Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Reverend Raven and the Chain Smokin' Altar Boys
This Fringe Theater fundraiser is back by popular demand! These guys lit up the Armory last time they were in town (and sold out fast). Reverend Raven is as authentic as blues gets: original music in a classic blues style. You’ll want to get on that dance floor — we guarantee! This fundraiser includes open bar, buffet style food, incredible music, and all your Fringe friends!
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Best of the 72-Hour Film Challenge
A decade of bad decisions, no sleep, and accidental brilliance.
We're raiding the vault and pulling the most iconic, chaotic, and absolutely unhinged audience favorites from every year of the 72-Hour Film Challenge. These are the films people still talk about… sometimes proudly, sometimes with mild PTSD.
Expect geniuses running on no sleep, actors who definitely didn’t know what they signed up for, and plots held together with duct tape and desperation. Comedy, horror, heartfelt weirdness. You’ll get it all, whether you want it or not.
Fighting for Laughs, Too
Join us for Fighting For Laughs, Too — a night of powerhouse comedy featuring Sam Norton, Preston Gitlin, and headliner “The Reverend” Bob Levy, hosted by local veteran and comedian Petey Rancel. Building on last year’s sold-out success, this event delivers big laughs for an important cause.
All proceeds benefit AHERO, a 501(c)(3) organization dedicated to preventing Veteran and First Responder suicide through fellowship, outdoor adventures, and community support.
Your $50 general admission ticket directly helps fund AHERO trips here in Key West — creating healing connections and life-changing experiences for our nation’s heroes. Come laugh, support, and make a difference!
A Special Evening with David Lowery
Join us for a special evening with David Lowery, celebrated singer-songwriter and co-founder of the influential alt-rock bands Cracker and Camper Van Beethoven. Known for his sharp wit, distinctive voice, and genre-blending musical style, Lowery has written some of the most memorable rock tracks of the past three decades, including “Teen Angst (What the World Needs Now),” “Low,” “Euro-Trash Girl,” and “What the World Needs Now.”
Tropical Luncheon & Garden Party
Step into an afternoon of island elegance as the Key West Woman’s Club revives its charming 1950s Tropical Luncheon tradition. Enjoy conversations with bestselling author Lucy Burdette, a preview of KWAHS’s Smithsonian-affiliated exhibit FOOD: Celebrating Conch Cuisine, and insights from curator Dr. Cori Convertito. Chef Martha Hubbard adds culinary flair to this celebration of the flavors and stories that define the Keys.
A delightful blend of history, culture, and island charm — all in the heart of Old Town.
Super Football Party!
Huge 10’ big screen!
Each ticket includes: One dinner (one plate of BBQ Ribs or Chicken, with Roll, Bake Beans, Cole Slaw, and Dessert); Viewing the Game on the BIG Screen; Raffles; Squares; and Prizes! Full bar and drink specials available for purchase.
OPEN TO THE PUBLIC!
Tickets: $25 in advance, $30 at the door
SOMO's BIG GAME Tailgate & Watch Party
Celebrate Big Game Sunday at The Southernmost Beach Resort.
Enjoy an Unlimited Tailgate Buffet and Premium well/draft/wine OPEN BAR!!
Food only option available, too!
Total ticket price is all inclusive of tax, gratuity, and fees.
Seating is first come, first served.
BIG GAME Watch Party
Celebrate BIG GAME Sunday at The Marker Resort.
Enjoy a Tailgate Buffet and wine, draft beer, and premium well OPEN BAR.
Total ticket price is all inclusive of tax, gratuity, and fees.
Seating is first come, first served.
Mac's Place Big Game Party!
Doors open at 5:00 PM
Game starts at 6:30 PM
Location: Mac's Place, 1605 N. Roosevelt Blvd.
Tickets Include:
Two buffets open for the duration of the game
Open bar for the duration of the game, featuring:
Spirits: Concierge Vodka, Captain Morgan, Bacardi, Jim Beam, Jack Daniel’s, Tanqueray, Santoro Tequila
All draft and craft beers
Seltzers: High Noon, Surfside, Sun Cruiser, Good Boy Vodka Cocktails, & Sip Margs
Wines by the glass
Please note: Shots and shooters are not included.
