The first time we visited Key West in October, we were excited to celebrate Halloween. Little did we know, Halloween isn’t the big event on the island this month. October in the Florida Keys is all about Fantasy Fest, an annual 10-day party that turns Key West into one giant stage for costumes, parades, and pool parties. Think pink costumes, body paint, live music, and fun-loving revelers dancing down Duval Street.
But Fantasy Fest isn’t the only reason October is the perfect time of year to visit. Whether you’re here for outdoor activities, cultural events, or just delicious food like key lime pie, there’s so much to experience.
Key West Weather
When you’re planning your Key West vacation, the weather conditions are always the first question. October brings average high temperatures in the low to mid-80s, with plenty of sunshine and some afternoon thunderstorms. At night, temps dip into the upper 70s—perfect for strolling along the Gulf of Mexico under the stars.
Yes, it’s still hurricane season in the Keys, so flexibility is key. On a given day, you might see quick rain showers (about 12 rainy days this month, totaling over 5 inches of rain). But don’t worry—the showers usually pass, leaving behind sunny days and crystal clear waters.
The water temperature is still warm enough for snorkeling, kayaking, and all kinds of water sports. Many say this is the sweet spot between summer humidity and winter crowds.
Things to do on rainy days in Key West
The best water activities in Key West
Fantasy Fest: Key West’s Biggest Party
If you’re coming to Key West in October, you can’t miss Fantasy Fest. This annual fantasy fest started back in the late fall of 1979 and has grown into one of the island’s most popular events. It’s a mash-up of Mardi Gras and Halloween, with an official theme every year and nonstop entertainment.
Some highlights:
- Zombie Bike Ride – thousands pedal down the island in spooky costumes.
- Bahama Village Goombay Festival – two days of music, cultural activities, and food vendors.
- Captain Morgan Masquerade March – a costumed dance party that winds through Old Town.
- 41st Annual Headdress Ball Pageant – dazzling costumes and theater productions.
- The Enchanted Key West Pet Masquerade – yes, even the pets get to join in.
By the end of the month of October, Duval Street transforms into an entertainment center with live bands, DJs, and plenty of nightlife. It’s chaotic, colorful, and honestly so much fun.
More Things to Do in October
If wild crowds aren’t your vibe, don’t worry—this time of year also offers quieter ways to experience Key West:
- Snorkeling and Water Activities – Explore the coral reef, paddleboard in the Gulf Stream, or take a trip to Dry Tortugas National Park. Book early—spots sell out fast.
- Sunset Cruises – A great way to enjoy live entertainment, delicious food, and vibrant colors over the horizon.
- Outdoor Adventures – With average temperatures still warm, you’ll find ideal conditions for biking, kayaking, or beach lounging. Southernmost Beach Café and Marker Key West Harbor Resort often host a fun pool party or two.
- Cultural Activities – Visit the Key West Historical Society, enjoy theater productions, or wander Bahama Village for local vibes.
- Foodie Fun – October is a great time to explore the island’s restaurants, sip cocktails, and of course, order a slice of key lime pie.
Travel Tips for Visiting in October
- Flights and Getting Around: The Key West International Airport offers nonstop flights from several U.S. cities. Once you’re here, skip the rental car—you can walk, bike, or hop on the Duval Loop bus.
- Driving the Keys: If you’re road-tripping from Miami, give yourself a few days to enjoy Key Largo, Islamorada, and Marathon before reaching Key West. The drive down the Keys is a bucket-list unique way to start your trip.
- Where to Stay: Early October is considered low season, so you’ll find fewer crowds and better deals on Key West vacation homes and resorts. During Fantasy Fest, prices jump into high season levels, so book early. Southernmost Beach Resort is a perfect place if you want to be in the middle of the action.
- Packing Tips: Bring portable speakers for poolside fun, a rain jacket for those surprise showers, and yes—your most outrageous costume if you’re joining the Fantasy Fest dance party.
Why October Might Be the Best Month for Key West
October in Key West is this sweet spot between the humid summer months and the busy winter months. It’s not quite peak season, so you’ll enjoy fewer crowds, better prices, and still have plenty of sunshine for your trip. Whether you’re into nightlife, cultural festivals, or just soaking in the laid-back island vibes, October is truly a wonderful time to visit.
