KEY WEST IN OCTOBER 2026 — WEATHER, WHAT TO EXPECT & EVENTS
KEY WEST IN OCTOBER 2026 — WEATHER, WHAT TO EXPECT & EVENTS
Heading to Key West this October? October is a fun time to visit, with warm weather, plenty happening around the island and one of Key West’s biggest events of the year — Fantasy Fest!
WHAT IS THE WEATHER LIKE IN KEY WEST IN OCTOBER?
October is still part of Key West’s rainy season, so expect warm, humid tropical weather with a mix of sunshine, clouds and passing showers or thunderstorms.
Temperatures are typically in the 80s during the day with warm evenings, so you’ll still want shorts, sundresses, sandals and plenty of sunscreen.
Don't panic if your weather app shows rain every day! During rainy season, a rain icon does not necessarily mean an all-day washout. Key West often gets periods of sunshine mixed with passing tropical showers.
That said, October weather can occasionally bring stretches of heavier rain, so no forecast is a guarantee. Keep an eye on the forecast as your trip gets closer.
Rainy season generally runs June through October, with November beginning the transition into Key West’s drier season.
IS OCTOBER GOOD FOR BOATING?
Absolutely, boating is one of the best ways to experience Key West! Sandbar trips, snorkeling, fishing and sunset cruises are all popular in October.
As always, conditions on the water depend on the wind and weather that particular day, so charter captains will make the call based on actual conditions.
WHAT SHOULD I PACK?
Key West is VERY casual. Pack light, comfortable clothes and don't overthink it!
Bring:
• Shorts, tanks, T-shirts and sundresses
• Comfortable sandals or walking shoes
• Swimsuits
• Sunscreen
• Sunglasses and a hat
• A lightweight rain jacket or poncho
• Costumes if you're visiting during Fantasy Fest!
WHAT IS KEY WEST LIKE IN OCTOBER?
The beginning of October can still have more of that slower off-season Key West feel, but that changes dramatically as Fantasy Fest approaches.
Fantasy Fest runs October 16–25, 2026, and during that time the island gets BUSY.
Expect packed bars and restaurants, elaborate costumes everywhere, street parties, live music, road closures and a completely different atmosphere in Old Town.
The final Fantasy Fest weekend — particularly Friday, October 23 and Saturday, October 24 — is one of the busiest periods of the month.
A NOTE FOR FAMILIES
Key West is still a destination families can enjoy during October, and events like Goombay Festival, Children’s Day and the Artisan Market are family-friendly.
However, Fantasy Fest itself can become very adult-oriented, particularly around Duval Street and downtown at night. If you're traveling with children during Fantasy Fest, research individual events and plan accordingly.
GETTING AROUND DURING FANTASY FEST
If you're staying in Old Town, walking or biking is usually your best option.
Expect road closures and very limited parking around downtown during the major Fantasy Fest events. If you're staying outside Old Town, consider using a taxi, rideshare or public transportation rather than trying to find parking near Duval Street.
OCTOBER SCHEDULE 2026
OCTOBER 1–5 — KEY WEST oktoBREWfest
Southernmost Beach Resort, 1319 Duval Street + participating locations around Key West
Key West’s annual beer celebration returns with several days of events, tastings and specials around the island.
Grand Tasting — Saturday, October 3
3–8 PM
Southernmost Beach Resort
The Grand Tasting is the centerpiece of oktoBREWfest, bringing together beer selections, food, entertainment and plenty of island fun.
OCTOBER 15 — WALK ON WHITE
6–8 PM
White Street Gallery District — centered around 1102 White Street
FREE
Explore galleries, artist studios and local businesses throughout the White Street district. Expect exhibition openings, artist demonstrations, locally made art, special events and refreshments.
OCTOBER 15–23 — HEDWIG AND THE ANGRY INCH
Waterfront Playhouse, 407 Wall Street at Mallory Square
Ticketed event
The Waterfront Playhouse opens its season with an encore presentation of Hedwig and the Angry Inch, presented as a live rock-concert-style theatrical experience.
OCTOBER 16–25 — FANTASY FEST 2026
Events throughout Key West
2026 Theme: Musical Icons and Iconic Musicals
Fantasy Fest is Key West’s legendary 10-day celebration filled with elaborate costumes, parties, parades, live entertainment and some truly only-in-Key-West events.
