Calendar of Events
October 2022: Florida Keys Events
- Sponsored Event
- Mar 29, 2025 - Mar 30, 2025 Key West
- NAS Key West Southernmost Air Spectacular
- Website Boca Chica Field, Key West
- Naval Air Station Key West FL 33040
- NAS Key West E-mail
- View video
- The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
- Buy tickets!
- Sponsored Event
- Jan 18, 2025 - Jan 19, 2025 Key West
- Key West Half Marathon & Runfest
- Website Key West Historical Seaport
- 231 Margaret Street Key West FL 33040
- 305-240-0727 E-mail
- View video
- The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
- Buy tickets! Call now!
- Sponsored Event
- Nov 18, 2024 - Dec 30, 2024 Key West
- Waterfront Winter Wonderland
- Website
- 21 Quay Rd Key West FL 33040
- Liz Love E-mail
- Enjoy Visits with Santa, live music performances, and festive celebrations throughout the season! Home to Key Wests only ice rink, we will also have thrilling carnival rides and fun for the whole family at Waterfront Winter Wonderland!
- Buy tickets!
- Mar 31, 2022 - Dec 11, 2022 Key West Arts & Culture
- Key West Bicentennial Exhibit at The Custom House Museum
- Website
- Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.
- Aug 24, 2022 - Oct 2, 2022 Islamorada Arts & Culture
- Florida Keys History & Discovery Center presents: 'The Study of Water' Exhibition
- Website
- 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.
- Sep 6, 2022 - Oct 16, 2022 Key West
- ‘Kids Free Florida Keys’
- Website
- 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.
- Sep 29, 2022 - Oct 1, 2022 Key West Arts & Culture
- Comedy Key West Presents: Sally Brooks
- Website
- 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.
- Oct 1, 2022 Key West Environmental
- 25th Annual Key West Paddle Classic
- Sue Cooper 305-304-4259 E-mail Website
- 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.
- Oct 1, 2022 Key West Arts & Culture
- 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.
- Oct 2, 2022 Marathon Arts & Culture
- Fall Harvest Fun at Crane Point Hammock Museum & Nature Trail
- Website
- 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.
- Oct 6, 2022 - Oct 8, 2022 Key West Arts & Culture
- Comedy Key West Presents: Billy Anderson
- Website
- 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.
- Oct 6, 2022 - Oct 27, 2022 Key West Arts & Culture
- Sea Level Stories: Jane Lawton Baldridge Art Exhibition
- Website
- Baldridge displays large abstract seascape paintings to bring awareness to the mounting threats of flooding and sea level rise with the goal of inspiring our community to unify in solving these issues. On view through Oct. 27 at The Studios of Key West, 533 Eaton St.
- Oct 9, 2022 - Nov 2, 2022 Islamorada Arts & Culture
- Dia de los Muertos Ancestral Celebration
- Website
- The annual Dia de los Muertos Ancestral Celebration at the Florida Keys History & Discovery Center includes traditional altar displays and memory tables on view daily, as well as special events. The main celebration takes place Nov. 2 with a sugar skull workshop (2-5 p.m., $5 per person, advance registration required); and the free annual ancestral procession at 5 p.m. from the center to Florida Keys Brewing Co. The procession will be led by the Ameyal Mexican Folklore Ensemble dressed in their exquisite themed attire. Performances at the brewery will include multi-generational performers sharing many genres of Afro-Mexican folk dance and music.
- Oct 12, 2022 Islamorada Arts & Culture
- Smuggling in the Florida Keys: Part 1
- Website
- Part I of the Florida Keys History & Discovery Center lecture series, “Smuggling in the Florida Keys,” features Richard Russell and Ricou Deshaw sharing details of their individual adventures and being on opposite sides of smuggling in the Florida Keys. Doors open at 5 p.m. to explore the museum exhibits with light appetizers and a cash bar. Presentation 6-7:30 p.m. Advance registration required, $10.
- Oct 13, 2022 - Oct 27, 2022 Key West Arts & Culture
- “Bum Farto - The Musical”
- Website
- 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.
- Oct 17, 2022 - Oct 21, 2022 The Florida Keys
- "Be Like Mike" in the Florida Keys
- Website
- To honor the memory of Mike "Mangrove Mike" Forster, a favorite Middle Keys businessman, public official and community supporter, the United Way of Collier and the Keys is encouraging visitors and residents to #BeLikeMike with acts of community support and kindness the week of Oct. 17-21. Take a few moments to support marine conservation, help feed children, or care for animals and each other. Check online for ideas and post about your efforts on social media with #BeLikeMike.
- Oct 19, 2022 - Nov 12, 2022 Key West Arts & Culture
- Jimmy Buffett's Escape to Margaritaville
- Website
- Key West's Waterfront Playhouse on Mallory Square opens its 84th season with Jimmy Buffett’s Escape to Margaritaville. A madcap love story, erupting volcano, tap dancing zombies and Buffett classics like Cheeseburger in Paradise, Margaritaville, It’s Five O’Clock Somewhere and Son of a Son of a Sailor will fill the air on Mallory Square through November 12. The show features a margarita bar onstage during intermission. Tickets available online or by calling 305-294-5015.