So, is October the best time to experience Key West? For many, yes—it’s when the island comes alive in a way you won’t find any other month. Between the parades, pool parties, and beautiful weather, it’s an adventure you won’t forget.
Ready to plan your trip? Whether you’re here for Fantasy Fest, snorkeling the coral reef, or just chasing sunny weather and key lime pie, October is a great time to fall in love with Key West.
What Not to Miss While in Key West
Ultimate Road Trip from Miami to Key West
Activities During October
Truman Waterfront Farmers Market – Every Thursday – October 2
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Studios of Key West: First Thursday Open House – October 2
Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!
Fall Backcountry Fly Championship – October 3-4, 2025
Islamorada. Tournament anglers compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals one 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. Visit BFCtournament.com.
Art Xperience Featuring William DeBilzan – October 3-5, 2025
Enjoy an exclusive art exhibition and fashion show night with hors d’oeuvres and drinks, plus an expressive painting class inspired by William DeBilzan’s work. This special experience also includes a four-course dinner with wine pairings by a guest chef, daily breakfast for two, 20% off treatments at Ocean Spa, and a spacious room with a welcome amenity.
Expressive Painting Class Inspired by William DeBilzan’s Work – October 4
In a relaxed and welcoming environment, you’ll explore DeBilzan’s signature style—characterized by bold colors, elongated figures, and themes of love, identity, and connection—and create your own interpretation on canvas. No prior experience needed!
This is not your typical paint night—it’s an artful experience that invites you to connect with the emotional depth and storytelling behind DeBilzan’s work.
Exclusive 4-Course Dinner Featuring Guest Chef Ken Shiro Lumpkin – October 4
Experience a night where fine art meets fine dining in this unforgettable culinary event inspired by the bold and emotional work of artist William DeBilzan.
Under the open sky, guests will enjoy a 4-course dinner crafted in collaboration with the renowned guest chef Ken Shiro Lumpkin, whose culinary artistry mirrors the creativity and storytelling found in DeBilzan’s Caribbean-influenced paintings.
This is more than dinner—it’s a curated celebration of art, flavor, and story, designed to leave a lasting impression.
Splash Into a New Era! Taylor Swift Album Release Party – October 5
Dive into the ultimate Taylor Swift Album Release Party in the Florida Keys! Celebrate with fellow Swifties, enjoy themed drinks, dance to her latest hits, and make unforgettable memories by the ocean. Don’t miss this splashy night of music, fun, and friendship
Truman Waterfront Farmers Market – Every Thursday – October 9
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
War of the Worlds – October 9
THE KEY PLAYERS WELCOME YOU TO COMMUNITY THEATER IN THE UPPER KEYS
The Key Players is the premier theatrical troupe presenting live theater in the Upper Keys. Our community theater is a non-profit organization, established in 1978, to perform plays and shows written by established playwrights for residents and visitors of the Upper Keys in Monroe County, Florida. We perform musicals, comedies and dramatic plays that have been produced on Broadway, Off Broadway, and in Regional Theaters around the world.
We perform at various venues around the Upper Keys, including the Murray E. Nelson Government and Cultural Center. Our staff, crew, and cast members are professionals in the community, from varied backgrounds; many who have produced, directed and/or acted professionally, and who are eager to keep the tradition of community theater alive and thriving in the Upper Keys.
STACK’D WEEKEND: Key West Music Festival – October 10
STACK’D WEEKEND Music Festival Oct. 10 – 12, 2025
Founded by Key West’s own Mike Stack, the artist behind the song “I’m from Key West” and many more, the STACK’D WEEKEND Music Festival is not just a music festival — it’s a three-day, 8 event, island escape where hip hop, country, reggae, and more come together in Key West. You’ll feel like a local, even if it’s your first time here. We’ll have live shows, DJ sets, and parties on the island throughout the weekend— The venues include pools, bars, and the iconic Sunset Pier. STACK’D WEEKEND is where music meets island energy. Where you’ll see some of your favorite artists and party with a crowd that came to let loose and enjoy the moments.. It’s the ultimate weekend — no
stress, good times, cold drinks, and nonstop music. Whether you’re barhopping, poolside, or in the middle of the crowd at the main stage, this is the kind of weekend you’ll be talking about all year. This isn’t your typical festival.
