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?
Weather
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. It’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 Places 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
Tuesday Evening GLOW Hours at Hugh’s Rooftop – March 13 – October 31, 2023
The Studios of Key West’s Hugh’s Rooftop offers the best views in town and an ideal spot to catch the sunset and a drink on Tuesday evenings from 6 to 8 p.m. through Oct. 31. Stay tuned for new hours beginning Nov. 7th after the time change when sunset will be earlier. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
Key West & Historical Society: Out of the Box – The Art of the Cigar Label – April 28 – October 22, 2023
The Key West Art & Historical Society presents “Out of the Box: The Art of the Cigar Label.” The exhibition offers a compelling sampling and interpretation of 19th and early 20th century inner and outer cigar labels, showcasing more than 40 lithographs related to the Key West and Cuba cigar manufacturers. Included with museum general admission. Custom House Museum, 281 Front Street, 10 a.m. to 5 p.m. daily.
Fort East Martello: Family Museum Day with Paper Kite-Making – October 1
Families of all ages are invited to explore Fort East Martello for free from 11 am. to 2 p.m. There will be a guided art program in making paper kites inspired by the late Cuban American folk artist Mario Sanchez. The program is free and registration is not required. The Fort is located at 3501 S. Roosevelt Blvd.
Fall Harvest at Crane Point Hammock – Marathon – October 1
Celebrate Fall at Crane Point Hammock and Nature Trail Sunday afternoon from 4 to 7:30 p.m. with games, hayrides, a puppet show and fall treats. Adult beverages are to be available for purchase. $10 adults, $5 kids, age 3 and under free. 5550 Overseas Highway bayside.
Crane Point Hammock: Sip & Sleuth – Marathon – October 5
Follow the clues to solve a crime and win prizes at Sip & Sleuth, a fun, interactive evening with Keys Mystery Theatre. $35 tickets available at Crane Point Gift Shop. The fun starts at 7 p.m. at the park, 5550 Overseas Highway bayside.
Marathon Community Theatre: Richard O’Brien’s Rocky Horror Show – October 5 – 21, 2023
Let’s do the Time Warp again! The cult classic interactive stage musical plays Thursday, Friday and Saturday nights through Oct. 21 with showtimes at 8 p.m.; along with one Sunday matinee on Oct. 15 at 3 p.m. This is an 18+ only show — IDs will be required at the door. Audience participation scripts, props, feather boas and other costumes are to be available for attendees. Tickets $33. Mile marker 49.5 oceanside.
Haunted Hosptial – October 6 – 8, 2023
Get ready for a night of spine-tingling chills and thrills at the Lower Keys Rotary’s Haunted Hospital & Hayride. Explore the eerie corridors of the abandoned hospital where ghosts of the past roam and creepy surprises wait behind every corner. The frightful fun starts at sunset Friday, Saturday and Sunday nights at Big Pine Community Park. 31009 Atlantis Blvd. Tickets $5 to $7.
Dogtoberfest – October 7
Bring your pup and your peeps to chill at Islamorada Brewery & Distillery for this annual celebration of fall, German lager, and most importantly, DOGS! Compete in the doggy costume contest at 1 p.m. and silly “Top Dog” competition for dogs and their humans at 3 p.m. Enjoy seasonal food & drinks for you and your furry friend throughout the day. Free event for all ages and all friendly dogs! The brewery garden is open from 11 a.m. to 8 p.m. MM 82 oceanside.
Islamorada Oktoberfest – October 8
Florida Keys Brewing Company brings Germany to Islamorada with a fun day for the whole family. Enjoy traditional German food, Oktoberfest decorations, face painting, a traditional 5-piece Oompah band and more from 2 to 6 p.m. in the beer garden at 81611 Old Highway.
Sheriff’s Animal Farm Open House – October 8
Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff’s Office Headquarters complex. The family-friendly Sheriff’s Animal Farm is open 1 – 3 p.m the second and fourth Sundays of the month.
Marathon Community Theatre: Monthly Fishing Seminar – Stone Crabs – October 9
This month’s fishing seminar presented by The Tackle Box is about stone crabs. Captain Chris still will talk about all there is to know about this local delicacy. The event includes door prizes and a 50/50 raffle. Monthly seminars are held at 6 p.m. at Marathon Community Theatre, mile marker 49.5 oceanside.
