Facts you might not know:
- Fringe Theater is in it’s 18th season with their home at the Key West Armory. A small intimate black box theater experience and you never know what the set-up will be. This theater cultivates new talent. All sponsors receive their logo on the 3’ x 8’ banners on the Armory building.
- Red Barn Theatre is in its 47th 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.
- Waterfront Playhouse Celebrating its 89th season and located on historic Mallory Square, the Waterfront Playhouse is Florida’s oldest professional theatre. Renowned for outstanding production values, exceptional performances, and consistently high standards, it has become one of Key West’s most cherished cultural treasures. The biggest stage downtown, you will see some amazing sets. There are 150 seats in the historic ice block building. They will be producing a stand alone program for “Hedwig and the Angry Inch” in October as well as their regular season playbill.
- Tennessee Williams Theatre: 46 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.
- Marathon Community Theatre: is celebrating its 83rd season as the cultural heart of the Florida Keys. For the past 30 years, MCT has called its current home a welcoming gathering place for the community. The 144-seat theatre presents a vibrant season of live performances Thursday through Sunday, showcasing Broadway favorites, contemporary works, comedies, dramas, musicals, and locally inspired productions.
- 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.
- Impromptu Concerts: started with a dare to bring small groups of classical musicians to a house and invite friends to listen over 55 years ago. You can find their concerts on Sunday afternoons at Tennessee Williams Theatre.
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 followed by a spring concert and perform at various churches in Key West.
- 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.
- Wesley House Family Services: A Century of Compassion! 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 15 years bringing new movies to Key West many end up as Oscars nominees.
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 2026 and the 43rd Annual Key West Headdress Ball during Fantasy Fest in October at the Key West Amphitheater.
