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DTSTART;VALUE=DATE:20261022
DTEND;VALUE=DATE:20261023
DTSTAMP:20260831T185914Z
CREATED:20230629T182247Z
LAST-MODIFIED:20260831T185914Z
UID:1720-1792627200-1792713599@www.historichideaways.com
SUMMARY:Key West Headdress Ball
DESCRIPTION:Key West Headdress Ball\nThursday\, October 22\, 2026 · Coffee Butler Amphitheater at Truman Waterfront Park\nDoors 6:30pm · Show 8:00pm\nThe Key West Business Guild presents the 43rd Anniversary Headdress Ball\, one of the most anticipated nights of Fantasy Fest. \nLegendary Key West entertainer Randy Roberts returns as host\, with music by WEOW’s RudeGirl. Twelve to fifteen contestants take the stage to reveal their headdress creations — judged from the shoulders up — competing for a $2\,500 grand prize. \nNew Award Categories\nThe Ball introduces six categories this year\, recognizing different kinds of artistic achievement: \n\nHead Above the Rest — $2\,500 · The night’s top honor\, for the creation that best combines artistic vision\, originality\, craftsmanship\, presentation\, and overall impact\nSpirit of Fantasy Fest — $1\,000 · For the creation that best captures the official Fantasy Fest theme\nPretenders in Paradise — $750 · A nod to the beloved former Fantasy Fest costume competition\, for the contestant whose costume and headdress read as one cohesive work\nGlow Getter — $500 · For the headdress that makes the biggest impact through creative illumination — LEDs\, neon\, or other lighting effects\nDream Team — $500 · For two or more artists who combine their talents into a single\, visually stunning presentation\nSize Doesn’t Matter — $500 · For the artist who makes a bold impression with a more compact design\n\nTotal prize purse: $6\,000 \nBetween competition rounds\, the evening features performances by some of Key West’s most celebrated local entertainers. Full bar service and specialty wines are available\, and food can be preordered and delivered right to your table. \nTickets\nPrices do not include fees \n\nPremium Table for 4 — $400 (includes your choice of a bottle of wine\, a bucket of beer\, or non-alcoholic beverage selections)\nVIP Table for 4 — $290\nReserved Chair Seating — $40\nGeneral Admission\, grass seating — $30\n\nThe Headdress Ball celebrates the artistic expression and inclusive spirit that have made Key West one of the world’s most distinctive destinations\, and this night one of Fantasy Fest’s signature events. \nThis event sells out every year — reserve your seats early. For tickets\, contestant information\, or to enter the competition\, visit gaykeywestfl.com/headdress-ball or call 305-294-4603. \nSchedule subject to change. Information courtesy of the Key West Business Guild — see their website for complete details.
URL:https://www.historichideaways.com/event/key-west-headdress-ball/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Arts,Festivals,Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270121
DTEND;VALUE=DATE:20270122
DTSTAMP:20260905T193128Z
CREATED:20260905T193128Z
LAST-MODIFIED:20260905T193128Z
UID:3312-1800489600-1800575999@www.historichideaways.com
SUMMARY:NoGravity Theatre
DESCRIPTION:Thursday\, January 21\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nOne of Italy’s most inventive performing arts companies makes a stop in Key West this January. NoGravity was founded in Rome in 2005 by artist Emiliano Pellisari\, and it has spent two decades building a form of theater that doesn’t fit neatly into any existing category — part dance\, part visual art\, part outright illusion. Bodies appear to float\, fall upward\, and dissolve into one another. The mechanics behind it are never explained and\, honestly\, are better left unexplained. \nThe company draws its imagery from the Italian Renaissance and Baroque\, translating the compositions of old master painting into moving bodies on a darkened stage. The result is dreamlike rather than technical — surreal tableaux that assemble\, hold for a beat\, and come apart. Since 2010 the dance cast has been led by Mariana Porceddu\, a graduate of the National Academy of Dance who became co-author of the company’s choreography in 2012. \nNoGravity performs annually in major Italian theaters and tours internationally with support from Italy’s Ministry of Cultural Heritage. This is the kind of production that rarely makes it this far south\, and it’s worth seeing on a proper stage rather than in a clip.