24 North Hotel: Paint & Sip Night with Artist Lance Berry – October 10
Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you’ll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.
Havana Jack’s: Oktoberfest – Marathon – October 13 – 15, 2023
Celebrate Oktoberfest with authentic German food, live music, beer boots and more at Havana Jack’s Oceanside in Key Colony Beach from 11 a.m. to 10 p.m. Friday, Saturday and Sunday. Come dressed in German garb and get one free beer. 401 E. Ocean Dr., Key Colony Beach.
Stock Island Cleanup & Community Day – October 14
Everyone is welcome to enjoy music, food, crafts, a silent auction and booths showcasing environmentally-minded organizations in the Coastlove Education Village at Bernstein Park, 6751 5th St., Stock Island from 10 a.m. to 2 p.m. Group cleanup teams are invited to register in advance to spend the morning cleaning up locations around Stock Island, but everyone can enjoy the celebration in the park.
Hispanic Heritage Month Celebration – Islamorada – October 14
Community Arts & Culture presents Cortadito, Miami’s version of the famed Buena Vista Social Club, along with DJ Le Spam, for an evening of live and selected music in the Beer Garden at Florida Keys Brewing Co., located in the Morada Way Arts & Cultural District, mile marker 81.6 oceanside. All ages are welcome. No cover. The music begins at 6 p.m.
Matercumbe Historical Trust Preservation: What the Heck is Archaeology? – October 17
All are welcome for this free presentation that is a quick and dirty intro to archaeology in South Florida and especially the Keys. Learn how people have been using the landscape of the Keys over the centuries. Malachi Fenn with Public Archaeology Network will discuss the ancient animals that roamed the islands and what tools and food people used in the distant past. 6 p.m. at Islamorada Public Library, mile marker 81.8 bayside.
Waterfront Playhouse: The Rocky Horror Show – October 18 – 27, 2023
Opening October 18 and Playing for 10 performances only will be a revival of Richard O’Brien’s The Rocky Horror Show. This wacky, tacky musical comedy traditionally plays to standing room only houses at the Waterfront Playhouse. Doors at 7 p.m., show at 8 p.m. 407 Wall St. at Mallory Square
History of Diving Museum: Immerse Yourself – Underwater Adventure with Ian Koblick – Islamorada – October 18
This free in-person Immerse Yourself presentation features famed Keys diving legend Ian Koblick. One of America’s first aquanauts, Ian is a pioneer in saturation diving and has designed underwater habitats. Join Ian as he speaks on his adventures in diving before there were rules, notable people he has been diving with, and his connections to sea and space. 7 p.m. at History of Diving Museum, mile marker 82.9 bayside.
Key West Theater: The Wailers – October 19
The Wailers perform one night only on Thursday, Oct. 19. Doors open at 7; show at 8 p.m. Tickets $53 to $73. 512 Eaton St.
Key West Art & Historical Society: Happy Hour with the Historian- October 19
This month’s Happy Hour with the Historian talk focuses on Key West Cuban-American folk artist Mario Sanchez. This talk highlights Sanchez’s sketches done on brown paper bags, a process he used to guide the layout of his famed bas-relief woodcarvings. His woodcarvings tell a story of Old Key West, melding art and history in a single scene. More than 70 sketches were recently donated by David Wolkowsky at the time of his death and will form the basis of this talk. $15 ticket includes one glass of wine, beer or soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead St.
Morada Way Third Thursday Art Walk – Islamorada – October 19
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
Reef Fest 2023: An Annual Celebration of Marine Conservation – Key Largo – October 19
Ocean lovers attend REEF Fest each fall to celebrate their love of marine life and learn about the latest in conservation. Hosted by the REEF Environmental Education Foundation, the schedule is to include dive, snorkel and kayak trips, seminars with renowned ocean experts, social gatherings and more.