- Oct 19, 2022 Key West Arts & Culture
- Comedy Key West Presents: The Royal Roast of DJ Sanaris
- Website
- 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.
- Oct 20, 2022 - Oct 22, 2022 Key West Arts & Culture
- Comedy Key West Presents: Dean Napolitano
- Website
- 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.
- Oct 21, 2022 - Oct 30, 2022 Key West LGBTQ
- Key West Fantasy Fest
- Website
- 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.
- Oct 21, 2022 - Oct 22, 2022 Key West
- Bahama Village Goombay Festival
- Website
- 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.
- Oct 22, 2022 Key West
- Smallest Parade in the Universe
- Website
- 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 at The Studios of Key West, 533 Eaton St., before being auctioned off on Oct. 22, with proceeds to benefit MARC House.
- Oct 22, 2022 Marathon
- Witches in the Hammock
- Website
- Come in costume and enjoy the annual Witches in the Hammock experience at Crane Point Museum & Nature Trail. Take a torch walk along the Crane Point Hammock nature trail to some place haunted. Visit Casper the Friendly Ghost and play games with pirates. Adults $10, kids $5. Adult beverages will be available for purchase. 6:30 to 9 p.m. Oct. 20 and 21. 5550 Overseas Hwy, Marathon.
- Oct 23, 2022 Key West
- Zombie Bike Ride
- Website
- 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.
- Oct 24, 2022 Key West
- Under the Sea Party for Reef Relief
- Website
- Come as your favorite sea creature to the Under the Sea Party from 12-6 p.m. Oct. 24. Enjoy great music, the costume contest, raffles, cash prizes, drink specials and more. Proceeds will benefit Reef Relief's efforts to promote marine conservation through education and outreach. Presented by Reef Relief and Dante's Key West Pool Bar, 951 Caroline St., Key West. Must be 21 or older to participate. Call 305-294-3100 or email reefrelief@gmail.com for more information.
- Oct 25, 2022 Key West Arts & Culture
- Rock the Reef
- Website
- Mote Marine Laboratory partners with Ocean Key Resort & Spa, a Noble House Resort, for the inaugural 'Rock the Reef' costume contest and concert featuring Suenalo at Sunset Pier, 0 Duval St., on Tuesday, Oct. 25th. This free, family-friendly event during Fantasy Fest kicks off at 5 p.m. featuring costume contests judged by local celebrities with categories for kids (12 and under), fur-babies, and adults. The kids division will be judged at 5:30 p.m., fur-babies (on lease/in hand) at 5:45 p.m., and adults at 6 p.m. There will be educational activities highlighting Florida's Coral Reef and Mote's coral research & restoration efforts throughout the Florida Keys. At 7 p.m., Suenalo, the Miami-based 8-piece Afro-Latin-funk-jam band, will take the Sunset Pier center stage. Dance the night away with the hottest band from Miami, as Suenalo mixes afro sounds and funk with a dose of hip-hop, reggae, rock and jazz. This event is free but donations are encouraged; proceeds will benefit Mote's science-based coral reef restoration efforts.
- Oct 25, 2022 - Dec 31, 2022 Islamorada Arts & Culture
- History of Diving Museum: Sponge Hunters
- Website
- Sponge Hunters: Key West Hookers, Bahamian Free Divers, and the Hard Hat Divers of Tarpon Springs will be on display May 19 through December 31, 2022. Learn about the sea sponge and its uses, from the long history of fishers to modern fisheries, current restoration efforts and the various dive methods used in seeking out this treasured aquatic animal. Mile marker 83 bayside, Islamorada. 10 a.m. - 5 p.m. daily except Thanksgiving, Christmas Day, and New Year’s Day.
- Oct 25, 2022 - Oct 28, 2022 Key West
- Key West Burlesque presents: Burlesquers Stripfinity War
- Website
- 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.
- Oct 26, 2022 Islamorada Arts & Culture
- Smuggling in the Florida Keys: Part II
- Website
- Part II of the Florida Keys History & Discovery Center lecture series, “Smuggling in the Florida Keys,” features law enforcement officials as they share stories of Smuggling in the Florida Keys and run-ins with those involved. Panel includes Sheriff Rick Ramsay, MSO Captain Don Hiller, Ret. former Marine Patrol and FWC Mike Long, Capt. David Dipre, FWC and more. Doors open at 5 p.m. to explore the museum exhibits with light appetizers and a cash bar. Presentation 6-7:30 p.m. Advance registration required, $10.
- Oct 26, 2022 Key West
- Pet Masquerade
- Website
- 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.
- Oct 27, 2022 - Nov 4, 2022 Key Largo Arts & Culture
- The Keys Players: Little Shop of Horrors
- Website
- An incredible cast and amazing voices from The Keys Players brings to life the fabulous show Little Shop of Horrors at the Murray E. Nelson Government & Cultural Center in Key Largo. Adult tickets available online and at the door for $23; high school or younger tickets $10 at the door only with proof of age.
