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X-WR-CALDESC:Events for Historic Hideaways
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DTSTART;TZID=America/New_York:20261208T080000
DTEND;TZID=America/New_York:20270102T170000
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CREATED:20260905T200354Z
LAST-MODIFIED:20260905T200354Z
UID:3332-1796716800-1798909200@www.historichideaways.com
SUMMARY:Shooting Star
DESCRIPTION:December 8\, 2026 – January 2\, 2027 · Shows at 7:00pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn opens its holiday slot with Shooting Star\, a two-hander by Steven Dietz\, one of the most widely produced playwrights working in American theater. The setup is simple enough to describe in a sentence: two people who were together in college get snowed in overnight at a middling airport in the middle of the country and find themselves face to face for the first time in years. \nWhat follows is the whole play — no scene changes\, no third character\, nowhere for either of them to go. They talk. They avoid talking. They circle the years between then and now\, the versions of themselves the other still half-expects\, and the question of what they actually meant to each other. Dietz keeps it funny throughout\, and the comedy does most of the heavy lifting until it quietly stops being only funny. \nThe Red Barn production stars Dave Bootle and Lauren Thompson\, with Joy Hawkins directing. It’s ideal material for a house this size — the Red Barn seats fewer than a hundred\, and a play built entirely on two people reading each other across a row of airport chairs lands very differently at close range. Several extra Monday performances have been added over the holidays. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/shooting-star/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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DTSTART;TZID=America/New_York:20270107T080000
DTEND;TZID=America/New_York:20270109T170000
DTSTAMP:20260905T202454Z
CREATED:20260905T202454Z
LAST-MODIFIED:20260905T202454Z
UID:3352-1799308800-1799514000@www.historichideaways.com
SUMMARY:Blanche and Beyond
DESCRIPTION:January 7 – 9\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Spotlight Series continues with Blanche and Beyond\, Steve Lawson’s one-man play assembled from Tennessee Williams’s own letters. It’s the sequel to Lawson’s A Distant Country Called Youth\, which drew on the early correspondence; this one covers 1945 through 1957\, the stretch that produced A Streetcar Named Desire\, Summer and Smoke\, The Rose Tattoo\, and Cat on a Hot Tin Roof. \n \nThe letters are by turns funny\, obscene\, and unguarded\, and they catch Williams in the middle of something he never quite adjusted to — going from unknown to internationally famous in the space of a few years. He writes about Brando\, Jessica Tandy\, Elia Kazan\, David O. Selznick\, Laurence Olivier\, and Vivien Leigh\, and about the plays still forming in his head. \nWilliams was living in Key West through most of the years these letters cover. He bought the Duncan Street house in the late 1940s and kept it until his death. \nBlanche and Beyond opened the Tennessee Williams New Orleans Literary Festival in 2006\, in a production directed by Lawson and performed by Richard Thomas. Three performances only in Key West. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/blanche-and-beyond/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270115
DTEND;VALUE=DATE:20270118
DTSTAMP:20260831T184853Z
CREATED:20230105T153545Z
LAST-MODIFIED:20260831T184853Z
UID:592-1799971200-1800230399@www.historichideaways.com
SUMMARY:29th Annual Key West Half Marathon & Runfest