Fantasy Fest: Fun & “Furryous” Coronation – October 20
Kick off Fantasy Fest at the Fun & “Furryous” Royal Coronation event to see who becomes the King and Queen of Fantasy Fest 2023! The King and Queen are each selected based on the most money raised to benefit the furry friends-in-need at Florida Keys SPCA. This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves. Each $100-per person ticket includes reserved seating, a 3-course plated dinner and two votes for the candidates of your choice. Reserved ticket sales close Oct. 15. General admission entry is FREE with open lawn space for self-seating. Cash bar for all. 6 p.m. doors, 7 p.m. show at Coffee Butler Amphitheater, 21 Quay Rd.
Fantasy Fest: Goombay Festival – October 20 – 21, 2023
This exuberant street party is the official kick-off for the annual Fantasy Fest costuming extravaganza with the action taking place noon to midnight both days. Find the main entertainment stage Key West’s Bahama Village neighborhood at the corner of Petronia and Fort streets. Popular musicians offer nonstop tunes in genres ranging from gospel to calypso and vendors offer multicultural taste treats. Other festival highlights include Friday night’s opening ceremonies and Saturday night’s Junkanoo Gawds Parade of costumed marchers and dancers, beginning at 6 p.m. and traveling through Key West’s historic downtown.
Key West Fantasy Fest – October 20 – 29, 2023
“Uniforms & Unicorns—200 Years of Sailing into Fantasy” is the official theme for Fantasy Fest 2023–Key West’s annual multi-day costuming extravaganza in Paradise. From October 20-29, revelers can explore an array of exciting events, including the world-famous Bud Light Fantasy Fest parade, the all-hands-on-deck Captain Morgan Masquerade March (aka “Locals Parade”), the exuberant Goombay Festival in the streets, Royal Coronation of the 2023 Fantasy Fest King, Queen, and royal court, plus concerts, theater productions, a “Heroes and Villains” 5K run/walk, the enchanting Key West Pet Masquerade, the 40th annual Headdress Ball pageant, and more.
Fantasy Fest: Barbie’s Pink Pool Party – October 20
Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort with DJ Tommy Tangie for a fun pool party that will also make you feel good! Along with great music, there is to be a Barbie or Ken costume contest, Barbie pink drink and food specials, and more – all to benefit Making Strides Against Breast Cancer in the Florida Keys. Tickets $10. The fun starts at 4 p.m. 200 William Street.
Fantasy Fest: That Arena Rock Show – October 21
That Arena Rock Show is the ultimate high energy tribute to “Classic” Rock N’ Roll. Performing legendary rock anthems that ruled the airwaves in the 70s and 80s. Including artists like: Led Zeppelin, Aerosmith, AC/DC, Bon Jovi, Guns N Roses to name a few. The free concert takes place at Sunset Pier at 0 Duval Street from 7 to 9 p.m.
10th Annual Witches Ride – Key Largo – October 21
The annual Witches Ride to raise money for the Joey Patterson Memorial Scholarship Fund starts at 1 p.m. with a party at The Catch restaurant, MM 102 oceanside. Registration is $25. Be sure to decorate your bike, golf cart or car and come in your best witch or warlock costume to win prizes. From there, the group travels to the Caribbean Club, MM 104 bayside, for a big backyard bash with food and spooky specialty cocktails.
Key West Artisan Market: Welcome to the Party – October 22
Key West Artisan Market kicks off the fall season with our Welcome to the Party edition to get you ready for a full week of Fantasy Fest costumed festivities. Enjoy coffee, bloody Marys, mimosas, a full bar, smoothies, fresh fruit, and lots of food trucks and food stalls offering delicious meals and snacks. Shop for fresh seafood, fresh Florida produce and arts and crafts, and listen to live musicians. 10 a.m. to 2 p.m. and again from 5 to 7 p.m. in time for the Zombie Ride! Indigenous Park at Higgs Beach, 1801 White Street.
Fantasy Fest: Zombie Bike Ride – October 22
The Rock & Roll costumed Halloween bike ride returns for another wild run on Sunday, Oct. 22. The Zombieland pre-ride party takes place at Fort East Martello from 2 to 6 p.m. with face and body painters, food vendors and a full bar. The ride, with thousands of costumed zombies, rolls out at 6 p.m. going down A-1-A then through downtown. The ride ends with a dance party at the Coffee Butler Amphitheater presented by Rams Head. Register online in advance for $10.
