There are lots of things going on in Key West as the party never truly stops…but here are some Fall and Winter events that you should keep an eye out for as you book your next trip. And there is something for everyone from comedy nights, fantasy fest, headdress ball, several parades (marches), racing, festivals, music, crafts, booze, and even more festivals. Take a look at some of the best events in Key West and keep a look out for our feature posts to learn more about these as the fall and winter continue on.
Comedy Key West Presents Comedians Every Weekend
If you hate hitting your funny bone but love to laugh out loud then the Comedy Key West calendar is home to some great comedians that you won’t want to miss. There are local comedians opening for the national acts so it will be a late night you won’t forget! Many of the featured comedian nights are hosted by none other than Tom Dustin who has been featured on Comedy Central and took home the top prize on The Great Canadian Laugh-Off show. There are too many events to feasibly put in this post so go check out the fall and winter schedule now by clicking here.
Scarecrows in the Forest | Sept. 15-Nov. 30
“The Key West Tropical Forest & Botanical Garden’s annual Scarecrows in the Forest event features locally designed scarecrows from individuals, creative professionals, organizations and businesses.” Celebrating creativity and upcycling creators can use natural and recycled items to build their scarecrow masterpieces. The winner gets a cash prize for each of the following categories: school-age groups; not-for-profit groups; and businesses, amateur individuals and creative professionals. Come out and enjoy a nice art display between Sept. 15 and Nov. 30. Your vote counts as the “Best in Show” is picked by garden visitors. You can find out about admission costs and more by clicking here.
Fantasy Fest 2022 | Oct. 21-30
Fantasy Fest was founded in 1979 by Bill Conkle, Joe Liszka, Tony Falcone, and Frank Romano. We all know the party is always pumping in Key West today but back in the 1970’s the winter season was always dead and businesses suffered. So these four local business owners came up with an event idea based around costumes and parades and Fantasy Fest was born! There is more to the story but we will let them tell it so click here for more info on this outrageous party extravaganza!
2022 Royal Coronation Ball | Oct. 21
This two-hour stage show includes a three course plated meal, a cash bar, local celebrities, and contestants performing at the famous Coffee Butler Amphitheater in Key West. “Enjoy a party with Key West’s Royal Family and cast your vote for the King & Queen of Fantasy Fest!” This is a benefit for the A.H. of Monroe County, Inc. Click here for more info!
Bahama Village Goombay Festival | Oct. 21-22
This free island street party features music, arts and crafts, and food. The bands range from gospel to reggae and will be showcased at the corner of Petronia and Fort Street. This is a family friendly event so come on down! Click here for some info on being a vendor at this amazing street party!
39th Annual Headdress Ball | Oct. 27
The 39th Annual Headdress Ball is presented by the Key West Business Guild and is held at the Coffee Butler Amphitheater. “See talented headdress makers, judged from the shoulders up, compete for the first place prize of $3,000, second place of $1,000, and $500 for third place. Eight great talent acts will also be featured. Laurie Thibaud of Aqua Idol fame returns as emcee. Bar and food service available during the performance.” The monies from this event are used to promote LGBTQ+ tourism. Click here for more info.
Masquerade March | Oct. 28
In conjunction with the Fantasy Fest week-long celebration the Masquerade March is widely known as the “locals’ parade” and features community, costumes and the creative side of its participants. This, “grown-up moving cocktail & dance party that begins at the Frances Street entrance of the Key West Cemetery. This moving mosaic of costumed revelers strut their wacky costumes on a route that winds its way north to Fleming Street stopping at participating guest houses, which – while supplies last – hand out complimentary beverages.” Check out all the info by clicking here.
Bud Light Fantasy Fest Parade | Oct. 29
The Bud Light Fantasy Parade’s theme is “Cult Classics & Cartoon Chaos!” Cash prizes totaling in upwards of $15,000 make this a spectacular parade where all the participants really go all out to make sure their presentation is flawless. “The parade is a splendid moving party with festive floats, wild walking groups, bicycle brigades, and even human-powered kinetic machines that entertain tens of thousands of spectators in the premier Fantasy Fest event.” Don’t miss out on this amazing event. Click here for more info.
Powerboat Races by Raceworld Offshore | Nov. 6-13
Your need for speed will be quenched at the Powerboat Races presented by Raceworld Offshore. This weeklong celebration brings fans and teams from all over. There are lots of fun activities throughout the week including the races, boat parties, concerts and more! To get the full schedule and all that is in store for this championship race week go here.
