About our Keys Theaters and Events

Facts you might not know:

  • Fringe Theater is in it’s 17th season with their home at the Key West Armory. A small intimate theater experience and you never know what the sets will be. This theater cultivates new talent. All sponsors receive their logo on the 3’ x 8’ banners on the Armory building.
Good Night Oscar, February 2025. Photo by ROBERTA DePIERO
  • Red Barn Theatre is in its 46th year of productions. The oldest  and first professional theater in Key West. The theater is very intimate with only 88 seats in this historic old carriage building. Shel Silverstein, Tennessee Williams and Richard Wilbur all worked with the theater group intimately.
Watson and Sherlock February 2025 production. Photo by ROBERTA DePIERO
  • Waterfront Playhouse is in its 87th year. The biggest stage downtown, you will see some amazing sets. There are 150 seats in the historic ice block building. Did you know that the sets can cost them up to $30,000 per show?  They will be producing a stand alone program for Rocky Horror Picture Show in October as well as their regular season playbill.
Singing in the Rain production at Waterfront Playhouse where it actually rained on stage! January 2024. Photo by Roberta DePiero
  • Tennessee Williams Theatre: 45 years strong bringing Broadway shows and other small shows into town. It is our biggest theater at 508 seats. Black Box seats 150 audience members and the Cabaret seats 160 audience members.  Their black box and cabaret series are always a small and intimate audience experience. They’ve been bringing theater to the children of Monroe County as well. They have two separate programs.
Tennessee Williams Black Box set on the stage inside the theater.
Peking Acrobats, Mainstage Production 2025. Photo by Peter Arnow.
Tennessee Williams Cabaret Theatre
  • Marathon Community Theatre: Their 82nd season and they are the cultural center in the heart of the Florida Keys. The 135 seat theater has many productions Thursday through Saturdays.
Disenchanted – A New Musical Comedy at Marathon Community Theatre, April 2024. Photo (The Keys Weekly Newspapers shared via Marathon Community Theatre FB) Pictured: Kara Pascucci (Sleeping Beauty); Abbi Colella (Snow White)
  • Nutcracker Key West is produced by Tennessee Williams Theatre who brings this holiday ballet with a Key West twist to audiences every two years. The next production will be in December 2026. It’s not to be missed utilizing both Professional ballerinas and local children.
Nutcracker Key West production at Tennessee Williams Theatre, December 2022. Photo by Roberta DePiero
  • Impromptu Concerts: started with a dare to bring  small groups of classical musicians to a house and invite friends to listen over 54 years ago. They normally perform at St. Paul’s Church on Duval Street to a full house of over 350 for six concerts every January, February and March. Because of the church renovations in 2026, you can find their concerts at Tennessee Williams Theatre.
Impromptu Classical Concerts at St. Paul’s Church on Duval Street. 2025. Photo provided by Peter Arnow
  • Keys Choral Arts: This is our community chorus that has been around for many years but when the long time director died tragically in a car accident, the group reformed under this current name. Their program covers all three of their three concerts .  Two of their concerts are in December, just before the holidays and perform at St. Paul’s  Church on Duval Street.
  • Anne McKee Artist Fund: this program is for the annual art auction held at Studios of Key West. The Fund auctions off artwork from local artists, 50% of the proceeds goes back to the donating artist and the other 50% is used by the fund for their annual project based grants. Started in 1994,  artists helping artists has served to bring many emerging artists into their full fledged  careers.  Since its inception, the Fund has awarded almost $450,000 to over 400 visual artists, writers and performing artists who live in Monroe County.
Anne McKee Fine Art Auction February 2020. Photo by Carol Tedesco
  • Wesley House Family Services: This program will be featured at the Key West’s premiere fundraiser, The Wesley House Black Tie Benefit. This fundraiser helps service our at risk children here in Monroe County.   Supporting the program helps to underwrite theevent expenses so more money will go to the important work of the Wesley House.
  • Key West Film Festival: For 14 years bringing new movies to Key West many end up as Oscars nominees.
Key West Film Festival coming into it’s 14th Year in November 2025.

Williams Hall: is a community hub rooted in faith and culture, offering weekly dinners, concerts, classes, and theatrical events that bring people together. Located in the heart of Old Town, it serves as a gathering place for locals and visitors alike, with a focus on connection, creativity, and care. Programming includes culinary experiences, youth theater, senior wellness, and partnerships with many local nonprofits.

  • Key West Business Guild: They have two event programs coming up this fall, Womenfest Key West in September 2025 and the 42nd Annual Key West Headdress Ball during Fantasy Fest in October at the Key West Amphitheater.
41st Annual Key West Business Guild’s Headdress Ball Finalists, October 2024. Photo by Roberta DePiero
Key West Womenfest 2024 Words and Works Poetry Event. Photo by Peter Arnow