URL:https://www.historichideaways.com/event/nogravity-theatre/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270209
DTEND;VALUE=DATE:20270210
DTSTAMP:20260905T193730Z
CREATED:20260905T193730Z
LAST-MODIFIED:20260905T193730Z
UID:3318-1802131200-1802217599@www.historichideaways.com
SUMMARY:Afrique en Cirque
DESCRIPTION:Tuesday\, February 9\, 2027\nDoors 5:30pm\, Show 6:30pm · Tennessee Williams Theatre \nAfrique en Cirque comes to Key West as part of the Tennessee Williams Theatre’s new Family Fun Series\, a slate of shows programmed for audiences of all ages. It’s the signature production of Cirque Kalabanté\, the company founded by Guinean acrobat Yamoussa Bangoura\, and it draws directly on the daily life\, movement\, and music he grew up with in Guinea. \nThe show pairs high-level acrobatics with live music rather than a recorded score. Performers build human pyramids\, tumble\, and work the Cyr wheel while a band plays Afro-jazz built around percussion and the kora\, the twenty-one-string West African harp that gives the music its distinctive rippling sound. There’s no elaborate set to hide behind — the appeal is bodies\, rhythm\, and a company of young performers doing genuinely difficult things a few feet from the audience. \nIt’s a good fit for families\, and the earlier curtain reflects that: doors at 5:30 and a 6:30 start rather than the theatre’s usual 7:30. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/afrique-en-cirque/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270227
DTEND;VALUE=DATE:20270228
DTSTAMP:20260905T194427Z
CREATED:20260905T194427Z
LAST-MODIFIED:20260905T194427Z
UID:3321-1803686400-1803772799@www.historichideaways.com
SUMMARY:Ailey II
DESCRIPTION:Saturday\, February 27\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAiley II is the junior company of Alvin Ailey American Dance Theater\, and calling it a training ensemble undersells it considerably. Founded in 1974 as the Alvin Ailey Repertory Ensemble\, it exists to pair the strongest early-career dancers in the country with choreographers who are themselves still building their reputations. The result is a company with the technical polish of a major troupe and none of the caution — these are dancers with everything to prove\, performing work that hasn’t yet settled into repertory. \n \nPhoto by Nir Arieli and Danica Paulos\, courtesy of Ailey II\nSylvia Waters\, chosen by Alvin Ailey himself as founding artistic director\, led the company through its first thirty-eight seasons and built it into one of the most popular touring ensembles in American dance. Francesca Harper directs it today. Recent programs have included Rena Butler’s In Session and Judith Jamison’s Divining\, mixing new commissions with pieces drawn from the Ailey legacy. \nThe company tours widely but doesn’t often come this far down the Keys. Dance Magazine has called Ailey II second to none\, and The New York Times has described an evening with the company as its own distinct experience\, separate from the parent troupe. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/ailey-ii/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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DTSTART;VALUE=DATE:20270316
DTEND;VALUE=DATE:20270317
DTSTAMP:20260905T195643Z
CREATED:20260905T195022Z
LAST-MODIFIED:20260905T195643Z
UID:3324-1805155200-1805241599@www.historichideaways.com
SUMMARY:Celtic Angels Ireland
DESCRIPTION:Tuesday\, March 16\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nCeltic Angels Ireland arrives in Key West on the eve of St. Patrick’s Day with a full-scale production built around traditional and contemporary Irish music. The show is assembled by a creative team based in Ireland and cast with award-winning and World Champion singers\, dancers\, and musicians\, and it moves through more than thirty tunes over the course of the evening. \nThe vocal ensemble at the center of it — the Celtic Angels themselves — handle the close harmony work that gives the show its name. Around them\, the Celtic Knights Dancers bring the percussive step dancing the tradition is known for\, and the Trinity Ensemble plays everything live. No backing tracks\, which matters more in this repertoire than in most; the fiddle and whistle lines are half the point. \nThe program swings between registers the way Irish music tends to — laments and emigration songs on one side\, reels and set pieces on the other\, often within a few minutes of each other. It’s a good family show and an easy one to bring people to who don’t think they have an opinion about Irish music. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/3324/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270428
DTEND;VALUE=DATE:20270503
DTSTAMP:20260706T194000Z
CREATED:20230105T194740Z
LAST-MODIFIED:20260706T194000Z
UID:669-1808870400-1809302399@www.historichideaways.com
SUMMARY:Key West Songwriters Festival
DESCRIPTION:The Key West Songwriters Festival.\n4/28/27 – 5/2/27 \n\nThe Key West Songwriters Festival is the largest festival of its kind in the world\, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves\, Florida Georgia Line\, Jake Owen\, Michael Ray\, Randy Houser and Maren Morris. In its 27th year\, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.
URL:https://www.historichideaways.com/event/key-west-songwriters-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Concerts,Festivals
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