DESCRIPTION:29th Annual Key West Half Marathon & Runfest®\nJanuary 13–18\, 2027 · Race weekend January 15–17 \nKey West offers a multitude of exciting experiences\, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure\, making it an unforgettable destination. And let’s not forget the intriguing fact of having 400 bars on an island that’s only 2 x 4 miles. Set aside some extra time to explore all that Key West has to offer. \nSchedule of Events\nWednesday\, January 13\nVolunteer Check-In & Party · 11am–1:30pm · Sailfish Bar at Half Shell Raw Bar\, 231 Margaret St \nThursday\, January 14\nRunner’s Meet & Greet with drink specials · 4:30–6pm · Sailfish Bar\, Half Shell Raw Bar \nFriday\, January 15\nRunner’s Expo & Packet Pick-Up · 2–7pm · Outside Half Shell Raw Bar\nLate bib pick-up (bibs only) · 7:15–10pm · Fit2Run\, 211 Duval St\nAll-day drink specials at Half Shell Raw Bar \nSaturday\, January 16 — 5K & 10K\nBag check · 6–6:45am · In front of Salute! On the Beach\, 1000 Atlantic Blvd\n5K start/finish · 7am · Higgs Beach\n10K start/finish · 8am · Higgs Beach\nConcert & Awards Party with Homebred Band featuring Dave Richards · 8–11am · Outside Salute! On the Beach\nOverall winners announced · 9:30am\nRunner’s Expo & Packet Pick-Up · 1–6pm · Outside Half Shell Raw Bar\nPresentation by Dr. Kellee Reed · 3:30pm\nLate bib pick-up (bibs only) · 7–10pm · Fit2Run\, 211 Duval St\nEarly breakfast and all-day food/drink specials at Salute! and Half Shell \nSunday\, January 17 — Half Marathon & 8K\nBag check · 6–6:45am · Lot by the finish line at Waterfront Brewery\nHalf Marathon start · 7am · Caroline St & Trumbo Rd\n8K start · 7:30am · Same start line; finish behind Waterfront Brewery\nConcert & Awards Party with The Cayo Ritmo Big Band · 8:30am–12:30pm · Outside Half Shell Raw Bar\n8K awards 9:30am · Half Marathon awards 10:30am\nPapa’s Pilar Rum Stroll · 1–5pm · Nine stops from the distillery on Simonton to Southernmost Beach Cafe\nBeach ‘N Beer Mile (untimed; four loops\, four beers) · 3pm · Southernmost Beach Cafe\, 1405 Duval St\nCool Down Pool Party\, free entry · 4–6pm · Blue Flamingo Resort\, 3820 N Roosevelt Blvd\nKey West Farewell Party · 4–6pm · Salty Oyster at the Perry Hotel\, 7001 Shrimp Rd\nAll-day Bloody Mary\, mimosa\, and vodka specials at Half Shell \nMonday\, January 18\nMarathon Farewell Party & Happy Hour · 4–6pm · Blu Bistro at Skipjack Resort & Marina\, 19 Sombrero Blvd\, Marathon \nSchedule subject to change. Information courtesy of the event organizers — see their website for registration\, updates\, and complete details.
URL:https://www.historichideaways.com/event/annual-key-west-half-marathon-5k/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270118
DTEND;VALUE=DATE:20270119
DTSTAMP:20260905T192050Z
CREATED:20260905T192050Z
LAST-MODIFIED:20260905T192050Z
UID:3309-1800230400-1800316799@www.historichideaways.com
SUMMARY:The Doo Wop Project
DESCRIPTION:Monday\, January 18\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAmerica’s premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo Wop Project takes today’s biggest hits and “doowop-ifies” them — reimagining contemporary songs as though they’d been written and recorded in 1958. Familiar melodies arrive wrapped in tight harmony\, walking bass lines\, and finger-snap rhythm\, and the effect is genuinely surprising the first time you hear a modern radio staple come at you in a completely different decade. It’s the reason audiences around the country leave these shows talking\, and the reason the group has built a following well beyond the generation that grew up with the original records. \nAn evening at the Tennessee Williams Theatre is one of the more comfortable nights out in Key West — a proper 480-seat house on the College of the Florida Keys campus\, with easy free parking\, which is not something you can say about most venues on this island. Subscription packages covering the full 2027 season are available at a 15% savings if you’re planning to catch more than one show. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-doo-wop-project/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Theater
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DTSTART;TZID=America/New_York:20270119T080000
DTEND;TZID=America/New_York:20270220T170000
DTSTAMP:20260905T200725Z
CREATED:20260905T200725Z
LAST-MODIFIED:20260905T200725Z
UID:3336-1800345600-1803142800@www.historichideaways.com
SUMMARY:Dracula: A Comedy of Terrors
