September in Key West Offers Events to Roar About
Ahhhh, September … historically the month we celebrate the last holiday of the summer. In the United States we call it Labor Day, in Australia Father’s Day tops off the ninth month, it’s Brazil’s month to mark Independence Day, and in Germany there’s Oktoberfest.
September and December always begin on the same day of the week, since 91 days separate the months — and no other month ends on the same day of the week as September in any given year!
During September here in Key West, we just celebrated one of the biggest Womenfest events in the festival’s 30-year history (Womenfest, by the way, always starts on the first Tuesday of September).
Poker Run bikers have come and gone, and a few of our restaurants and shops take holidays this month.
The weather begins to cool down and we get into full swing preparing for the outrageous annual Fantasy Fest masking and costuming festival.
In a couple of weeks, our island will welcome bears, cubs, otters, wolves and a dusting of Goldilocks and chasers. Key West’s annual Bear Fest runs Oct. 4-7 with a full schedule of events throughout the weekend.
The animal antics begin with a noon pool party at the Island House resort. Local restaurants Square One and Antonia’s have special menus for this fun group that enjoys food and drink. The Brazilian churrascaria Braza Lena will welcome the exuberant appetites of the bears with the annual Saturday night limitless Carnivale for Carnivores featuring 16 cuts of meat.

Bears and their fellow party animals are expected to prowl into town for some pre-hibernation enjoyment. (Photo courtesy of Key West Bear Fest)
Be part of the pack as these “party animals” frolic across Key West joined by celebrity comedian host Paul J. Williams, acclaimed for his work with RSVP Vacations cruises and appearances on Logo television.
Williams will kick off the weekend at the Island House’s pool party, appear at events throughout the weekend and star in a one-man comedy show on Friday night at Bourbon St. Pub. Known as a “creative teenager” in the band, choir, and drama club, Williams has honed a sidesplitting sense of humor blended with lightning-fast wit.
Changing the pace a bit, our art scene cranks up with the monthly Walk on White Street held on the third Thursday evening of each month. Galleries are open for tours with refreshments and the local cafés offer samples of their specialties.
The first Friday evening of each month brings an Art Stroll to Upper Duval Street. The lively stroll includes gallery and studio tours featuring local artists, and restaurants and bars offering live entertainment and food and beverage specials.

Art like Kim and Ian Workman's beautiful piece graces the Key West International Airport terminal as part of an Arts Council initiative.
The Florida Keys Council of the Arts is a great resource to help you connect with our local artists, galleries, and special events — both in Key West and throughout the Florida Keys. The organization also promotes and supports an Art in Public Places program and assists our visual and performing artists and students.
Hope to see you at one of our September events, or sometime soon here on the island. After all, no matter what the month, there’s no place like Key West!