This is STACK’D WEEKEND — and you don’t want to miss it!
View the lineup here: stackdweekend.com/artists
War of the Worlds – October 10
THE KEY PLAYERS WELCOME YOU TO COMMUNITY THEATER IN THE UPPER KEYS
The Key Players is the premier theatrical troupe presenting live theater in the Upper Keys. Our community theater is a non-profit organization, established in 1978, to perform plays and shows written by established playwrights for residents and visitors of the Upper Keys in Monroe County, Florida. We perform musicals, comedies and dramatic plays that have been produced on Broadway, Off Broadway, and in Regional Theaters around the world.
We perform at various venues around the Upper Keys, including the Murray E. Nelson Government and Cultural Center. Our staff, crew, and cast members are professionals in the community, from varied backgrounds; many who have produced, directed and/or acted professionally, and who are eager to keep the tradition of community theater alive and thriving in the Upper Keys.
Lower Keys Rotary Annual Haunted House – October 10 -12, 2025
We’re back for another spooktacular event at Big Pine Community Park. This year’s theme…Hollywood Horrors! Volunteer, sponsor a room, or come on out for another great event hosted by Lower Keys Rotary!
October 11th US Navy Anniversary Tours – October 11
Join the History of Diving Museum at 11 AM and 2 PM for a special guided tour of the exhibits! The tour is included in your admission price. October’s tours will coincide with the 250th anniversary of the US Navy, and feature highlights of military divers and their heroic, often dangerous work.
War of the Worlds – October 11
THE KEY PLAYERS WELCOME YOU TO COMMUNITY THEATER IN THE UPPER KEYS
The Key Players is the premier theatrical troupe presenting live theater in the Upper Keys. Our community theater is a non-profit organization, established in 1978, to perform plays and shows written by established playwrights for residents and visitors of the Upper Keys in Monroe County, Florida. We perform musicals, comedies and dramatic plays that have been produced on Broadway, Off Broadway, and in Regional Theaters around the world.
We perform at various venues around the Upper Keys, including the Murray E. Nelson Government and Cultural Center. Our staff, crew, and cast members are professionals in the community, from varied backgrounds; many who have produced, directed and/or acted professionally, and who are eager to keep the tradition of community theater alive and thriving in the Upper Keys.
Rams Head Presents: Peter Antoniou: Psychic Comedian – October 11
From amazing the judges on America’s Got Talent, to headlining in Las Vegas, to selling out shows in London’s West End, Peter Antoniou’s mind reading skills have astounded audiences around the globe. Combining razor-sharp British wit with a stunning ability to know exactly what you are thinking, Peter’s shows are interactive and unforgettable. Join him as he reads minds and tickles funny bones, telling jokes and fortunes live onstage.
Southernmost Half Marathon & 10K – October 12
What better place for a race vacation than the tropical splendor of Key West! Whether it is just a weekend getaway or a full-blown vacation, you can go wrong in Key West and Run Conch Republic, the home of the Southernmost Half Marathon & 10K run.
Sheriff’s Animal Farm Open House – October 12
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Free Immerse Yourself! Marine Habitat Updates & Missions – October 15
Islamorada: Join the History of Diving Museum as it hosts Kristopher Benson of NOAA. He will take us through the recent advances made in the field of underwater habitats, and what sort of research they take part in. Presentation will be both in-person and virtual, and take place at 7 PM on October 15th at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Be sure to come early for the Museum’s extended hours and see Celebrating 20 Years! Featured Exhibit. Donations welcome. Info: (305) 664-9737; www.divingmuseum.org
The Wizard of Oz – October 15
Follow the yellow brick road in this delightful stage adaptation of L. Frank Baum’s beloved tale, featuring the iconic musical score from the MGM film. The timeless tale, in which young Dorothy Gale travels from Kansas over the rainbow to the magical Land of Oz, continues to thrill audiences worldwide.
Truman Waterfront Farmers Market – Every Thursday – October 16
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
REEF Fest – October 16
Join us for REEF Fest! October 16-19, 2025 in Key Largo, Florida
REEF Fest 2025 registration is now open! We hope you will join us for the 10th anniversary of this event. If you haven’t attended REEF Fest before and are curious, check out the photo album from REEF Fest 2024 here. You can also view recordings of past REEF Fest seminars on YouTube.