DESCRIPTION:January 19 – February 20\, 2027 · Tuesdays–Saturdays at 7:30pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn follows its holiday show with Dracula: A Comedy of Terrors\, the Gordon Greenberg and Steve Rosen send-up that became an off-Broadway hit and has been working its way through regional theaters ever since. The premise is the Bram Stoker story you already know\, played entirely for laughs — a high-camp spoof that borrows its sensibility about equally from Mel Brooks and Monty Python and never slows down long enough for anyone to take it seriously. \nThe whole thing runs on a small cast covering a great many characters\, with gender-bent casting\, quick changes\, and a fair amount of deliberate chaos. Jokes land at a clip\, the physical comedy is broad on purpose\, and the script is happy to break its own logic if there’s a bigger laugh available. If you’ve seen the Red Barn take on this kind of material before\, you know they commit. \nThe Key West production stars Jody Orrigo\, Susannah Wells\, Erin McKenna\, Phillip Cole White\, and Dominic Paolillo\, directed by Mimi McDonald. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/dracula-a-comedy-of-terrors/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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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:20270126
DTEND;VALUE=DATE:20270131
DTSTAMP:20260831T193706Z
CREATED:20230105T192332Z
LAST-MODIFIED:20260831T193706Z
UID:638-1800921600-1801353599@www.historichideaways.com
SUMMARY:Annual Mile 0 Fest Key West
DESCRIPTION:Mile 0 Fest Key West\nJanuary 26–30\, 2027 · Truman Waterfront Amphitheater and venues across the island\n10th Anniversary — Red Dirt\, Americana & Texas Country\nNamed the #1 music festival of 2025 by USA Today\, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee Butler Amphitheater at Truman Waterfront\, while daytime sets spill out across more than ten stages — beaches\, pools\, piers\, bars\, boats\, the historic Key West Theater\, and a few pop-up sets that aren’t on any schedule. Music runs roughly 11am to 11pm daily\, with late-night shows after the amphitheater sets. \n2027 marks the festival’s 10th anniversary\, and organizers are calling it their biggest year yet. New for the anniversary: The Reach Key West joins as a daily venue\, the amphitheater gets upgraded premium viewing and guest amenities\, and more guesthouse buyouts turn additional properties into festival lodging. \n2027 Lineup\nHeadliners include Cross Canadian Ragweed\, Ryan Bingham\, Old Crow Medicine Show\, Wyatt Flores\, and Kaitlin Butts. \nAlso on the bill: Wade Bowen\, 49 Winchester\, William Clark Green\, Stoney LaRue\, American Aquarium\, Tanner Usrey\, Cody Canada and the Departed\, Silverada\, Corb Lund\, Jason Scott & The High Heat\, Taylor Hunnicutt\, Kevin Fowler\, Roger Creager\, Micky & the Motorcars\, The Creekers\, The Jack Wharff Band\, Nicholas Jamerson\, Pony Bradshaw\, The Droptines\, Bri Bagwell\, Courtney Patton\, Adam Hood\, Jamie Lin Wilson\, and Shelby Stone\, among more than fifty artists. \nPasses & Packages\nFull experience packages bundle lodging with festival access and include perks you can’t buy separately — a Tuesday kickoff happy hour\, a private “Songwriter Spotlight” theater show\, and the “Sessions at Sea” live music sail. \n\nPlatinum Premier Package — from $3\,326 per person (based on two) · Sold out\nGold Premier Package — from $2\,683 per person\nPirate Package — from $2\,033 per person\nBeach Bum Package — from $1\,856 per person\nWeekender Package — from $1\,233 per person (three nights\, Thursday–Sunday)\n\nFestival-only passes are also available: \n\nPlatinum VIP Pass — $1\,646 · Sold out\nGold VIP Pass — $1\,175\nBeach Bum Pass — $587\n\nA $50 per-order discount is available through GOVX for military\, first responders\, and law enforcement. Single-day passes are expected to be released closer to the festival. \nGood to Know\nParking near the amphitheater is essentially nonexistent — walk\, bike\, or take a taxi or rideshare. All events run rain or shine. The festival app carries the full daily schedule\, typically posted about 30 days out\, along with set times and pop-up announcements. Mile 0 Fest gives back\, too. In 2026 fans raised more than $55\,000 for the Red Dirt Relief Fund\, Key West Wildlife Center\, and Key West Civic Association\, with signed guitars auctioned nightly. \nSchedule and lineup subject to change. Information courtesy of Mile 0 Fest — see mile0fest.com for packages\, passes\, and complete details. \n\n\nBOOK YOUR VACATION RENTAL FOR THE Mile 0 Fest \n\n\nDon’t wait to book your Key West vacation rental if you’re planning on attending the Mile 0 Fest. Choose from our selection of luxury homes\, vacation rentals with a pool\, pet friendly rentals\, condos or townhomes. \nBrowse Vacation Rentals>>>
