Festivals & Events

Festivals & Events

While September and October might be during the off-season in the Sunshine State, they’re far from quiet! There’s always plenty to do, from small craft markets to huge music celebrations. Whether you’re a tourist or a local, laid back or adventure seeking, here are twelve events you simply can’t miss! 


I Like It Hot! Festival 
Sept 14-15 

Kicking this list off with a bang is the 19th annual I Like It Hot! Festival, the spicy foodie’s dream event! Whether you like to keep things cool with mild dishes or you prefer to feel the burn in every bite, this festival is the place for you. Home to all the hottest dishes, you’ll get to try your luck against the spice in all sorts of forms: salsas, sauces, jerkies, even lollipops – and of course, raw hot peppers that will have steam coming out of your ears! You can even test yourself against your fellow foodie by entering competitions such as the raw hot pepper eating contest. This event does offer non-spicy dishes as well as live music, and only costs $5 admission, with kids and parking free of charge. It’s a true spice paradise!  


27th Annual Biketoberfest® 
Oct 17-20 
Daytona Beach 

Join over 100,000 bikers and motorcycle enthusiasts at this annual Daytona Beach motorcycle rally! Watch the exciting motorcycle racing at Daytona International Speedway and listen to invigorating live music while enjoying the prime weather. October in Daytona Beach is a dream of warm sun and cool breezes, perfect for spending your time outside experiencing the thrill of live racing and touring the most scenic routes in Central Florida. 


Fantasy Fest 2019 
Oct 18-27 
Key West 

Whether you love to harmonize or march to the beat of your own drum, you’ll fit right in at Fantasy Fest. Their monumental celebration for their 40th anniversary welcomes everyone; from alto to soprano to tone deaf, you’re all invited to the performance of a lifetime. Don your best costume, no matter if it be an elf or a warrior or a rock star. Bring your best dance routine or go freestyle, and be prepared to bellow to your favorite oldies or jive to the latest hits. At this annual 10-day nonstop party for grown-ups, anything goes, so long as everyone is feeling the beat and having a good time! This wild extravaganza welcomes revelers from all over the world to bring their imaginations and best pair of dancing shoes, and get ready for 10 days of costumes, parades, libations, and a whole lot of memories!  


Clearwater Jazz Holiday  
Oct 17-20 

Join the 40th annual celebration of the Clearwater Jazz Holiday! For four days and four nights, you can join over 35,000 people in this live, world-class music festival in the beautiful Coachman Park. Enjoy your favorite artists and discover new ones against the backdrop of one of the world’s greatest beaches, right on the glittering Gulf of Mexico. What started as a series of concerts in the back of a flatbed truck evolved into what is now an annual music festival pulling tens of thousands of international guests each year, featuring combinations of legendary and contemporary artists and a diverse community of music enthusiasts.  

25th Annual Downtown Sarasota Craft Festival  
Oct 5-6 

It’s time to get your craft on! Along the famous white sand beaches of the Gulf of Mexico lies Sarasota, a city known for its beautiful culture, architecture, and museums, among much else. You too can get involved in the culture and artistry of the city by visiting the Downtown Sarasota Craft Festival, which has garnered much love from fine craft lovers all around. This festival has something that will appeal to everyone – from jewelry, pottery and ceramics to photography, painting and clothing, and whatever else might spark your crafty interest. Do you have a green thumb? This festival also includes the Green Market, home to plants, exotic flora and handmade soaps, as well as temptations such as gourmet spices and freshly popped kettle corn! Spend the whole day to your crafty heart’s content – free of admission.  


Clearwater Jazz Holiday 
Oct 17-20 

Where better to enjoy four days of jazz and blues other than the sunny, breezy air of Clearwater? This festival is a celebration of the most American music, and the soulful people who take part in it, whether they’re on the stage or in the crowd. Four beautiful fall days and cool nights will be filled with the sounds of top musical performers. The Clearwater Jazz Holiday has been home to legends such as Gladys Knight, and ranges from Count Basie Orchestra to Sheryl Crow, amongst other must-see performances.  