REEF has hosted REEF Fest ocean-themed seminars and social events in the Florida Keys each fall since 2015. Divers, snorkelers, and ocean lovers attend REEF Fest to celebrate their love of marine life and learn about the latest in conservation — with plenty of time for Florida Keys adventures that bring those lessons to life! If you have any questions, please contact events@REEF.org.
Morada Way Third Thursday Art Walk – October 16
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. 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 at 151 Morada Way.
Walk on White Art Celebration – October 16
Walk on White, one of Key West’s most popular monthly art strolls, kicks off its 2025/2026 season on October 16 and continues monthly on every third Thursday through May, from 6:00–9:00 p.m. Centered along White Street from Southard to United, the event showcases local galleries, studios, and businesses featuring visual art, live performances, creative demos, and refreshments. Now also a platform for supporting local nonprofits, this season’s opening night includes a special performance by the Key West High School Band and a fundraiser raffle benefiting their upcoming trip to Rome. For full event details and participating venues, visit www.WalkOnWhiteKeyWest.com.
War of the Worlds – October 16
THE KEY PLAYERS WELCOME YOU TO COMMUNITY THEATER IN THE UPPER KEYS
The Key Players is the premier theatrical troupe presenting live theater in the Upper Keys. Our community theater is a non-profit organization, established in 1978, to perform plays and shows written by established playwrights for residents and visitors of the Upper Keys in Monroe County, Florida. We perform musicals, comedies and dramatic plays that have been produced on Broadway, Off Broadway, and in Regional Theaters around the world.
We perform at various venues around the Upper Keys, including the Murray E. Nelson Government and Cultural Center. Our staff, crew, and cast members are professionals in the community, from varied backgrounds; many who have produced, directed and/or acted professionally, and who are eager to keep the tradition of community theater alive and thriving in the Upper Keys.
“Ladies, Let’s Go Fishing!” Florida Keys Saltwater Seminar and Fishing Fever Inshore/Offshore Tournament – October 17 – 19, 2025
Islamorada. Female fishing fans can learn or polish angling skills during the award-winning weekend seminar with two days of optional charter fishing and the Fishing Fever Fun Tournament. More than 9,000 female graduates have immersed themselves in the lighthearted yet skill-heavy curriculum to learn and hone abilities in offshore, bottom, inshore and fly fishing. Visit ladiesletsgofishing.com or email fish@ladiesletsgofishing.com.
Casting for Cats Backcountry Tournament – October 17
Islamorada. This formerly all-female tournament now has a co-ed division and a women’s division. Anglers earn points for catching bonefish, permit, tarpon, snook and redfish using bait, artificial lures or fly tackle. Points are also awarded for ladyfish, sharks, jacks and spotted sea trout. The event is a major fundraiser to help control the feral cat population in the Upper Keys. Call Sharon Mahoney Ellenwood at 305-664-2012.
Key West Fantasy Fest – October 17 – 26, 2025
“Bedtime Stories & Magical Monsters” is the official theme for Fantasy Fest 2025, Key West’s annual multi-day costuming extravaganza in paradise. From October 17-26, revelers can explore an array of exciting events, including the the exuberant Goombay Festival in the streets, the Zombie Bike Ride, a Bedtime Stories and Magical Monsters-themed 5K run/walk, the Captain Morgan Masquerade March (aka “Locals Parade”), the Royal Coronation of the 2025 Fantasy Fest King and Queen, plus concerts, theater productions, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and the world-famous Key West Fantasy Fest Parade on Saturday, Oct. 25.
Fantasy Fest: Zombie Bike Ride October 19
The annual Rock n’ Roll costumed Zombie bike ride returns for another wild run on Sunday, Oct. 19. The Zombieland pre-ride party takes place at Fort East Martello, 3501 S. Roosevelt, 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 at Truman Waterfront Park presented by Rams Head. Register online in advance for $10.