Sondheim and Sullivan: An evening of the songs of Stephen Sondheim and Gilbert and Sullivan
Contralto Vira Slywotzky and pianist David Sytkowski return to Williams Hall! The acclaimed duo joins forces with special guest Phillip Cole White to bring you the songs of America’s beloved musical theater composer and lyricist Stephen Sondheim and W. S. Gilbert and Arthur Sullivan, the incomparable craftsmen behind Great Britain’s great operetta tradition. From “Dirty Old Man” to “Send in the Clowns,” experience the giggles, grit and glory of the finest musical storytellers in the English language.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Valentine's Day Sweetheart or Not Dance Party
Dress to Impress!
Dancing, DJ, Photo Booth, Desserts, and Refreshments
*For CFK Academy Students, Pre-approved Guests, & Monroe County School Students ONLY in grades 9-12
The Wearable Art Fashion Show
Looking for an afternoon of breathtaking art and bold fashion?
Don't miss the Key West Woman's Club's Wearable Art Fashion Show 2026.
Experience the thrill of the runway, where high fashion meets high stakes. Witness the debut of one-of-a-kind, handcrafted creations from our city's most innovative local designers. As each unique piece is revealed on the catwalk, it becomes available for live auction. This is your chance to acquire a signature work of wearable art directly from the designer and take home an unforgettable piece of fashion history.
Your attendance also supports "Creativity in Design" scholarships for Key West High School students.
SOMO Roots
Southernmost Beach Resort and Reggae Lou invite you to SoMo Roots, an afternoon of live music and island vibes taking place on Sunday, February 15, 2026. The festivities kick off at 1:00 PM.
The event features a dynamic lineup of live performances by Reggae Lou & The Kind Budz and Channel 3. While guests enjoy the beach party atmosphere, the event also serves as a fundraiser for the S.O.S. Foundation.
A FEAST OF WORDS AND FLAVORS WITH RUTH REICHL
Celebrate the magic of books, food, and community at the Friends of the Key West Library Gala—an unforgettable evening with a culinary legend.
Join us Monday, February 23, 2026, for the Friends of the Key West Library Fundraising Gala, featuring legendary food writer Ruth Reichl—author, critic, and culinary icon. Enjoy her exclusive interview, then mingle in the Palm Garden with delicious bites, tropical cocktails, and twinkling lights. Proceeds benefit the Key West Library—so come celebrate great books, great food, and our beloved little pink library!
Diamonds are a Girls Best Friend
On Saturday, March 7, the Key West Woman’s Club will host its annual fundraiser Diamonds are a Girls Best Friend!
Enjoy an open bar, fully catered dinner, lively music by Skipper Kripitz & friends, and dancing while you shine in your diamonds!
Jammy Buffet Live!
Join us for Jammy Buffet Live, featuring Jimmy Buffett's lead guitarist and accomplished songwriter, Peter Mayer.
Jimmy Buffett often spoke of “traveling the songlines,” a phrase borrowed from the Aboriginal tradition of mapping the land through music and story—paths that connect people, places, and moments across time. Jammy Buffet picks up that journey, where Buffett’s coastal storytelling meets the improvisational spirit of the jam band world.
Vintners Dinner
The iconic Vintners Dinner returns in 2026! “The ART of Tasting” is a chef-curated food and wine experience—an elegant evening of fine wines, delicious cuisine, and heartfelt community connection in beautiful, historic Williams Hall. Guests will enjoy a thoughtfully crafted multi-course tasting menu by Chefs John Corea and David Fuhrman, perfectly paired with exceptional wines presented by Pacific Southern Wine Company and Republic National Distributing Company. Erin McKenna hosts the evening of live music, Fine Wine & Cuisine, as we raise a glass to AH Monroe's four decades of compassion, innovation, and impact in the Keys.
Join us for an artful evening of wine, cuisine, and community connection!
The College of the Florida Keys 60th Anniversary Celebration
Toast to six decades of educational excellence at The College of the Florida Keys’ milestone 60th Anniversary Celebration, featuring fine dining, cocktails, historical exhibit, live music, and dancing in honor of the College's rich legacy and continued commitment to student success.
4th Annual FRLA Monroe R.O.S.E Awards
The ROSE (Recognition of Service Excellence) Awards recognizes Monroe County front line hospitality employees who demonstrate excellent customer service. These industry champions showcase the region’s commitment to creating an extraordinary visitor experience.
Sponsorship opportunities available.
Darcy Cooke Celebrates Great Women of Song: Timeless Voices, Unforgettable Music
Called a “swinging jazz singer…displaying versatility and a beautiful voice” by jazz journalist, Scott Yanow, Darcy’s “warm and inviting voice” exudes a depth of emotion that draws in and thrills her audiences. With a love of jazz and a background in theater, Darcy is a master of song interpretation and an engaging storyteller who effortlessly guides and charms audiences through an evening of pure entertainment.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Bougie Afternoon Tea Party
Mark your calendars for the second annual Key West Woman's Club Bougie Afternoon Tea Party on January 17th! This delightful event will benefit Take Stock In Children, with a $25,000 Monroe County scholarship to be awarded.
