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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2022

  • February 05 - Jan 07, 2023 Key West
  • Market on the Green
  • Website
  • Held the first Saturday of every month from 10 a.m.- 2 p.m., visitors and residents are invited to browse and shop amazing local artisans. The monthly market is located at the Sunset Green Event Lawn, at Key West’s 24 North Hotel.

  • March 31 - Dec 11, 2022 Key West
  • Key West Bicentennial Exhibit at The Custom House Museum
  • Website
  • Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.

  • September 25 - Nov 30, 2022 Key West
  • Scarecrows in the Forest Art Exhibit and Contest
  • Website
  • The Key West Tropical Forest & Botanical Garden is showcasing local artists’, community members’ and local students’ unique versions of the fall season’s ‘Scarecrows in the Tropical Forest.’ The scarecrows, made from natural and recycled materials, may be discovered throughout the 15-acre garden. The exhibit, open 10 a.m. to 4 p.m. daily, will be a lesson in recycling, art talent and a contest with cash prizes for the entries. The Garden is located at 5210 College Road.

  • November 23 - Dec 31, 2022 Key West
  • 2022 Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.

  • November 29 - 30, 2022 Key West
  • The Studios of Key West: Southern Skies Stargazing with Larry Halstead
  • Website
  • Artist and astronomy buff Larry Halstead takes participants to the cosmos and back. Meet in the theater for a presentation on the first night, then use a powerful telescope on the roof for direct observation the next night. From 7 to 9 p.m. both nights at The Studios of Key West, 533 Eaton Street, Key West. $55 per person.

  • December 01 - Jan 01, 2023 Key West
  • Key West Holiday Fest
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

  • December 01 - 04, 2022 Key West
  • COAST is CLEAR Music and Arts Festival
  • Website
  • Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main events are concerts at the festival grounds Saturday and Sunday. Two-day General Admission, VIP tickets and detailed information is available online. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.

  • December 01 Key West
  • World AIDS Day Processional and Service at Key West AIDS Memorial
  • Website
  • All are welcome to gather to celebrate the lives of friends and loved ones taken from us far too soon and honor those that we lost in 2022. There will be a processional starting at 4:30 p.m. from Key West City Hall, located at 1300 White Street, ending at the Key West AIDS Memorial. The names currently inscribed will be read by those walking and by those gathered at the memorial. The actual ceremony will take place from 6 to 7 p.m. at the memorial located at the Edward B. Knight pier, 1707 White Street. The names of those lost in 2022 will be unveiled. Participating in the processional this year will be the Key West Mile Markers SMART Ride team with the Riderless Bike in recognition of those lost to HIV/AIDS.

  • December 01 - 03, 2022 Key West
  • Tropic Cinema: Neil Young
  • Website
  • "Neil Young: Harvest Time" is a fan piece that has never before been seen. Performance and rehearsal content is intertwined into creative storytelling and includes most of the tracks from the iconic 1972 album Harvest. Created in 1971, this docu-film takes us on a journey to Neil Young’s farm in Northern California for the ‘Harvest Barn’ sessions, to London for an iconic performance with the London Symphony Orchestra and to Nashville where Young worked on various tracks of this signature album. Screenings at 7:30 p.m. on Dec. 1 and Dec. 3. 416 Eaton Street.

  • December 02 - 03, 2022 Key West
  • Revival Roadshow at Sunset Pier
  • Website
  • The Revival is a gathering of Nashville’s biggest hit writers sharing their songs, considered some of the best music in Nashville. In 2022 the Revival took the pew on the road with some of Nashville's greatest songwriters. The tour ends in Key West with two days of live music at Ocean Key Resort's Sunset Pier, Dec 2-3, with performances of 31 Number 1 hit songs by the songwriters that created them. Tickets available online. Single day pass $40; weekend pass $66.50.

  • December 02 Key West
  • Holiday Village & BeLighted Bike Ride
  • Website
  • The Wesley House Family Services’ Holiday Village & BeLighted Bike Ride is a great family-friendly event to help kick off the holiday season. The Holiday Village from 4-8 p.m. features community and vendor booths, food trucks, a best bike contest at 7 p.m. and photos with Santa. The bike ride leaves at 8 p.m. Admission $15 adults, $10 children, kids 4 and under free. Find tickets, information and bike contest registration online.

  • December 03 Key West
  • City of Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park. Seeing Santa is a highlight for kids.