Sheriff’s Animal Farm Open House – October 22
Visit the animals at the farm, including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a capybara, lemur, alpaca, skunk, prairie dog, tortoises and turtles, snakes and many more. It is free of charge, but donations are welcomed because that is how the farm is sustained. The farm is located at 5525 College Rd. on Stock Island at the Sheriff’s Office Headquarters complex. The family-friendly Sheriff’s Animal Farm is open 1 – 3 p.m the second and fourth Sundays of the month.
Fantasy Fest: Heroes and Villians 5k Run/Walk & Hog Roast – October 23
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, 1405 Duval Street. The post-race party is the Official Fantasy Fest Monday Night Party. You can register online for both the race and the post-race Hog Roast and Party, or register separately for either event.
Fantasy Fest: Pirates of the Conch Republic – The Search for Bodacious Booty – October 23
Key West Burlesque presents the sexy, swashbuckling spectacular show starring all of your favorite burlesque performers at Key West Theater, Oct. 23rd through 27th. Doors open at 7; show at 8 p.m. 21 and over only. Tickets $45 to $100. 512 Eaton St.
Fantasy Fest: Pet Masquerade – October 25
The annual Pet Masquerade during Fantasy Fest will see people and their pets in costume strutting their stuff on the stage of the Coffee Butler Amphitheater Wed., Oct. 25. Registration for participants is $25 per category, and starts at 5 p.m. The contest starts at 6:30 p.m. Admission for spectators is free. Food and drinks will be available for purchase. 21 Quay Rd. at Truman Waterfront Park.
39th Annual Key West Headdress Ball – October 26
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 include VIP tables, reserved chair seating and lawn tickets. 21 Quay Rd.
History of Diving Museum: Treasure Treat Night – Islamorada – October 26
Bring the entire family between 5:30 and 7:30 p.m. for a night of haunted exhibits, trick-or-treating through the museum, kids activities and a costume contest with prizes. The costume contest will be at 6:15 p.m. MM 82.9 bayside.
Fantasy Fest: Captain Morgan’s Masquerade March – October 27
Join this hugely popular Fantasy Fest tradition highlighting costumes, creativity and community. The Captain Morgan Masquerade March is a grown-up moving cocktail & dance party that begins at Truman Ave. and Frances St. This moving mosaic of costumed revelers strut their wacky costumes on a route that winds its way north to Fleming Street, stopping at select guest houses, which – while supplies last – hand out complimentary beverages. When you have made your way through Old Town to Duval St., the party isn’t over. Keep on partying at Captain Morgan’s Official Pirate After Party at Kaya Empourium at 618 Duval St., or make your way over to Aqua at 711 Duval St. for their After March Dance Party.
Laura Quinn Wild Bird Sanctuary: Owl-O-Ween Trick or Screech – Key Largo – October 27
Come for some spooky fall festival fun from 4 to 8 p.m. at the annual Owl-O-Ween celebration, including trick or treating, a dunk tank, face painting, a spooky photo-op area, cookie decorating, arts and crafts, a silent auction, a food truck and more. New this year — the Conservation Village featuring local environmental organizations, each with spooky booths and interactive displays. MM 93.6 bayside.
Havana Jack’s: Boo Bash – Marathon – October 27
Get your costume on and come out for one of the biggest costume contests in the Middle Keys, Friday, Oct. 27 at Havana Jack’s. The fun starts at 7 p.m. with live music. The costume contest starts at 8 p.m. 401 E. Ocean Dr., Key Colony Beach.
Fantasy Fest: Bud Light Fantasy Fest Parade – October 28
Join the thousands of exuberant partygoers as this year’s big Bud Light Fantasy Fest Parade rolls down Duval Street beginning at 7 p.m. The parade is a splendid moving party with festive floats, wild walking groups, bicycle brigades, and even human-powered kinetic machines that entertain everyone along the parade route.