Some Fantasy Fest events are family-friendly, while others are strictly geared toward adults.
OCTOBER 16 & 17 — BAHAMA VILLAGE GOOMBAY FESTIVAL
12 PM–12 AM both days
Bahama Village — Petronia Street
Main stage: Petronia & Emma Streets
FREE
Family-friendly
Celebrate Key West’s Bahamian and Caribbean heritage with live reggae and soca music, Caribbean food, arts, crafts, vendors and entertainment throughout Bahama Village.
OCTOBER 16 — FANTASY FEST ROYAL CORONATION
Doors: 6 PM
Show: 7 PM
Coffee Butler Amphitheater, 21 Quay Road at Truman Waterfront
Ticketed event
Watch the crowning of the 2026 Fantasy Fest King and Queen following weeks of fundraising benefiting the Florida Keys SPCA.
OCTOBER 18 — ZOMBIE BIKE RIDE
Begins near Fort East Martello, 3501 S. Roosevelt Boulevard - Starts at 6:00PM
One of Key West’s biggest Fantasy Fest traditions! Thousands of costumed zombies take to their bikes for the ride along the Atlantic side of Key West and toward downtown.
Come dressed as a zombie, decorate your bike or just find a spot along the route and watch!
OCTOBER 18 — KEY WEST ARTISAN MARKET: FANTASY FEST EDITION
10 AM–2 PM
Higgs Beach, 1707 White Street at Atlantic Boulevard
FREE
Shop Florida Keys artists and makers, find Fantasy Fest merchandise and enjoy food vendors, adult beverages and live music.
OCTOBER 18 — LEGENDS NEVER DIE: DÍA DE LOS MUERTOS CELEBRATION OF MUSICAL ICONS
3–7 PM
Elevate Skye Bar & Lounge at Opal Key Resort & Marina
A Día de los Muertos celebration honoring musical legends with Latin- and Mexican-inspired drinks, food, art, dancing and music.
OCTOBER 19 — FANTASY FEST 5K RUN/WALK
Downtown Key West
Run, walk and dress up for this annual Fantasy Fest tradition through Key West. Costumes are definitely encouraged!
OCTOBER 19 — MARILYN MONROE MONDAY MARATHON
10 AM–10 PM
Costume contest: 7 PM
Tropic Cinema, 416 Eaton Street
Spend the day celebrating one of Hollywood’s biggest icons with Marilyn Monroe classics and a costume contest in the evening.
OCTOBER 20 — TUTU TUESDAY
Check-in/pre-party begins: 4:30 PM
Festivities/parade begin around 6 PM
Mary Ellen’s, 420 Appelrouth Lane + Caroline Street district
One of Fantasy Fest’s most recognizable traditions. Put on a tutu and head downtown for an evening of costumes, DJs, drinks and parties.
OCTOBER 21 — PET MASQUERADE
Registration: 5 PM
Show: 6:30 PM
Coffee Butler Amphitheater at Truman Waterfront, 21 Quay Road
FREE to watch | Fee to enter a pet
Pets and their humans take the stage in some seriously creative costumes. Categories include Pet/Owner Lookalike, Most Exotic, Best Theme Adaptation and more.
OCTOBER 21 — SCHOONER WHARFSTOCK
7 PM–Midnight
Costume judging: 8:30 PM
Schooner Wharf Bar, 202 William Street
FREE
Break out the tie-dye and flower power for a Woodstock-inspired night of music, costumes and prizes.
OCTOBER 22 — PINK PARTY
Starts at 8 PM
Fat Tuesday, 305 Duval Street
Wear PINK for this longtime Fantasy Fest tradition featuring music, entertainment and plenty of costumes.
OCTOBER 23 — FANTASY FEST STREET FAIR & COSTUME PROMENADE
Arts & crafts: 12–10 PM
Food: 12 PM–2 AM
Duval Street
Duval Street transforms into a huge pedestrian celebration with food, drinks, arts, crafts, costumes and entertainment.