In addition to enjoying a lovely afternoon, there will be prizes for the most elegant attire, so bring your best bougie outfits, hats, shoes, and coats! Camille Russo Toler will provide charming musical entertainment while we sip tea and specialty cocktails. Don’t miss out—GET YOUR TICKETS NOW!!
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Swing Dance Night with the Paradise Swing Band
Step back in time for an unforgettable evening of music and dance! Williams Hall proudly presents Swing Dance Night featuring the high-energy sounds of The Paradise Swing Band, directed by Joe Dallas.
Joining him on stage will be Donna DeForrest, Mark Rose, Skipper Kripitz, and Tony Elitcher—keeping the dance floor alive with classic swing rhythms.
Ian Maksin: New Album Release Tour
Get immersed in the deep sounds of Ian Maksin's soulful one-man-cello orchestra, paired and blended with his vibrant voice, as he explores a collection of traditional songs from different corners of the world: Japan, Finland, Bosnia, Iran, Ukraine, Armenia, India, Kyrgyzstan, and Medieval France and Spain, woven together with original instrumental works.
His latest release Lullaby for the World is an amazing multilingual journey in search of peace, healing and empowerment through music. It reflects the path of a true musical globetrotter, shaped by countless journeys across continents as a touring artist, along with mountaineering, flying airplanes, practicing meditation, and collaborating with local musicians in search of the mystical thread that connects all cultures. This album invites listeners into a space of presence, clarity, and emotional restoration.
Christmas on the Keys! Piano Concert with James T. Slater!
Join us for Christmas on the Keys, a joyful, high-spirited piano concert featuring the incredible James T. Slater—two-time Grammy-nominated, piano-playing, bilingual singer-songwriter of Bolivian American descent. Signed to BMG Music Publishing/Nashville, James will be performing hits recorded by legends from Carrie Underwood, and Kenny Chesney, to Tim McGraw and Willie Nelson, to Keith Urban and Enrique Iglesias...as well as songs off his latest album, Shrimp Boat Sessions, recorded LIVE on the piano at Jimmy Buffett's Shrimp Boat Studio here in Key West.
Holiday Lights Trolley Tour
Join the Key West Parrot Head Club on a Holiday Lights Trolley Tour!
We will meet at Salute restaurant at 4:30pm to check in and get your wrist band. One drink (beer or wine) is included. Additional beverages can be purchased at happy hour prices. At 6:00 will walk over to the White St pier parking lot to board the trolley/train.
See all the best decorations on our holiday tour as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition!
The trolley leaves at 6:30pm sharp!
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Holiday Party with Key West JAZZ Allstars!
Come feel the magic of the best jazz musicians in Key West! The Key West Jazz Allstars will wow you. Enjoy music and dancing.
Featuring Terri White, Larry Baeder, Hal Howland, Bubba Lownotes, Tony Eitcher, and David Arndt.
Full Menu is available from Olive's Mediterranean Cafe.
Parking Lot is at 201 Truman, enter lot off of Emma St, about a block away.
1st Annual Christmas Tiki Olympics
Get ready to "Get Freaky at the Tiki" as Looe Key Tiki presents its 1st Annual Christmas Tiki Olympics on Saturday, December 13th, starting at Noon. This festive and quirky competition requires teams of 4 to 6 players to compete in 5 rounds of funny Christmas games, plus one player from each team will participate in a separate chicken wing eating contest.
Robert Albury “Key West’s King of Soul”
A homegrown Key West talent, Robert Albury, grew up on the corner of Amelia and Whitehead Streets in Bahama Village. Robert had nine brothers and they all sang. Young Robert Albury was most inspired by Louis Armstrong's performance in Key West. To Robert, the vocals of Soul music come from deep down within a special place in your heart. He says, “That’s what makes soul music so great.”
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
An Enchanted Evening in the Key West Gardens at Fort West Martello – Past, Present & Future
Join us for a very special evening amid a magical display of lights and tropical beauty as we honor 70 years of our beloved Key West Garden. Hear from some of our “keepers of the fort” as we celebrate the past, present and future in a visual display of lights, and garden history and as we share our exciting vision to continue to build on Key West Garden’s legacy.