- Oct 27, 2022 - Nov 12, 2022 The Florida Keys Arts & Culture
- Rocky Horror Show
- Website
- Rocky Horror fans, don't miss the opportunity to see the cult classic stage musical, The Rocky Horror Show, at Marathon Community Theater. Sassy audience participation is expected including cascading toilet paper and an array of other audience participation props. This deliberately kitschy rock 'n' roll sci-fi gothic musical is more fun than ever. Let's Do the Time Warp Again! Tickets available online. 5101 Overseas Highway, Marathon.
- Oct 27, 2022 Islamorada
- Treasure Treat Night at History of Diving Museum
- Website
- Looking for some ghoulishly good fun this month? Join the History of Diving Museum on Thursday, Oct. 27th for Treasure Treat Night! This two-hour event will include trick-or-treating inside the museum, kid's activities, a costume contest with prizes, raffles, and a spooky exhibit experience with costumed staff. Mile marker 83 bayside, Islamorada. Admission is a $5 suggested donation.
- Oct 28, 2022 Marathon
- Get down to Havana Jack's in Key Colony Beach from 7 to 10 p.m. Friday, Oct. 28 for the Boo Bash and costume contest. The event supports Presents in Paradise, which raises money to help out local kids for Christmas. Wear your best costume and compete for great prizes and enjoy live music. Glunz Beach Resort, 401 E. Ocean Dr.
- Oct 28, 2022 Key West
- Fantasy Fest "Fantasy Market" at Truman Waterfront Park
- Website
- The Fantasy Fest Street Fair has been moved to the Truman Waterfront Park. The new “Fantasy Market” takes place Friday, Oct. 28 from 10 a.m. to 5 p.m., offering shopping, costumes and accessories, fun entertainment, and food and beverage. Vendors, makers, artists, crafters, photographers, jewelry, apparel, costumers, toys, non-profits, sponsors, culinary, food trucks and more will be set up in the grass near the splash park at the picturesque Truman Waterfront Park overlooking the Atlantic Ocean. Family and pet friendly. 100 Southard Street, KeyWest.
- Oct 28, 2022 Islamorada
- Theater of the Sea Halloween Show
- Website
- Theater of the Sea's first annual Halloween Show takes place Friday, Oct. 28 at the park, located at mile marker 84 oceanside in Islamorada. Buy tickets online or at the door - $10 per person, kids age 3 and under get in free. Doors open at 5:30 p.m. for the special Pirates of the Florida Keys dolphin show, presented by Theater of the Sea's Waterwork Team.
- Oct 28, 2022 - Oct 29, 2022 Islamorada Fishing
- Fall Backcountry Fly Championship Series
- Website
- 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.
- Oct 28, 2022 Key West
- Masquerade March
- Website
- 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.
- Oct 29, 2022 Key West
- Bud Light Fantasy Fest Parade
- Website
- 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.
- Oct 29, 2022 Key West
- Key West Woman's Club Parade Viewing Dinner Party
- RSVP 305-294-2039 E-mail
- 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.
- Oct 29, 2022 Key Largo
- Underwater Pumpkin Carving Contest
- 305-451-3595 Website
- 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.
- Oct 29, 2022 Key West
- Screaming Green Halloween at Key West Tropical Forest & Botanical Garden
- Website
- The annual 'SCREAMIN’ GREEN HALLOWEEN' at the Historic Key West Tropical Forest & Botanical Garden will be held on Saturday, October 29, 2022. The Gates are open from 10am – 2pm for children to have a fun and safe ‘Trick or Treat’. Tricks, treats, games, and recycle ideas will be set up throughout the garden so kids can be in costume while exploring the Garden and participating in tricks and the hunt for treats! There will be two costume contests. Prize will be awarded for ages 5 and under at 12:15 & ages 6 – older at 1:15. Entrance Fee: $5 per child or $10 per family. The Garden is located at 5210 College Road on Stock Island. For more information call 305-296-1504.
- Oct 29, 2022 Key Largo
- Halloween at Pennekamp
- Website
- Join park rangers, staff and community members from 4:30-7:30 p.m. Saturday for a family-friendly Halloween celebration at John Pennekamp Coral Reef State Park. Activities include Trunk or Treat, the Not So Scary Aquarium, Halloween crafts, photos with a mermaid and presentations in the auditorium: 6 p.m. REEF presents Creepy Critters, and 7 p.m., a presentation from Captain Coral. Prizes will be awarded for best costume and best trunk at the Trunk or Treat. Park admission is $4 per car plus $.50 per person over 5 years old. Donations can be made online and at the event to the Florida Park Service Ranger Association to assist state park staff and volunteers affected by Hurricane Ian.
- Oct 30, 2022 Key West Arts & Culture
- Rams Head presents The Wallflowers
- Box Office 305-985-0433 E-mail Website
- 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.