Truman Waterfront Farmers Market – Every Thursday – October 23
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Treasure Treat Night! – October 23
Islamorada: Join the History of Diving Museum for its fourth annual Treasure Treat Night! The event starts at 5:30 PM on Thursday, October 23rd, and ends at 7 PM. Venture through the Museum’s haunted exhibits, collect candy, and show off your spookiest costumes at the costume contest at 6:15 PM. The top three contestants will win fun prizes, and everyone gets to go home with candy and kids’ activities. Event takes place at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). This event is free, with donations welcome. Info: (305) 664-9737; www.divingmuseum.org
Fantasy Fest: Masquerade March October 24
Join the hugely popular Fantasy Fest tradition known as the locals’ parade that highlights costumes, creativity and community. The Captain Morgan Masquerade March is a grown-up moving cocktail and dance party that begins at 5:30 p.m. at Truman Ave. and Frances St. The route winds its way north to Fleming St., stopping at participating guest houses that hand out complimentary beverages.
Fantasy Fest Parade – October 25
Join 70,000 exuberant partygoers as the Key West Fantasy Fest parade rolls down Duval Street featuring glittering floats, spectacular costumes and dazzling dancing groups, some dressed and decorated to illuminate this year’s theme of “Bedtime Stories & Magical Monsters.” It doesn’t get any wilder than this! Parade steps off at 7 PM; Free to attend for spectators.
Sheriff’s Animal Farm Open House – October 26
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Key West Bear Weekend 2025 – October 29 – November 2, 2025
Key West Bear Weekend is back for 2025! After an amazing 2024, come back to the friendliest bear event ever in the beautiful paradise island of Key West. From pool parties to party nights, and shopping experiences to dinners, there’s something for everyone! Check out the full schedule at https://www.keywestbearweekend.com/events
Truman Waterfront Farmers Market – Every Thursday – October 30
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Gathering of the Order of the Sleepless Knights – October 31
The 2025 Tours are ready to be announced. Last years tours were amazing. More than just 2 may be added this year.
The Order of the Sleepless Knights is excited to announce another exclusive event for 2025. A private charter has been reserved through the Conch Train Historic Tour Company for a special Order of the Sleepless Knights tour through Old Town Key West. The tour will visit 35 locations significant to Jimmy Buffett’s life and career in Key West, including places where he lived, played some of his first shows, referenced in his songs, and other historical sites related to Buffett.
The Order of the Sleepless Knights Tour will take place on Friday, October 31st and Saturday, November 1st(Already Sold Out!!), starting at 10:00 AM and concluding at noon at Island Dogs for the show on Saturday. Friday it ends at a to be determined location. David Hamm will serve as the guide, narrating details about each of the 35 locations, sharing their history, and explaining the connections to Buffett’s music.
The tour will start at the Conch Train Store, located at 501 Front Street, and will travel through Old Town to these iconic locations. At the end of the tour on Saturday, participants will be dropped off at Island Dogs on Front Street, for the start of a Hungry Hard Luck Heroes show. There is a Fat Tuesday near the starting point, providing an opportunity for attendees to grab a beverage before the tour begins. On Friday the tour ends at Captain Tony’s where you can walk over and take a Stroll down Duval street and continue your fun while your Trop Rock’N Duval.
There are 50 available seats, and the cost is $25.00 per person, with gratuity for the driver included. Additional tipping is welcome but not required. To sign up for the tour, participants are asked to comment and tag David Hamm to indicate how many seats they will be reserving, or send him a direct message through Facebook Messenger.
Payments can be made via Venmo (@David-Hamm-23), PayPal (@davidhamm1), or Zelle (details available via direct message). Seats are expected to sell out quickly, so it is encouraged to reserve a spot soon. Updates on availability will be provided.
History of Diving Museum Presents – Celebrating 20 Years! Featured Exhibit – until December 31, 2025
The History of Diving Museum’s new limited-time featured exhibit is open to the public! Starting May 21st, dive into the Museum’s 20th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org
Taste The Keys – October 2025
All October, find foodie paradise in Key Largo with select restaurants serving prix fixe menus, plus two exclusive Taste the Keys Trolley Tours featuring progressive dining on wheels. Savor fresh seafood, steaks, Italian favorites and desserts and vote in the Signature Dish Showdown. From October 1–31, savor every bite at participating restaurants offering specially crafted lunch and dinner menus — all at a great value. Adding to the excitement, Taste the Keys Trolley Tours take place October 2 and 16. These progressive dining excursions stop at four featured restaurants where guests enjoy sample-sized dishes, each paired with a signature drink or glass of wine. Trolley tickets are $125 per person and include all food, beverages, and transportation.
