Annual Events in Clearwater, FL

The residents in Clearwater sure do know how to get celebratory, and this is evidenced in their multiple festivals and annual events. From musical events to food fests, historical celebrations to cultural events, there is always something going down in Clearwater. Below are some of the biggest annual events in Clearwater, FL, with the range spanning from wacky to whimsical!

Solar Company Clearwater FL

  • Clearwater Jazz Holiday

Enjoy the best that Clearwater has to offer at this jazz holiday that goes on for an entire 4 days! Allow yourself to get lost in the sea-salty air and warm breezes that are only found in Clearwater. Everything about Clearwater Jazz holiday, both music-wise and people-wise, seems to take you away to a place where the ambience is just warm and lovely. Get to enjoy your favorite jazz jams from renowned local and regional artists.

  • Clearwater Offshore Nationals

For boat races like none other, be sure to attend the Clearwater Off-shore Nationals, taking place every year in September. The boats featured in the event all come equipped with 6000-horsepower engines and F-16 jet canopies, and they race at speeds not less than 170 MPH. If boat races are your thing, then you know just where to head. This annual event off the Clearwater Gulf of Mexico attracts over 180,000 visitors from all over the country. Not only will you be treated to crazy boat ride thrills, but this September festival also features live entertainment, food vendors and exciting parades.

  • Clearwater Beach Chalk Art Festival

The Chalk Art Festival in Clearwater, FL, is a fun festivity that is absolutely free! This event has been held in Clearwater for 9 years, and its main aim is offering local, regional, upcoming, and student chalk artists a chance to showcase their wonderful works of art, while inviting the public to enjoy chalk art at its best. Community-minded Art enthusiasts, in collaboration with the Beach Chambers’ Chalk Art Festival Committee, come together to ensure that this event is a success. For 3 days, more than 40 super talented chalk artists transform South Clearwater Beach’s sidewalks into a magnificent display of canvases, allowing the public to take a gander into the entire art production process, from one step to the other. The public then gets to choose their favorite piece by taking a vote at the ‘People’s Choice Award’. The winner gets announced on the last day of the event at noon.



5 min
1.2 miles

via S M.L.K. Jr Ave and Druid Rd

Best route, despite the usual traffic

5 min
0.9 mile

via S M.L.K. Jr Ave and Turner St

5 min
1.2 miles

via N Myrtle Ave

Some traffic, as usual