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Events in the Florida Keys for September, 2025
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| September 19 to September 25,
in Key West |
Truman Waterfront Farmers Market - Every Thursday
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.
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| August 29 to September 01,
in Key West |
Just a Few Friends Key West
Come to Key West for Labor Day weekend to celebrate the 2nd Annual Just a Few Friends memorial, honoring our favorite son, the late Jimmy Buffett. Festivities kick off with an official pre-party meetup on Thursday, August 28. On Friday morning the City of Key West will proclaim “State of Florida Jimmy Buffett Day," followed by activities on and off the water, foodie events, and great times. Saturday features a run/walk, the Margarita Bar Crawl, along with tours, lectures, rum tastings, and music events across town. Sunday’s highlight is the epic Second Line Parade starting at 5 p.m. culminating in a free music festival at Truman Waterfront Park with local and national entertainment, food trucks and vendors. The events concludes with a Come Monday celebration with a variety of activities and entertainment options to suit every interest.
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| September 03 to September 07,
in Key West |
Womenfest Key West
The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling, sunset cruises to live entertainment, an art workshop and much more.
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| September 13,
in Islamorada |
Swim for Alligator Lighthouse
Join Islamorada's annual world-class, 8-mile open-water swim out to the iconic Alligator Reef Lighthouse and back. This unique and challenging experience can be conquered solo or on 2-, 3- or 4-person relay teams. Proceeds from the race go toward the effort to fully restore and re-light the 152-year old lighthouse.
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| September 19 to September 21,
in Big Pine |
Seacamp 60th Reunion
Join together with fell Seacamp alumni for a special 60th reunion event.
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| September 26 to September 28,
in Key Largo |
Take Stock in Children Backcountry Challenge
This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. Fishing is allowed around the clock from Friday night through Sunday afternoon. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.
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| September 26 to September 27,
in Islamorada |
Conch Scramble Charity Golf Tournament
The Conch Scramble is a charity golf tournament that uses boats instead of golf carts. Costumed teams boat to "holes" located at area marinas, bars and restaurants where players tee off from land to hit holes situated in the water. The legendary kick-off party - open to the public - takes place on Friday, Sept. 26 from 5 to 9 p.m. at SD Marine, mile marker 85.5 bayside, with the tournament on Saturday. Spectators can watch the wacky play from several favorite Islamorada watering holes on Saturday including Lorelei, Marker 88, and Oceanview Inn.
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