  • December 03 Key West
  • Friends of the Key West Library Book Sale
  • Website
  • The Friends of the Key West Library will hold the December Book Sale outside in the library's Palm Garden on Saturday, Dec. 3, from 10am-1pm. Most books are priced at $1, although for this sale, there is a nice selection of art books suitable for holiday gifts priced in the $10-20 range. 700 Fleming Street.

  • December 03 Key West
  • Pet Pictures with the Grinch
  • Website
  • Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street from 11 a.m. to 2 p.m. for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary.

  • December 04 Key West
  • Key West Woman's Club Holiday Open House
  • Website
  • Members have decked the halls of the historic mansion at 319 Duval Street for all to enjoy at Sunday's open house from 4 to 6 p.m. Enjoy appetizers, desserts and Amsterdam eggnog, and an appearance by Santa. Music from the Bahama Village Children's Choir and the Key West Community Orchestra. Official tree lighting by Mayor Teri Johnston. Donations of new, unwrapped clothes for students ages K-12 are appreciated.

  • December 04 Key West
  • Pet Pictures with Santa
  • Website
  • Pack up Fifi and Fido and delight in Pet Pictures with Santa Sunday, Dec. 4 from 6 to 8 p.m. at the Christmas tree at the foot of William Street at the Key West Bight Marina. Proceeds benefit the Boys & Girls Club of the Keys.

  • December 04 Key West
  • Eaton Street Christmas Stroll
  • Website
  • Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts and the Key West United Methodist Church unite for the annual Eaton Street Christmas Stroll. Each venue hosts a short Christmas-themed performance with caroling as you walk from presentation to presentation. At The Studios of Key West, sip Christmas cocktails with a view and get an extra chance to catch the Members Show for some holiday shopping. The Stroll begins at 4 p.m. at St. Paul's.

  • December 04 Key West
  • Key West Artisan Market: 10th Anniversary Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and breathtaking ocean views as we celebrate 10 years of the Key West Artisan Market with old and new friends. Also supporting Friends of the Aids Memorial which is located across the street at White & Atlantic at the entrance to the Edward B. Knight Pier. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.


  • December 07 - 11, 2022 Key West
  • Nutcracker Key West
  • Website
  • A unique subtropical version of the classic holiday ballet "The Nutcracker" awaits Keys visitors, flavored with characters and settings that depict Key West's colorful history, vibrant coral reef environment and even free-roaming local roosters. Blending professional dancers and local talents, the production features exquisite costumes and sets inspired by island lore. Performances take place at the Tennessee Williams Theatre at 5901 College Road.

  • December 09 Key West
  • Holiday Historic Inn Tour
  • Website
  • During this enchanted Friday evening, visit and tour four beautifully decorated island locales: Key West Butterfly & Nature Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation between 6 and 8 p.m. Explore the unique architecture and history at each stop while enjoying sweet and savory holiday treats and libation samplings. Limited trolley transportation will be provided between properties, but participants are encouraged to bike, walk or use their own transportation. Purchase tickets online, then pick up tickets after 5 p.m. on Dec. 9 at Butterfly & Nature Conservatory.

  • December 10 Key West
  • Ninth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park in Key West from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2022 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.

  • December 10 Key West
  • Schooner Wharf Annual Key West Lighted Boat Parade
  • Website
  • A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights. Music begins at 6 p.m., parade starts at 8.

  • December 11 Key West
  • Key West Triathlon
  • Website
  • The Key West Triathlon challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike and sprint duathlon competitions are featured. Higgs Memorial Beach Park, 1000 Atlantic Boulevard, Key West.

  • December 16 - 17, 2022 Key West
  • The 12 Days of Christmas: Burlesque Show Spectacular
  • Website
  • This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members. Doors open at 7 p.m., show at 8. Tickets $45 to $100, available online. Key West Theater, 512 Eaton Street.

  • December 16 Key West
  • Holiday Historic Inn Tour
  • Website
  • Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8 p.m. Purchase tickets online, then pick them up after 5 p.m. on the night of the tour at the first property, Hemingway’s Library at Papa's Pilar Distillery. Participants will need to walk, bike or use their own transportation between locations.

  • December 17 Key West
  • Key West Botanical Garden Native Plant Sale
  • Website
  • The plant nursery offers native Florida trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month. Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

  • December 17 Key West
  • 14th Annual 5K Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join! Starts and ends at Southernmost Beach Café, 1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 16 from 5-7 p.m. at the Café. Runners and walkers of all ages and abilities are welcome to participate. Registrants receive a free t-shirt; prizes for most festive and unusual PJ’s. Presented by nonprofit group, A Positive Step for Monroe County.