Best of Key West Jazz Concert
Come feel the magic of the best jazz musicians in Key West! The Key West Jazz Allstars will wow you. Enjoy music and dancing. Full Menu is available from Olive's Mediterranean Cafe.
Parking Lot is at 201 Truman, enter lot off of Emma St, about a block away.
An Evening of Cinema and Celebration: A Fundraising Birthday Fête for Sir Billy Connolly
Join us for a sophisticated evening celebrating the birthday of the legendary actor and comedian, Sir Billy Connolly, with his wife, Lady Pamela Stephenson Connolly.
This exclusive gala is a fundraiser for the Key West International Dance Company (KWIDC). By securing your place, you are providing vital support for the artistic endeavors, community outreach, and educational programs that enrich the cultural fabric of Key West.
Your attendance helps ensure the future of professional dance in our vibrant community. Secure your tickets now for this memorable celebration of cinema, artistry, and philanthropy!
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Strange Journey: The Story of Rocky Horror
Join host Landon Bradbary as we celebrate the 50th anniversary of Rocky Horror. Strange Journey: The Story of Rocky Horror is a joyful and wild ride through the tale of the cultural juggernaut that is The Rocky Horror Picture Show. From its humble origins as a London fringe theater play, the documentary tracks its meteoric rise, fall and resurrection to become the biggest cult film of all time. With intimate access to its creator Richard O’Brien and other major players such as Tim Curry, Susan Sarandon and Lou Adler, the documentary explores what makes the play and film so singular: Its groundbreaking and transgressive themes, iconic performances and epic songs that took over popular culture.
Shorts & Sips
Presented in partnership with the Key West Film Festival
Join us for a cinematic evening that pairs global storytelling with great wine. The night kicks off with a selection of international documentary short films - including the latest film from from Emmy Winner Ondi Timoner - followed by a curated wine tasting featuring bold reds, crisp whites, and light bites. Stick around as we shift gears for a second block of shorts guaranteed to deliver big laughs—our comedy selections, hosted by Tom Dustin of Key West Comedy.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
PAUL MENTA BUTTERS YOU UP!
Prior to the Spotlight screening of Billy Corben's CANCELLED: THE PAULA DEEN STORY, let Paula's good friend, legendary chef and rum distiller Paul Menta, butter you up with dishes inspired by the cuisine of Paula Deen. Paul will be joined by Billy as they force you to unbuckle some of the notches on your belt buckle while you wash down the delicacies with a selection of Longoria Wines from the Santa Barbara Wine Country.
Your meal includes a ticket to the premiere of the film, playing immediately afterwards at Williams Hall and featuring a Q&A with Miami-based director Billy Corben (Cocaine Cowboys, Screwball, The U)
72 Hour Film Challenge!
Join us for the premiere screening of the 72 Hour Film Challenge—where creativity, caffeine, and chaos collide. Local filmmakers had just three days to write, shoot, and edit an original short film. Now it’s time to see their finished work on the big screen. Expect big laughs, wild twists, and plenty of Key West flair as we celebrate local talent and storytelling at its most daring.
Laugh Your Tails Off Comedy Night
Get ready to Laugh Your Tails Off with the Florida Keys SPCA at the Marathon Community Theatre on November 8th!
Join us for a fun evening of laughter featuring talented local comedians, all in support of the Florida Keys SPCA Marathon campus clinic fund! This fund helps us to provide affordable spay/neuter and preventative services to pet owners in our community.
Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.
Fall Showcase
Join us for the Drama Club’s 2025 Fall Showcase Fundraiser!
This year’s theme, Coming of Age, explores the moments that shape us — stories of growth, change, and finding our place in the world — all told through the voices and talents of high school students from our Key West community.
Vibrator Races for Charity!
The vibrator races at Mary Ellen's Bar in Key West are a unique and raucous charity event held every Thursday night. Far from a quiet affair, these races involve a lively atmosphere with loud music, confetti, and a "dong gong" to mark the excitement.
Swing Dance Night with the Paradise Swing Band
Step back in time for an unforgettable evening of music and dance! Williams Hall proudly presents Swing Dance Night featuring the high-energy sounds of The Paradise Swing Band, directed by Joe Dallas.
Joining him on stage will be Donna DeForrest, Mark Rose, Hal Howland, and Tony Elitcher—keeping the dance floor alive with classic swing rhythms.
Shoreline Sessions
Get ready for Shoreline Sessions presented by the Southernmost Beach Resort & Guesthouses in Key West! This epic two-day music event features Fortunate Youth and a fantastic lineup of artists.