URL:https://www.historichideaways.com/event/annual-mile-0-fest-key-west/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Festivals,Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270127
DTEND;VALUE=DATE:20270201
DTSTAMP:20260831T184548Z
CREATED:20230105T192722Z
LAST-MODIFIED:20260831T184548Z
UID:642-1801008000-1801439999@www.historichideaways.com
SUMMARY:Key West Food and Wine Festival
DESCRIPTION:2027 Key West Food and Wine Festival\nJanuary 27–31\, 2027 \n5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs \nWelcome to Key West Food & Wine Festival 2027\nA curated journey through the culinary heritage of five continents\, featuring world-renowned chefs\, their signature dishes\, and the legendary wines that define their regions. \nThis journey spans five continents with iconic wines\, each telling a story of terroir\, history\, and culture: \n\nAfrica: a smoky Pinotage\nEurope: a structured Bordeaux\nSouth America: a robust Malbec from Mendoza\nOceania: a vibrant Marlborough Sauvignon Blanc\nNorth America: a cool-climate Pinot Noir from Oregon\n\nThe Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie\, Key West is the place to be in January. With many unique events\, held at spectacular island locations\, this is an opportunity to enjoy a wide variety of wines and cuisine\, with waterfront tastings\, wine/food pairings\, and local events around Key West. \nAt a Glance\nWednesday\, January 27 — Welcome to the Festival\nVIP Welcome Party · 5–7pm · Realty One Group Destination\, 1075 Duval St \nThursday\, January 28 — Around the World\nThe Wine Game\, a tasting challenge · 11am–1pm · Key West Cooking Show\, 291 Front St\nWelcome to Oceania: Island Flavors Dinner with Chef Dave Fuhrman · 6–9pm · Audubon House & Tropical Garden\, 205 Whitehead St \nFriday\, January 29 — Europe & North America\nHidden Gems & Golden Sips · 1:30–4pm · Trolley departs Gardens Hotel\, 526 Angela St\nFive Continents Grand Tasting · 6–8pm · Key West Aquarium\, 1 Whitehead St\nAn Exclusive Celebration of American Spirit · 7–10pm · Truman Little White House\, 111 Front St \nSaturday\, January 30 — Key West\, North America & South Africa\nCooking with Love: The Saturday Kitchen Party · 8:45–10am · 1215 Petronia St\n“A Dream Come True” · 12–2pm · Venue TBA\nWelcome to South Africa: Lost Kitchen Supper Club · 6–9pm · Trolley pick-up 5:45pm \nSunday\, January 31 — Europe\nPranzo on the Amalfi Coast · 12–2pm · Conchiglia Key West\, 816 Duval St \nSchedule subject to change. Information courtesy of the Key West Food & Wine Festival — see their website for tickets\, updates\, and complete details.
URL:https://www.historichideaways.com/event/key-west-food-and-wine-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270128T080000
DTEND;TZID=America/New_York:20270206T170000
DTSTAMP:20260905T202701Z
CREATED:20260905T202701Z
LAST-MODIFIED:20260905T202701Z
UID:3355-1801123200-1801933200@www.historichideaways.com
SUMMARY:Unnecessary Farce
DESCRIPTION:January 28 – February 6\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage returns to Paul Slade Smith\, whose The Angel Next Door played there previously\, with Unnecessary Farce. Two cops have set up a sting in a cheap motel\, hoping to catch the mayor taking a bribe. There are two adjoining rooms\, a video camera pointed at the wrong one\, an accountant\, three crooks\, a Scottish hit man\, and eight doors. \nSmith’s play premiered in 2006 and has since become one of the most frequently produced comedies in American regional theater\, largely on the strength of its construction — the plot is engineered so that every escalation follows logically from the last\, however absurd things get. \nReviewers have called it the funniest thing they’d seen in years\, and credited Smith with making the in-one-door\, out-the-other machinery feel new again. It runs about two hours. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/unnecessary-farce/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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