Key West Holiday Fest | Dec. 1 – Jan. 1
This is a month-long journey of festive holiday events that showcase parades, (on land and sea), Harbor Walk of Lights, seasonal arts and crafts markets, train and trolly tours and so much more. Everything you need to know is right here…
COAST is CLEAR Music and Arts Festival | Dec. 1-4
This event was founded (2017) by Coast Projects and the festival is co-produced by Key West Art & Historical Society. This festival was created to lift the spirits of the locals after hurricane Irma reacted havoc on Key West. This year’s bands feature Shakey Graves, Hiss Golden Messenger, Fruit Bats and so many more! Check out the tickets prices, times and locations here.
KWAHS Annual Holiday Concert & Bazaar | Dec. 9
The Key West Art & Historical Society presents it’s Annual Holiday Concert & Bazaar on Dec. 9th. “The immensely popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House.” They are still taking vendor applications so if you want to sell some art or participate in this event check out the link here.
Ninth Annual Florida Keys SPCA Parade of Paws | Dec. 10
Heading into its 9th year the Florida Keys SPCA Parade of Paws is an event that gets two paws up! Come on down to the Higgs Dog Park in Key West as local four pawed friends will be strutting their stuff in this family friendly event! Local vendors, live music and canine friends make this a great day indeed! Costumes are not required but welcomed! Check out the link for more info.
14th Annual 5K Rudolph Red Nose Run | Dec. 17
Running is fun but it’s even better when it’s for a good cause! This 5k is put on by the local non-profit A Positive Step of Monroe County. Their mission is to serve, “Monroe County’s highest risk kids and their families since 1999 and the Key West Southernmost Runners Club.” These types of events are crucial to the community at large so your support is greatly appreciated! Check out this link to register to run!
New Year’s Eve: Conch Shell Drop at Sloppy Joe’s | Dec. 31
Local famous bar “Sloppy Joe’s” knows how to throw a party! Aside from this event, which features live music and a conch drop to celebrate the New Year…they also throw parties almost every night of Fantasy Fest week. So check those out here if you are ready for a wild night in Key West!
2023 Soldier Ride Key West | Jan. 6-8
The Wounded Warrior Project is a great cause that works with veterans (warriors) and their families through different events. One of these events is the Soldier Ride which is a, “unique, multi-day riding event that helps warriors build their confidence and strength through shared physical activities and bonds of service in a supportive environment.” This event is open to warriors of all types of skill sets and fitness levels. All equipment is provided and there is no cost!
Florida Keys Seafood Festival | Jan. 14-15
This festival was created 17 years ago to bring the community together so the local fishermen and women can showcase their catch in various forms of delicious seafood dishes. Tickets are only $10 for adults and kids 12 and under are free! Check out more info here and purchase your ticket today!
25th Anniversary Key West Half Marathon & 5K | Jan. 15
This year marks the 25th anniversary of the Key West Half Marathon & 5k! This storied event is a staple for Key West local racers and beyond. This five day event is chalked full of fun including a meet and greet, pasta dinner, concert and awards party, and farewell party with live music and more! To register please check out this link.
RokIsland Fest 2023 | Jan. 17-21
What is RokIsland Fest? As described on its website, “the world’s greatest rock bands descend upon the island of Key West for a 5-day music festival in paradise.” Sign me up! Headlining the fest are prog/hard rock legends Styx, Tesla, Loverboy and Vince Neil. With a total of 19 hard rock bands this is sure to rock your socks off so pack an extra pair! You can buy tickets here.
Mile 0 Fest | Jan. 24-28
The Mile 0 Fest features the best Red Dirt & Americana bands for this 5-day festival located in the heart of Key West. The festival brands itself as a “boutique destination festival” and its fans say it’s, “the friendliest and best fest out there!” To check out the slam packed band lineup go here to read all about it!
37th Annual Key West Craft Show | Jan. 28-29
The 37th Annual Key West Craft Show brings together 100 fine craft vendors who are carefully selected to provide a wide variety of crafts. This show is open to the public and goes from 10:00 a.m. to 5:00 p.m. Check out more info here.
Key West Food & Wine Festival 2023 | Jan. 25-29
What sounds better than samples of wine and tasting the finest foods for a week? Every year the Key West Food & Wine Festival showcases amazing wine from around the world and creative treats to pair nicely with a week of sun and fun in Key West. To get tickets and more info please visit here.
58th Old Island Days Art Festival | Feb. 26
The Key West Art Center is the show-runner for the Old Island Days Art Festival. The festival, in its 58th year, “has grown from about 20 local artists gathering around the Customs House to nearly 100 artists from near and far spreading up Whitehead Street and on to Caroline Street in the beautiful Truman Annex gated community.” For more info on this family filled outing check the event page here.