OCTOBER 23 — CAPTAIN MORGAN MASQUERADE MARCH
Paparazzi Row pre-party: 4 PM
Fleming & White Streets
Lineup: 5 PM
Frances & Petronia Streets
March begins: 5:30 PM
Better known locally as the Locals’ Parade, this is one of my favorite Fantasy Fest traditions!
Costumed groups make their way through Old Town before joining the Fantasy Fest Street Fair festivities downtown.
OCTOBER 24 — FANTASY FEST STREET FAIR
Begins at Noon
Duval Street
Parade day starts early! Food vendors, drinks, costumes and entertainment take over downtown before the big parade that evening.
OCTOBER 24 — DEEP EDDY VODKA FANTASY FEST PARADE
7 PM
Downtown Key West / Duval Street
THIS is the big one!
Elaborate floats, incredible costumes, walking groups, bicycle brigades and thousands of spectators fill downtown Key West for the signature event of Fantasy Fest.
The parade winds through downtown and along world-famous Duval Street.
OCTOBER 25 — CHILDREN’S DAY
12–5 PM
Bayview Park, 1320 Truman Avenue
Family-friendly
A great Fantasy Fest event for families featuring rides, games, food, arts and crafts, entertainment and a children’s costume contest.
OCTOBER 25 — MONROE COUNTY SHERIFF’S ANIMAL FARM OPEN HOUSE
1–3 PM
5501 College Road, Stock Island
FREE; donations welcomed
Family-friendly
Visit rescued and adopted animals including horses, goats, pigs, birds, reptiles and other exotic animals. A great activity if you're visiting with kids!
OCTOBER 27 — GARRISON KEILLOR & ERICA RHODES
Doors: 7 PM
Show: 8 PM
Key West Theater, 512 Eaton Street
Ticketed
Garrison Keillor and comedian Erica Rhodes bring The Crazy Uncle and His Sensible Niece to the Key West Theater.
OCTOBER 29 — SUNNY JIM: CAYMAN DAYS
Doors: 3 PM
Show: 4 PM
Key West Theater — Back Stage Listening Room, 512 Eaton Street
Ticketed
Part of a run of Trop Rock-inspired performances closing out October at the Key West Theater.
OCTOBER 30 — SUNNY JIM: FLORIDA DAYS
Doors: 12 PM
Show: 1 PM
Key West Theater — Back Stage Listening Room
OCTOBER 30 — WILL KIMBROUGH
Doors: 4 PM
Show: 5 PM
Key West Theater, 512 Eaton Street
OCTOBER 30 — BUFFETT THROUGH THE YEARS
Doors: 7 PM
Show: 8 PM
Key West Theater, 512 Eaton Street
A musical celebration inspired by the songs and legacy of Jimmy Buffett.
OCTOBER 31 — HALLOWEEN IN KEY WEST
Downtown Key West & Duval Street
Various times and locations
Fantasy Fest may be over, but Key West definitely isn’t finished dressing up! Expect Halloween costumes, live music and parties throughout downtown.
OCTOBER 31 — TEXAS TROP ROCK
Doors: 12 PM
Show: 1 PM
Key West Theater, 512 Eaton Street
Featuring Jerry Diaz, Dan Sullivan and the Jonas Lorence Band.
OCTOBER 31 — JIM MORRIS TRIBUTE
Doors: 6 PM
Show: 7 PM
Key West Theater, 512 Eaton Street
Sunny Jim, John Patti and Jimi Pappas come together for a tribute to Jim Morris.
EVERY EVENING — MALLORY SQUARE SUNSET CELEBRATION
Begins approximately two hours before sunset
Mallory Square
FREE
Head to Mallory Square for local artists, street performers, food vendors and one of Key West’s most famous traditions while watching the sun set over the Gulf.
VISITING DURING FANTASY FEST?
Fantasy Fest runs October 16–25, 2026, and downtown Key West gets VERY busy, particularly during the final weekend.
Expect road closures, limited parking and heavier traffic around Old Town and Duval Street. Walking, biking or using local transportation is usually much easier than trying to drive downtown during the biggest events.
Some Fantasy Fest events are family-friendly, while others are intended for adults, so always check the individual event before bringing children.
MORE OFFICIAL FANTASY FEST INFO
Follow Experience Key West for local tips, upcoming events and things to do around the island!