Sun Mon Tue Wed Thu Fri Sat
1
World War II-Era Middle Keys Airport to Celebrate 75 Years of Service 5:28 pm
World War II-Era Middle Keys Airport to Celebrate 75 Years of Service
Oct 1 @ 5:28 pm – 6:28 pm
A vital Middle Keys airways connection to the mainland, the Florida Keys Marathon International Airport is to recognize 75 years of service in a family-friendly celebration set for Saturday, Oct. 20, in Marathon.N
2
Scenic Key Largo Bridge Run Returns Nov. 10 11:30 am
Scenic Key Largo Bridge Run Returns Nov. 10
Oct 2 @ 11:30 am – 12:30 pm
Hundreds of foot racers are to experience the panorama above the Upper Keys and the eastern edges of the Florida Everglades in the annual First State Bank Key Largo Bridge Run set for Saturday, Nov. …

Scenic Key Largo Bridge Run Returns Nov. 10 Read More »

Key West’s Goombay Festival to Blend Music, Food and Island Spirit 1:49 pm
Key West’s Goombay Festival to Blend Music, Food and Island Spirit
Oct 2 @ 1:49 pm – 2:49 pm
High-energy family fun, entertainment and multicultural taste treats await revelers Friday and Saturday, Oct. 19-20, during the annual Goombay street festival.N
3
American Airlines to Launch First Nonstop Service Between Philadelphia and Key West 10:07 am
American Airlines to Launch First Nonstop Service Between Philadelphia and Key West
Oct 3 @ 10:07 am – 11:07 am
American Airlines is to launch nonstop service between Philadelphia, Pennsylvania, and Key West International Airport (EYW) — the first between the two cities — and from Chicago, Illinois, into Key West in February for spring …

American Airlines to Launch First Nonstop Service Between Philadelphia and Key West Read More »

Outrageous Parade to Highlight Key West’s Fantasy Fest Oct. 27 3:59 pm
Outrageous Parade to Highlight Key West’s Fantasy Fest Oct. 27
Oct 3 @ 3:59 pm – 4:59 pm
Flamboyant festivity is the name of the game during the Bud Light Fantasy Fest Parade set for the night of Saturday, Oct. 27. The lavish procession is the highlight of Key West’s Oct. 19-28 Fantasy …

Outrageous Parade to Highlight Key West’s Fantasy Fest Oct. 27 Read More »

United Airlines to Launch Year-Round Daily Service to Key West from Newark Liberty International Airport 5:31 pm
United Airlines to Launch Year-Round Daily Service to Key West from Newark Liberty International Airport
Oct 3 @ 5:31 pm – 6:31 pm
Beginning Oct. 4, United Airlines is to offer year-round daily nonstop service to Key West from New Jersey’s Newark Liberty International Airport on United Express 70-seat Embraer E170 regional jets.N
4
5
SoMo Marathon & Half Marathon
SoMo Marathon & Half Marathon
Oct 5 – Oct 7 all-day
This event is one of a kind! Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half promises just that- 26.2 or 13.1 …

SoMo Marathon & Half Marathon Read More »

