto - The Musical”
Pasión Project presents “Bum Farto -The Musical,” a hilarious true crime musical that tells the tale of an infamous fire chief who tempted fate and federal agents who set him up in a 1975 Key West drug sting known as Operation Conch. The smokin’ hot show opens at the San Carlos Institute Theater in Old Town, Key West on Thursday, October 13 through October 27. Throw on your best bellbottoms, platforms, and polyester for a sizzling 70s Opening Night Gala featuring pre-show cocktails, hors d’oeuvres, and groovy tunes to benefit the Key West Firehouse Museum. Tickets start at $35 online.

October 15,  in Key West
Native Plant Sale at the Key West Tropical Forest & Botanical Garden
The plant nursery offers native trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month.  Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

October 19,  in Key West
Comedy Key West Presents: The Royal Roast of DJ Sanaris
It's hard to say something negative about the ever-positive, smiling DJ Sanaris, but this dais will find a way. Hosted by Roast Master Landon Bradbury along with other local comedians and notable Key West celebrities. A DJ Sanaris for King event. Complimentary nibbles provided by Little Whitehouse Subs & Layla's Gather & Nourish. Doors open at 7:00 p.m., show starts at 8:00 p.m. Comedy Key West is located at 218 Whitehead St.

October 20 to October 22,  in Key West
Comedy Key West Presents: Dean Napolitano
Comedian Dean Napolitano is a throwback to the great comedians of yesteryear with a modern twist that makes him one of the most prevalent comedians working today. A true storyteller with imaginative delivery that makes audiences feel as if they have been through each experience themselves.Doors open at 7:30 p.m., show starts at 8:30 p.m. Comedy Key West is located at 218 Whitehead St.

October 21 to October 30,  in Key West
Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2022 theme is ‘Cult Classics and Cartoon Chaos!' Check the website for the full schedule and more details.

October 21 to October 22,  in Key West
Bahama Village Goombay Festival
Held in Key West's historic Bahama Village neighborhood, the lively, family-friendly Goombay is known for its island-style food, arts and crafts, nonstop live entertainment and dancing in the streets. Visitors can experience sights, sounds and flavors recalling Key West's Bahamian heritage. FREE event, noon to midnight both days.

October 22,  in Key West
Smallest Parade in the Universe
Everyone’s favorite miniature parade returns! Artists compete for cash prizes and bragging rights with pint-sized floats to suit this year’s Fantasy Fest theme: Cult Classics and Cartoon Chaos! The fantastical entries are on view all month before being auctioned Oct 22 at 7 p.m., at The Studios of Key West, and 533 Eaton St., with proceeds to benefit MARC House.

October 23,  in Key West
Zombie Bike Ride
A pre-Halloween tradition for visiting and local families and groups, the ride typically draws several thousand men, women and children — and even a few pets. Garbed in ragged costumes and frightening face and body makeup, they pedal along the island city's Atlantic Ocean shore in a deliciously scary spectacle. The wacky event begins at 2 p.m. when Zombie Land opens, at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd. Live music, entertainment and face painting. Register for $5 per person.

October 24,  in Key West
Heroes and Villains 5k Run/Walk
Be super, be evil, be awesome and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40+) male and female winners. Register online. Race starts at 6 p.m. The race begins and ends at Southernmost Beach Café.
Contact: Beth Moyes 305-747-8563
Email: [email protected]

October 25 to October 28,  in Key West
Key West Burlesque presents: Burlesquers Stripfinity War
In a different dimension of the multiverse, the salacious stripping superhero's known as the Burlesquers must enlist the help of the Garters of the Galaxy to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque and celebrity out of town guests. Tickets and showtimes available online; doors open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.

October 26,  in Key West
Pet Masquerade
This year’s carousel of frisky pets and playful owners perform for fame, fortune and prizes onstage at Key West Amphitheater, at Truman Waterfront Park. Starts 6:30 p.m. Proceeds benefit the Lower Keys Friends of Animals; free to watch.

October 27,  in Key West
39th Annual Key West Headdress Ball
Talented headdress makers compete for first- through third-place prizes. The popular event returns to the Coffee Butler Amphitheater, Truman Waterfront Park. Doors open to the outdoor gala around 6:30 p.m., show starts 8 p.m. Sponsored by the Key West Business Guild. Tickets for purchase online.

October 28,  in Key West
Masquerade March
Costumed merrymakers parade through Old Town. Begins at Old Town Wine & Spirits, Truman Avenue at 5:30 pm; free to join the crowd as they parade through Old Town with music and noisemakers.

October 28 to October 29,  in Islamorada
Fall Backcountry Fly Championship Series
Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals 1 point. Awards are to be given to the grand champion, the anglers who catch the largest snook and redfish and the “King of the Backcountry” series grand champion, among others.

October 29,  in Key Largo
Underwater Pumpkin Carving Contest
Scuba divers can participate in a fun-filled buddy challenge to create the most unique Jack O'Lantern underwater during both dives of the afternoon charter! The contest will be held in the Florida Keys National Marine Sanctuary and the Amoray Diver crew will judge the entries. Dive purchase includes a two-tank dive trip, a cleaned pumpkin ready for carving, tanks and weights. Check in to Amoray Dive Center, mile marker 104.2, at 12:30 p.m. Bring your favorite carving utensils and creative ideas! Prizes awarded to the top three carved pumpkins.
Contact: 305-451-3595

October 29,  in Key West
Bud Light Fantasy Fest Parade
Lavishly decorated floats, costumed characters, bands and elaborately garbed marching groups are to make a splash on Key West's Duval Street. The glittering parade is the traditional highlight of the annual Fantasy Fest masking and costuming celebration. Parade steps off at 7 p.m. Floats, bands and other parade participants traditionally travel down Whitehead toward the Gulf of Mexico, turn onto Front Street and then proceed the mile down Duval to the Atlantic Ocean.

October 29,  in Key West
Key West Woman's Club Parade Viewing Dinner Party
Experience exceptional viewing of an extraordinary parade as it rolls down Duval Street. A costumed theme is “Betty Boop” and a three-course VIP exclusive catered dinner is to be served. Priority seats remain; make reservations early. Red carpet treatment is $275 per person. The Key West Woman’s Club, a volunteer service organization, is housed in a building that is one of the few privately owned mansions remaining on historic Duval Street. Proceeds are to benefit its continued restoration.
Contact: RSVP 305-294-2039
Email: [email protected]

October 30,  in Key West
Rams Head presents The Wallflowers
For the past 30 years, the Jakob Dylan-led act has stood as one of rock’s most dynamic and purposeful bands – a unit dedicated to and continually honing a sound that meshes timeless songwriting and storytelling with a hard-hitting and decidedly modern musical attack. Does open 7 p.m., show starts 8 p.m. at Key West Theater, 512 Eaton St.
Contact: Box Office 305-985-0433
Email: [email protected]

The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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