Halloween at Pennekamp – Key Largo – October 28
The family-friendly Halloween at Pennekamp event from 5:30 to 8 p.m. features the visitor center aquarium turned into the “A-Scare-Ium,” an outdoor Haunted Trail; Trunk or Treating in the Cannon Beach parking lot from 5:30 to 7:30 p.m.; a costume contest open to both children and adults at 6:30 p.m. and the Captain Coral show at 7:15. The event is free, however donations will be accepted at the park ranger station.
I.Care’s Annual Underwater Critter Costume Party – Islamorada – October 28
Join the I.Care team at Florida Keys Brewing Co. at 6 p..m. for the Underwater Critter Costume Party. Come dressed as your best jellyfish, shark, sea turtle, brain coral or other underwater critter to win some fabulous prizes. There’s also a raffle with more prizes. Proceeds go to help I.Care’s work to replenish and maintain Islamorada-area reefs.
Key West Tropical Forest & Botanical Garden: Screaming Green Halloween – October 28
Kids should come in costume to hunt for tricks and treats along the garden pathways and other secret locations from 10 a.m. to 2 p.m. There’s a costume contest for ages 5 and under at 12:15 p.m. and ages 6 to 12 at 1:15 p.m. There’ll be arts, crafts, games and candy stations throughout the garden. Enjoy this fun and safe Halloween event and learn about how to use recycled items for costumes, decorations, crafts and more. The garden is located at 5210 College Rd.
Amoray Dive Center: Underwater Pumpkin Carving Contest – Key Largo – October 28
Divers become underwater artists as they turn pumpkins into Halloween masterpieces beneath the sea in the Florida Keys National Marine Sanctuary. This year’s carving theme is Mermaids & Sailors. Prizes such as dive trips are awarded to the creator of the most creative jack-o-lantern. Entry fee is $115 per certified diver for the 12:30 p.m. dive trip. Space is limited, contact Amoray Dive Center at 800-426-6729 for reservations and information.
Marathon Community Theatre: Drag Queen Bingo – October 29
This month’s Drag Queen Bingo theme is Gothic Steampunk. Come in your best Gothic or Steampunk costume and battle it out on the runway for the best costume prize. Or, just come as you are for a great time playing bingo. Doors open at 4 p.m. with bingo starting at 5 p.m. $10 admission. 18+ only, ID required at the door. Mile marker 49.5 oceanside.
Green Parrot 49th Annual Haloween Costume Party – October 31
Party at the Parrot on Halloween night with a costume contest and music by the Empire Strikes Brass band, bringing jam, rock and R&B to the Parrot stage. Shows at 9 and 11 p.m. with the party carrying on until 12:30 a.m.
History of Diving Museum: Aquanauts to Astronauts Exhibit – May 20 – December 31, 2023
The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.
Key West Museum of Art & History: Don Pinder – Eyes on the Island – July 14 – November 5, 2023
The Key West Museum of Art & History’s Custom House Museum’s latest exhibition—Don Pinder: Eyes on the Island—is the first exhibition devoted exclusively to the work created by Key West Citizen photographer Don Pinder (1925-2003) during his long career in Key West—including many works never before published or shown. The show, on display through Nov. 5, includes more than 50 black-and-white and color photographs made during his 35-year career of documenting Key West history and culture. 10 a.m. to 5 p.m. daily, 281 Front St.
Scarecrows in the Forest Art Exhibit and Contest – September 1 – November 30, 2023
The Key West Tropical Forest & Botanical Garden is showcasing local artists’, community members’ and local students’ unique versions of the fall season’s Scarecrows in the Tropical Forest. The scarecrows, made from natural and recycled materials, may be discovered throughout the 15-acre garden. The exhibit, open 10 a.m. to 4 p.m. daily, will be a lesson in recycling, art talent and a contest with cash prizes for the entries. The Garden is located at 5210 College Road.
Kids Keys Deals – September 5 – October 15, 2023
The Kids Keys Deals program is in effect through Oct. 15, offering free admission for one child age 12 and under with each paying adult at multiple Keys attractions and excursions in Key West, Marathon and Islamorada. Find the full list of attractions and links to coupons at KidsKeysDeals.com. The program is spearheaded by the Key West Attractions Association.