6
7
8
Lady Anglers to Learn and Fish at Keys’ ‘No-Yelling School’ Weekend Oct. 19-21 4:29 pm
Lady Anglers to Learn and Fish at Keys’ ‘No-Yelling School’ Weekend Oct. 19-21
Oct 8 @ 4:29 pm – 5:29 pm
The no-experience-necessary “Ladies, Let’s Go Fishing!” girls’ getaway provides female anglers the chance to learn, network and enjoy some tournament competition Friday through Sunday, Oct. 19-21, in the sport fishing capital of Islamorada.N
9
Florida Keys Angler Sweeps Baybone Celebrity Tournament 1:19 pm
Florida Keys Angler Sweeps Baybone Celebrity Tournament
Oct 9 @ 1:19 pm – 2:19 pm
Brooke Black was named grand champion angler at the 28th annual Robert-James Sales Baybone Celebrity Tournament that ended Oct. 7 in Islamorada.N
Grand Vin – Tuscan Wine Tasting 6:30 pm
Grand Vin – Tuscan Wine Tasting
Oct 9 @ 6:30 pm – 9:30 pm
Tuesday, October 9th Tuscan Wine Tasting, 6:00 pm – 7:30 pm Vinos on Duval 810 Duval Street Join us at Vinos as Luciano from Banfi Wines tastes some fabulous Tuscan Wines with us! Free Tasting
10
Islamorada Sailfish Tournament to Begin Florida Keys Gold Cup Sailfish Championship 11:18 am
Islamorada Sailfish Tournament to Begin Florida Keys Gold Cup Sailfish Championship
Oct 10 @ 11:18 am – 12:18 pm
For over 50 years, the Islamorada Sailfish Tournament has opened the renowned triple-crown Florida Keys Gold Cup Sailfish Championship series. This year’s event dates are Thursday through Sunday, Nov. 29 through Dec. 2.N
11
Welcome the Holiday Season at Lower Keys Island Art Festival 11:10 am
Welcome the Holiday Season at Lower Keys Island Art Festival
Oct 11 @ 11:10 am – 12:10 pm
Santa might wear shorts in the subtropical Lower Florida Keys, and palm trees might outnumber Christmas trees, but holiday lovers can find plenty of seasonal spirit amid the area’s balmy breezes and warm temperatures.N
12
International Sand Art Competition to Bring Master Sculptors to Key West 11:32 am
International Sand Art Competition to Bring Master Sculptors to Key West
Oct 12 @ 11:32 am – 12:32 pm
High-energy creativity, unique “art supplies” and playful beachside fun characterize the International Sand Art Competition, set to provide an intriguing experience for spectators over Thanksgiving weekend in Key West.N
Grand Vin Wine Event – Riddle Me This…Jesse’s Magical Masquerade 6:00 pm
Grand Vin Wine Event – Riddle Me This…Jesse’s Magical Masquerade
Oct 12 @ 6:00 pm – 8:00 pm
Friday, October 12th Riddle Me This…Jesse’s Magical Masquerade 6:00 pm – 8:00 pm Grand Vin 1107 Duval This week’s host is Jesse from Southern Wine, and she will be tempting us with some scarily good …

Grand Vin Wine Event – Riddle Me This…Jesse’s Magical Masquerade Read More »

13
14
Wine Bingo! Vino’s on Duval St. 7:30 pm
Wine Bingo! Vino’s on Duval St.
Oct 14 @ 7:30 pm – 9:30 pm
Wednesday, Wednesday 14th Wine Bingo! 7:30 pm – 9:30 pm $1.00 per card, 5 games Vinos on Duval 810 Duval Street Come join us as we play Bingo with a twist. Instead of numbers we …

Wine Bingo! Vino’s on Duval St. Read More »

15
Divers Carve Pumpkins Underwater in Florida Keys 10:36 am
Divers Carve Pumpkins Underwater in Florida Keys
Oct 15 @ 10:36 am – 11:36 am
With their favorite marine creatures in mind, a creative group of scuba divers submerged 30 feet beneath the surface in the Florida Keys National Marine Sanctuary to pare subsea jack-o-lanterns — all competing in the …

Divers Carve Pumpkins Underwater in Florida Keys Read More »

16
17
18
Spencer’s Fall Wine Dinner 6:30 pm
Spencer’s Fall Wine Dinner
Oct 18 @ 6:30 pm – 9:30 pm
Thursday, October 18th Spencer’s Fall Wine Dinner 6:30 pm – 9:30 pm $85.00 per person Spencer’s By The Sea, Key West 1435 Simonton St. Join us in celebrating the flavors of Fall! Spencer’s monthly Wine …

Spencer’s Fall Wine Dinner Read More »

19
Key West Burlesque presents: Madame DuJour’s Magical Game Show Experience 8:00 pm
Key West Burlesque presents: Madame DuJour’s Magical Game Show Experience @ Waterfront Playhouse
Oct 19 @ 8:00 pm – Oct 26 @ 10:00 pm
Ladies and Gentlemen, come on down! You’re the next contestants on Madame DuJour’s Magical Game Show and Burlesque Experience! An astonishing, interactive event awaits as Key West Burlesque and world renowned magician, Nick Locapo, take …

Key West Burlesque presents: Madame DuJour’s Magical Game Show Experience Read More »

39th Annual Key West Fantasy Fest
39th Annual Key West Fantasy Fest
Oct 19 – Oct 28 all-day
39th Annual Key West Fantasy Fest
This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a headdress ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.  …

39th Annual Key West Fantasy Fest Read More »

Goombay Festival
Goombay Festival
Oct 19 – Oct 20 all-day
Held in Key West’s historic Bahama Village neighborhood, the lively 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 …

Goombay Festival Read More »

Florida Keys Conservation a Priority for Generations 1:49 pm
Florida Keys Conservation a Priority for Generations
Oct 19 @ 1:49 pm – 2:49 pm
For more than 100 years, the Florida Keys’ richly diverse natural environment has been recognized and protected by foresighted conservation efforts. The Keys’ four national wildlife refuges and the Florida Keys National Marine Sanctuary foster …

Florida Keys Conservation a Priority for Generations Read More »

