The first time we visited Key West in October, we were excited to celebrate… Halloween. Little did we know that’s not the event to celebrate in Key West, because October is all about Fantasy Fest. Well, and other things too. What are the best things to do in Key West in October?
Of course, we have to talk about the weather. Everyone hopes their Key West vacation is filled with sunny and warm days, right? Well, we know that isn’t always the case. October’s average temperature is in the low to mid 80’s. Humidity, well you know that’s still going to be a factor.
At night, expect temperatures to drop to the upper 70’s. Still very nice weather. October can be rainy. About 12 days this month will see rain with the average rainfall over 5 inches. But don’t fret, there are lots of things to do on rainy days in Key West.
Don’t worry about the water temperature either. You can spend time on and in the water for sure!
The best water activities in Key West
October is still considered hurricane season, so, I would recommend flexibility with your plans. We just never know if a hurricane or tropical storm may make an appearance.
Plans, Planes, and Place to Stay
If you love the weird and funky side of Key West, October is the best time to visit. The first part of the month will be slow, but towards the end of the month … well hold on! It’s Fantasy Fest time. During the festivities, there are parades, street fairs, and so much fun. Want to avoid a lot of the crowds? Go snorkeling around the coral reef, or head out on a sunset cruise.
What Not to Miss While in Key West
Planning to fly into Key West International Airport? No need to rent a car, you can walk or take the Duval Loop around the island.
Driving down the Keys? Plan to enjoy the drive, take a few days. Stay in Key Largo, Islamorada, or even Marathon.
Ultimate Road Trip from Miami to Key West
Hotel rooms, well honestly, they will be priced by demand. The period during Fantasy Fest can be pricy. So be aware. But, early in the month, still ok pricing and it’s a great time to explore the island. Much like the summer months, it can be considered “off season”.
Activities During October
25th Annual Key West Paddle Classic – October 1
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, the site of Key West’s nightly sunset celebration.
Second Annual Key West Barbershop Music Fest – October 1
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.
Comedy Key West Presents: Billy Anderson – October 6 – 8, 2022
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.
Reef Fest 2022: An Annual Celebration of Marine Conservation – October 13 – 16, 2022
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.
Legends of Music Row Music Festival – October 13-15, 2022
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.
“Bum Farto – The Musical” – October 13-27, 2022
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.
Comedy Key West Presents: The Royal Roast of DJ Sanaris – October 19
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.
Comedy Key West Presents: Dean Napolitano – October 20-22, 2022
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.
Bahama Village Goombay Festival – October 21`-22, 2022
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.
Key West Fantasy Fest – October 21-30, 2022
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.
Smallest Parade in the Universe – October 22
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.
Zombie Bike Ride – October 23
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.
Heroes and Villians 5k Run/Walk – October 24
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 be 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.
Key West Burlesque Presents: Burlesquers Stripfinity War – October 25-28, 2022
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.
Pet Masquerade – October 26
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.
39th Annual Key West Headdress Ball – October 27
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.
Masquerade March – October 28
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.
Bud Light Fantasy Fest Parade – October 29
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.
Key West Woman’s Club Parade Viewing Dinner Pary
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.
Underwater Pumpkin Carving Contest – October 29
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
Rams head Presents the Wallflowers – October 30
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.
Key West Bicentennial Exhibit at The Custom House Museum – until December 11, 2002
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.
Florida Keys History & Discovery Center presents: “The Study of Water” Exhibition – Until October 2, 2022
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.
Kids Free Florida Keys – Until October 16, 2022
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.