Five Fab Fall Fests

As the autumn equinox approaches, the fall season in Florida is marked by shorter days, clearance sales on sandals, and a bounty of fall festivals. Fests below are our favorite picks for 2018.


Island Hopper Songwriter Fest
Sept. 21-30 on the beaches of Fort Myers and Sanibel
Island Hopper courtesy of the Beaches of Fort Myers & Sanibel

The 10-day Island Hopper Songwriter Fest, one of the Southeast Tourism Society’s Top 20 Events for 2018, provides a chance to hear and meet musicians who craft chart-topping country hits.

Dozens of songwriters will partake in the event which offers new experiences this year including resort pool parties, wine pairings, house parties and a songwriter workshop.

The 5th annual festival kicks off on Captiva
Island, just north of Sanibel Island, Sept. 21-23. It then moves to downtown Fort Myers Sept. 24-27 and wraps up on Fort Myers Beach Sept. 28-30. The Texan country music band, Midland, headlines the event. Top singer/songwriters include Earl Bud Lee (Friends in Low Places by Garth Brooks), Dylan Altman (Barefoot Blue Jean Night by Jake Owen), Lee Thomas Miller (Whiskey and You by Chris Stapleton), Wendell Mobley (There Goes My Life by Kenny Chesney) and many others.

Download the new official Island Hopper mobile app. Most of the performances
are free; a few require a ticket.

Oktoberfest Tampa
Oct. 12-14 at Curtis Hixon Waterfront Park
Enjoy Tampa’s Oktoberfest

Eat some brats, drink beer and wine, play
Bavarian games, and do not miss the Beard and Mustache Competition, a serious showdown of facial hair, talent and style, all at the 9th annual Oktoberfest Tampa.
Set in an urban park along 
the Hillsborough River, it’s a lovely way to enjoy German eats, live alphorn performances, oompah
music and Schuhplattler dancing.

Games are free. Admission $10, $25 weekend; free for military, first responders and those 12 and under. Festival is pet-and family-friendly.

Clearwater Jazz Holiday
Oct. 18-21 at Clearwater’s waterfront Coachman Park
The Doobie Brothers

A Friday tribute to the flamboyant musical icon Prince and a Saturday performance by the Doobie Brothers mark the 39th annual Clearwater Jazz Holiday. The four-day extravaganza is produced by Clearwater Holiday Foundation, a not-for-profit
organization which raises money for year-round educational programs.

Headliners include Sheila E., Morris Day and the Time, George Thorogood and the Destroyers, JJ Grey & Mofro, Mindi Abair & the Boneshakers, the Devil Makes Three, the Lao Tizer Band featuring Chieli Minucci, Karen Briggs & Nelson
Rangell and many more.

Food and merchandise vendors, a Saturday night fireworks display, and an
after-party at the Capitol Theatre round out the event. Tickets start at $20 with VIP packages available.

Sun Fiesta
Oct. 19-21 at Airport Festival Grounds in Venice
Venice’s Sun Fiesta

Besides being a special treat for the locals, the Sun Fiesta welcomes home the snowbirds – and in Venice, that’s a
pretty big flock. The celebration normally draws up to 40,000 attendees annually.

Now in its 45th year, the fiesta is the top fundraiser for the Women’s Sertoma Club of Venice which provides scholarships and monies for charities.

Please note: the location has been moved this year to the Venice Airport Festival Grounds.

There’s a new 5K race at 7:30 a.m. Sunday that will be followed by a pancake

Perennial favorites like the Miss Sun Fiesta Pageant, the bed races, the dunk
tank, live entertainment and the parade will return this year along with food,
merchandise, beer and wine vendors.

Sarasota Medieval Fair
Weekends of Nov. 3-18, in the Ringling Woods behind the Sarasota Fairgrounds
Sarasota Medieval Fair

Come and meet the heroes and oddities of ancient humanity including wenches, knights, jesters, minstrels, belly dancers and soothsayers during the 15th annual Sarasota Medieval Fair.

The artisan marketplace features over 100 shops, food and snack booths where you can pick up your own period costume, get a henna tattoo, down a meat pie and wash it
down with beer or mead.

Partake in a pub crawl, listen to Celtic music, and enjoy human combat chess matches, knife-throwing and jousting exhibitions. Watch the daring (and slightly crazy) Ichabod Wainwright navigate the Wheel of Death. Step into your own adventure with this year’s Norse Vikings scenario.

Lots of fun for the whole extended clan.
See the website for a 
variety of ticket options.






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