20
Celebrate 75 Years of Aviation at Marathon Airport!
Celebrate 75 Years of Aviation at Marathon Airport!
Oct 20 all-day
Celebrate 75 Years of Aviation at Marathon Airport!
Fly or drive to the celebration! This free-admission event from 9 a.m. to 5 p.m. is to commemorate 75 years of aviation in the heart of the Florida Keys. Discover the Aviation Museum, see historic …

Celebrate 75 Years of Aviation at Marathon Airport! Read More »

Eighth Annual Stone Crab Claw Eating Contest
Eighth Annual Stone Crab Claw Eating Contest
Oct 20 all-day
Eighth Annual Stone Crab Claw Eating Contest
The much-anticipated opening of Florida’s stone crab season takes place Oct. 15 each year, and the season opening is followed by this tasty test of crab-consuming capacity. How fast can you crack and cleanly consume …

Eighth Annual Stone Crab Claw Eating Contest Read More »

21
Zombie Bike Ride 2:00 pm
Zombie Bike Ride @ Fort East Martello Museum
Oct 21 @ 2:00 pm – 3:00 pm
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 …

Zombie Bike Ride Read More »

22
Rams Head Productions presents: Michael Franti & Spearhead 6:00 pm
Rams Head Productions presents: Michael Franti & Spearhead
Oct 22 @ 6:00 pm – 10:00 pm
Michael Franti is a musician, humanitarian, and filmmaker who is recognized as a pioneering force in the music industry. Franti believes in using music as a vehicle for positive change and is revered for his …

Rams Head Productions presents: Michael Franti & Spearhead Read More »

23
24
Fantasy Fest Pet Masquerade
Fantasy Fest Pet Masquerade
Oct 24 all-day
Fantasy Fest Pet Masquerade
The eccentric competition is likely to include canine, feline and avian critters strutting their stuff on an oceanfront stage. “Party animals” can compete for costume prizes and glory. You will see a magic carousel of …

Fantasy Fest Pet Masquerade Read More »

25
36th Annual Headdress Ball
36th Annual Headdress Ball
Oct 25 all-day
36th Annual Headdress Ball
The Key West Business Guild presents this premier gay and lesbian event of the Fantasy Fest celebration, proudly opens the new Key West Amphitheater at the Truman Waterfront Park. Tom Luna returns as the outrageous …

36th Annual Headdress Ball Read More »

26
South Florida Symphony to Present 21st Season of Key West Concerts 9:49 am
South Florida Symphony to Present 21st Season of Key West Concerts
Oct 26 @ 9:49 am – 10:49 am
Audiences can experience a classic American opera and four Masterworks Series concerts with stellar soloists during the South Florida Symphony’s 21st season of performances in Key West, where the orchestra was launched.N
27
Bud Light Fantasy Fest Parade
Bud Light Fantasy Fest Parade
Oct 27 all-day
The madcap merriment of Fantasy Fest is to culminate during the Bud Light Fantasy Fest Parade through Key West’s historic downtown. Tens of thousands of spectators converge to cheer the parade’s elaborately costumed marching groups, …

Bud Light Fantasy Fest Parade Read More »

28
Third Annual Marathon’s Fall Harvest at Crane Point Museum
Third Annual Marathon’s Fall Harvest at Crane Point Museum
Oct 28 all-day
Third Annual Marathon’s Fall Harvest at Crane Point Museum
From 4-8 p.m., enjoy some old fashioned harvest-time fun to bring in the fall season! Hay rides, trail mazes, face painting, crafts for kids, cheeseburgers, chili dogs, apple cider, caramel apples, baked goods & live …

Third Annual Marathon’s Fall Harvest at Crane Point Museum Read More »

29
30
Women in Wine
Women in Wine
Oct 30 all-day
Tuesday, October 30th Women in Wine $20.00 for Tasters Guild members The Restaurant Store 1111 Eaton Street Tasters Guild Key West Wine Tasting at The Restaurant Store. Theme is “Women in Wine” in conjunction with …

Women in Wine Read More »

2019 Florida Keys Fishing Tournament Highlights 4:20 pm
2019 Florida Keys Fishing Tournament Highlights
Oct 30 @ 4:20 pm – 5:20 pm
2019 Florida Keys Fishing Tournament Highlights CalendarN
31
Key West Triathlon to Test Athletes’ Stamina and Speed Dec. 1 11:03 am
Key West Triathlon to Test Athletes’ Stamina and Speed Dec. 1
Oct 31 @ 11:03 am – 12:03 pm
A test of stamina, speed, endurance and discipline awaits athletes in the continental United States’ southernmost city during the Key West Triathlon, an annual challenge that draws competitors from around the U.S. and abroad.N