Fall Events and Festivals

Every time of year is special in St. Pete/Clearwater but the fall season brings its own brand of magic with spectacular weather that simply makes you want to hang out with others and celebrate the best of what the area has to offer.

Fortunately, there's no shortage of occasions to do just that. Renowned music festivals, like the Clearwater Jazz Holiday, give you cause to tune out the hubbub of daily life and lend an ear to some of the world's most renowned musicians. And area villages, such as John's Pass, put their very best foot forward with to-drool-for festivals that remind you just how delicious the food and arts are here. Events like these add memorable highlights to what's sure to be an already unique vacation.

1 GeckoFest

Saturday, September 3, 2016

Explore the quirkiness of Gulfport at the annual Geckofest over Labor Day Weekend. Browse great art, listen to live music and check out some street performers along Beach Blvd.

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2 Clearwater Super Boat Races

Friday, September 30 - Sunday, Oct. 2, 2016

Get ready for 180 mph of fun! Head down to Clearwater Beach for a speed-tastic view of this year's Clearwater Super Boat National Championship & Festival!

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3 Clearwater Jazz Holiday

Thursday, October 13 - Sunday, October 16, 2016 

Bring your chairs and blankets and relax to the soothing sounds of jazz from world-class musicians complimented by beautiful waterfront settings. Stay tuned for this year's line up! Last year's event featured nine-time Grammy winner, Sheryl Crow. Past performers have also included blues legend Buddy Guy, Americana favorites the Avett Brothers, classic soul performer Gladys Knight and more!

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4 Oldsmar Oktoberfest 2016

Friday, October 21, 2016 – Sunday, October 23, 2016

Walk through the doors of the Oktoberfest Village and be transported to a world of family fun, good times and good cheer! Authentic German food and beer will be served by friendly staff wearing traditional German attire!

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5 Clearwater Chalk Festival

Friday, October 21, 2016 – Sunday, October 23, 2016

Watch beautiful art come to live at the Clearwater Chalk Art Festival on Clearwater Beach! A kid zone, arts & crafts vendors and more will be on site over the three days. Bring the whole family for some fun in the sun!


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6 John's Pass Seafood & Music Festival

Enjoy fresh gulf seafood, live music and more at this four day celebration in historic John's Pass Village on Madeira Beach. Festival highlights also include a Halloween Block Party with costume contests on Friday, the Battle of the Gulf Fishing Tournament on Saturday, and the World's Largest Bloody Mary Toast on Sunday morning. 

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7 St. Pete Wine & Food Fest

Wednesday, November 2, 2016 – Sunday, November 6, 2016
Celebrate all things food & wine over five days in downtown St. Pete! Enjoy a wine pairings dinner, a taco & tequila tasting with margarita making, a craft beer night and two days of grand tastings featuring wine from around the world and fare from Tampa Bay's best restaurants and chefs.
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8 Ribfest

Friday, November 11 - Sunday, Nov. 13, 2016

Head to Vinoy Park in downtown St. Pete for this three-day festival where you'll enjoy live music from nationally touring bands, family-friendly activities, and the best barbeque ribs in the world. 

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City: Gulfport

3129 Beach Blvd. S
Gulfport, FL 33707

Phone: 727-322-5217

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4Upper Tampa Bay Oktoberfest

City: Oldsmar

11225 Race Track Rd
Oldsmar, FL 33626

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55th Annual Clearwater Beach Walk Chalk Walk

City: Clearwater Beach

333 S. Gulfview Blvd.
Clearwater Beach, FL 33767

Phone: 727-447-7600

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7St. Pete Wine & Food Festival

City: St. Petersburg

Downtown St. Petersburg
St. Petersburg, FL 33701

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