|There are so many Florida Keys Adventure Activities to enjoy in September through November. The fishing is spectacular and the concert halls are filled with musical events, “Keys” style. Florida Keys fishing tournaments abound and fun festival events are in full swing for the Summer from Key Largo – Duck Key – Marathon – Key West!
September 3 – 8
Womenfest Key West
Womenfest offers a wide range of activities guaranteed to appeal to a broad range of interests. Golfing with palm trees and iguanas, clothing-optional pool parties, a sizzling dance club scene, and women-only water excursions that range from jet skis to dolphin watching all promise to pique the interest of the more adventurous while film, live music, and special comedy shows offer the opportunity to enjoy paradise at a slower pace. All of this on a tropical island that is close to perfect and far from normal!
The Florida Keys
September 19 – 22
41st Annual Phil Peterson’s Key West Poker Run
It’s an All-American event as motorcycle enthusiasts from around the U.S. travel the Keys’ scenic Overseas Highway – designated Florida’s only All-American Road – from mainland Florida to Key West to raise money for charity. Winner takes all, and can win a new Harley-Davidson Motorcycle or cash. Stops are arranged throughout the Keys with a final celebration in Key West. New this year: Poker Run stops are to be open for riders starting Thursday, Sept. 19 through Sunday, Sept. 22; more Keys-wide events to be planned for the entire week; cash prize to the person wearing the oldest official Phil Peterson’s Poker Run T-shirt.
September 19 – 22
Marathon International Bonefish Tournament
For more than 50 years, this challenge awards individual and team champions scoring the largest bonefish and permit, the top anglers in fly and grand slam divisions (for the top spin or fly angler who releases the largest bonefish, permit and tarpon “slam”), as well as the tongue-in-cheek “wet pants” champion titles for anglers wading from shore.
the Florida Keys
September 25 – 29
Florida Keys Birding & Wildlife Festival
The peak of the fall birding season, this event includes an opening reception, dinner, presentations, Keys-wide field trips focusing on education and conservation as they relate to Keys birds and wildlife, nature photography, hikes, kayak excursions and a family-fun environmental fair.
NEW DATE: Conch Scramble On-the-Water Golf Tournament
Join an on-the-water wacky charity golf tournament that brings together four-person teams to enjoy a game of nine holes by boat, to “drive” biodegradable golf balls toward floating greens – without any sand traps. A kick-off party and team registration is to be held Friday, Sept. 27. A live or silent auction as well as a 50/50 cash raffle also are planned. Teams tee off Saturday with shotgun start at 9 a.m.
October 1 – 3Women’s Fall Fly Classic
The Women’s Fly Series includes both spring and fall angling challenges. Tournament rules mandate that the angler/guide team with the most species released earns the grand champion award. Species targeted are bonefish, redfish, snook and tarpon
October 10 – 13
SoMo Marathon & Half Marathon
Presented by Pat Croce’s Rum Barrel, 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 miles of ocean and gulf views, as well as iconic Key West landmarks. A full weekend of events include the race and a Sunday Paddle Board race for the Special Olympics of Monroe County
October 13 – 16
Bonefishing World Championship/ Islamorada All-Tackle BonefishI
Dubbed the “Fall All-Tackle,” the three-day challenge attracts energized newcomers to face seasoned veterans, in a competitive format since 1970. One angler per boat pairs with a licensed captain to vie for division winners’ trophies. Field is limited to 25 participants.
October 18 – 19
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.
October 18 – 27
34th Annual Fantasy Fest
This outrageous 10-day costuming and masking celebration, themed “Superheroes, Villains … and Beyond!” features flamboyant costume competitions including one for pets, promenades, street fairs and a grand parade that stars marching groups, island bands and lavish floats. More than 40 masquerade contests, themed parties, parades and other spectacles are to challenge the creativity of mask and costume designers.
Third Annual Stone Crab 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 25 stone crab claws? Test your munching mettle at this zany contest. Register by 12 p.m., contest starts at 1 p.m., entry fee is $25 per contestant, and individuals must be at least 18 years old to enter. Interested eaters are encouraged to register early.
October 31 – November 1
The Rocky Horror Show
Let’s Do The Time Warp Again … at The Murray E. Nelson Government and Cultural Center! Located at mile marker 102 bayside. Ginsberg Productions is a non-profit, community based, theatrical organization.
November 3 – 10
Key West World Championship RaceHigh-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 31st annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power.
November 8 – 9Fifth Annual Key Largo Bridge Run
The out-and-back foot race crosses the 65-foot-high, 1.25-mile-long Jewfish Creek Bridge and the southern portion of the 18-Mile Stretch, a segment of U.S. Highway 1 between Florida City and Key Largo that was recently completed after $330 million in improvements. The 10k event in addition to a half marathon and 5k run/walk is open to all ages, and is held in conjunction with a health & fitness expo each year.
November 13 – 17Second Annual Key West Film Festival
Showcasing films that exhibit excellence in storytelling, the festival’s lineup is to feature screenings and special events hosted at landmark venues throughout Key West, including the Tropic Cinema and San Carlos Institute. The four-day program is to include several films from multiple genres and categories as well as social events with filmmakers, actors.
November 21 – 24
Second Annual Chalkfest
Artists from across Florida will take their craft to the streets of Key West. Presented by the Key West Art In Public Places Board. Each day from 10 a.m. to 6 p.m. both local and visiting artists will use the promenade alongside the seawall at the Truman Waterfront as their canvas for intricate and colorful chalk art creations. A Key West pet friendly eventand film lovers.
November 21Morada Way Arts & Cultural District presents: Third Thursday Art Walk
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 – formerly named Industrial Road – as well as “culinary art” and live music from 6-9 p.m. In addition to individual artists, participating galleries include the Redbone Gallery, Gallery Morada, Pasta Pantaleo Signature Gallery and Bluewater Potters. Free admission. Art Walk is held the third Thursday of each month.
November 27 – December 31Key West “Bight’ Before Christmas” Holiday Celebration
Live holiday music, games for the kids, holiday cheer and a chance for photos with Santa highlight this event along the historic harbor walk linking colorful seaport restaurants, bars and businesses at the Key West Bight. Created as a gift to the community, the gala is produced by the Key West Bight Preservation Association and tenants of the Key West Bight.