John’s Pass Seafood and Music Festival  
Oct 18-20 
Madeira Beach 

If you’re looking for an authentic taste of Florida, John’s Pass Seafood and Music Festival invites you to celebrate 38 delicious years of fresh local seafood and music. This festival is a true tribute to the strong community surrounding it and is dedicated to giving back to it and enriching the culture, and invites you to take part, free of charge! Support the local seafood industry at this premier seafood festival, full of mouthwatering seafood and show-stopping live music. Enjoy three days of shopping, dining, and entertainment – and don’t forget to bring your spookiest costume for a chance to win the $5,000 at the Halloween Block Party! 


Sushi and Stroll 
Sept 13  
Delray Beach

Nothing is better than indulging in some mouthwatering sushi made from the freshest local seafood – except perhaps doing so while taking a leisurely stroll through beautiful gardens, spurred on with a thundering performance by taiko drummers from Fushu Daiko! At the Sushi and Stroll, held in Morikami Museum and Gradens, you will excite your palate with the delicious selection from various unique food trucks, or indulge in the museum’s Cornell Café. For all you adults out there, you can cool off in the late summer sun by sipping at some ice-cold Japanese beer and sake! Feel free to visit the Museum Store for some unique keepsakes, or take a self-guided audio tour of the gardens through the Morikami app. 


New Smyrna Beach Jazz Festival 
Sept 26-29 
New Smyrna Beach 

One of Central Florida’s premier music events, the New Smyrna Beach Jazz Festival is celebrating their 19th anniversary – and this year will be bigger and louder than ever! This lively three-day event is filled with the best of jazz, the tastiest of foods, and the most fun. Concert-goers can spend all day at this perfect location hopping from club to club to get a full range of music and entertainment, spanning Flagler Avenue from the Atlantic Ocean to the Indian River! But it doesn’t end there – the festival has expanded over the years to include many more streets such as Third Avenue, Canal Street, Atlantic Avenue and the North Causeway, so that your fun can last all day and well into the night. There’s never a dull moment at this festival, as even if you want a break from all the dancing you’ll be doing, you can explore the beautiful area of New Smyrna Beach!  


Miami Carnival 
Oct 13 

Set in a kaleidoscope of color, this breathtaking weekend event is so rich and diverse it’s hard to put into words! Be sure to set aside time to see all that this festival has to offer – none will disappoint. Packed with all sorts of competitions kicking things into high gear with the Carnival and Kings, Queens and Individuals Show. Expect to see a whole lot of color, and more feathers and beads than you ever have before. Kings and Queens will be wearing their breathtaking and unique costumes, iconic cultural pieces that can sometimes reach up to fifteen feet wide and twenty feet tall! Get ready for the march of your life at the Parade of the Bands, a parade that can go over eleven hours and is comprised of more than 18,000 masqueraders and 20 masquerade bands. Don’t forget to visit all the stages, concerts, and expos, as well as the extensive Arts and Crafts portion – you’ll be sure to leave with some souvenirs. All that celebration is sure to work up some hunger, and luckily there’s an extensive and authentic selection of food, drink and libations from the Caribbean region.  

REEF Fest 
Oct 17-20 
Key Largo 

Are you intrigued by marine education, or interested in learning about it first-hand, in a real environment? REEF Fest is perfect for you! This four-day celebration focuses on the success of marine conservation and education initiatives locally. Take part in diving and eco-adventures alongside the most prestigious names in diving and marine conservation, as well as attend educational seminars and social gatherings. There will be socials every evening of the festivals, which are free and open to everyone – the whole festival is, welcoming all those who are interested, although pre-registration is preferred. If you want something a little more exclusive, the For the Love of the Sea Banquet is a ticketed dinner.  


Island Hopper Songwriter Festival  
Sept 20-29 
The Beaches of Fort Myers and Sanibel 

The 6th Annual Island Hopper Songwriter Festival is a diverse music festival hosted by iHeart Radio and BMI, taking place all across For Myers and Sanibel, home to beautiful beaches and colorful cultures. The festival takes place in a wide selection of hotels and resorts – the perfect opportunity to book early and be steps away from your favorite artists as well as yet-undiscovered ones. Just sit back and relax on the gorgeous island beaches as you take in the live music; this is what Florida is all about.  


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