  • December 18 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and splendid ocean views as we offer everything you need to cross off your holiday shopping list. Supporting the Key West Shop Mom & Pop and #shoplocalkey west movement to keep our resources right here in our community. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.

  • December 18 Key West
  • Key West Lighting of the Menorah
  • Website
  • The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.18 from 5 to 6 p.m. 1320 Truman Avenue.

  • December 28 - 29, 2022 Key West
  • Old Island Restoration Foundation's Home Tours "Holiday Style"
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 63rd series of tours features self-guided tours of homes festively dressed for the holidays on Dec. 28 and 29. After the holidays, home tour dates are Jan. 13-14, Feb. 17-18, and March 17-18. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • December 31 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2023 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.

  • December 31 Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.

  • December 31 Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

  • January 05 - 08, 2023 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters from ages 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Higgs Beach, with the main event Saturday. Prize monies for male and female challengers are up for grabs, including additional prize money for any man or woman who breaks the island record. Pancake Breakfast from 8 am – 10 am. Admission Free. Pancake Breakfast tickets are sold onsite.

  • January 07 Key West
  • Pancake Breakfast - Higgs Beach
  • Website
  • 8 am – 10 am in support of the Key West High School Track Team and the Mays Sands Montessori School. Pancake Booth is located near the African Cemetery and at the Pole Vault in Paradise competition. Unlimited pancakes and one mimosa (adults only) are included. $20 Adults, $10 Children Tickets at the website and on the day of the event.


  • January 12 - 15, 2023 Key West
  • Key West Literary Seminar
  • Website
  • Each year, the Key West Literary Seminar features a particular theme. "Singing America," the 40th seminar, will center on Black American experiences through poetry, fiction, biography, and history. From slavery and Reconstruction to the Harlem Renaissance, the civil rights movement, today, and into the future. Find information and registration online. Event takes place at 717 Love Lane, Key West.

  • January 12 - 15, 2023 Key West
  • Key West Kingfish Mayhem
  • Website
  • This the first tournament of the five-leg Kingfish Mayhem Pro Series. In the winter, Key West is the staging ground for King Mackerel before they start their annual migration in the Gulf. Big fish from the 50-70 lb. range are common in these areas, which creates an exciting and competitive environment at the weigh-in. This event has been enhanced by adding tuna, mahi and wahoo, for a four-species tournament. Teams from all around travel to join this world-class event for their shot at claiming King of Key West!

  • January 13 - 14, 2023 Key West
  • Old Island Restoration Foundation's 63rd Annual Key West Home Tours
  • Website
  • Enjoy tours of beautiful and historic Key West homes and gardens. Your ticket purchase supports the ongoing mission of preserving and promoting Key West's unique architecture, culture and history. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.

  • January 13 - 15, 2023 Key West
  • 25th Annual Key West Half Marathon & 5k Run
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2023 25th anniversary race follows a 13.1-mile course that includes Old Town Key West and the scenic waterfront. The race typically attracts American and international runners to compete in Key West's balmy January climate. Ranked among 13 must-do U.S. half-marathons by Competitor.com.

  • January 14 - 15, 2023 Key West
  • 17th Annual Florida Keys Seafood Festival
  • Website
  • Bring the whole family for the freshest seafood caught, cleaned, prepared and served by local fishermen. This event is a fundraiser for the Florida Keys Commercial Fishermen's Association FKCFA and goes to support sustainable fishing programs, marine restoration projects and college scholarships. A $10 admission is good for BOTH Saturday and Sunday and the festival is to be held at Bayview Park.

  • January 16 - 20, 2023 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.

  • January 17 - 21, 2023 Key West
  • RokIsland Fest 2023
  • Website
  • Staged at the Truman Waterfront Park Amphitheater, the world’s greatest rock bands descend upon the island of Key West for this 4-day music festival in paradise. Single- and multi-day passes available. Performers include Styx, Tesla, Loverboy, Vince Neil, 38 Special, Queensryche, Stryper, Quiet Riot and more.

  • January 24 - 20, 2023 Key West
  • Mile 0 Fest Key West
  • Website
  • Mile 0 Fest Key West is a "must see" boutique destination music festival in the burgeoning Red Dirt & Americana music scene. Take in big shows at Truman Waterfront Park Amphitheatre, a state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Many activities and memorable experiences await.