The weather in Florida right now is glorious. We rarely get temperatures this cool at this time of year (Halloween can be tricky when you're burning up in those heavy costumes). However, because things have generally cooled down a bit, this is the time of year when you'll find multiple festivals every weekend. Last weekend for example, there was Clearwater Jazz Holiday, an Octoberfest at the local Catholic church, an antique car show, and the "Taste of Dunedin" all within a 10 mile radius.
Most of the towns in the Tampa Bay area have a full schedule of events throughout fall (and spring). Part of the reason we chose Dunedin was that we found ourselves visiting for some event or another almost every weekend when we moved to the area.
If you are planning a trip to the area (oh, or if you live here!), here are some resources to find out what might be going on (or to plan when to visit):
Old Palm Harbor Main Street website: events in downtown Palm Harbor, Florida
St. Petersburg, Florida official site: events in St. Pete (today there is more than one thing listed for almost every hour!)-events are color-coded based on the type of event
Island Time: links to the various towns' events calendars plus more festivals throughout Florida
Dunedin Wines the Blues is one festival I would highly recommend, whether you like good blues music, wine or just a general good time in a fun, downtown atmosphere. For all of the events happening in Dunedin, visit the city of Dunedin events calendar.
In addition to the Clearwater Jazz Holiday, which is one of the area's premier events for locals and out-of-town visitors, you can find a variety of arts events, crafts shows, great music festivals, beer events, sporting events (we loved going to the Indy car races in St. Pete), and unique local celebrations such as Stone Crab weekend at Frenchy's Restaurants and the Palm Harbor Citrus Festival. The Strawberry Festival in Plant City is one of the most delicious!
Because of the beautiful weather and scenery, you'll find some type of outdoor celebration on almost any night. For example every evening, Sunsets at Pier 60 on Clearwater Beach has live music/entertainment, arts and crafts and (free!) one of the most striking sunsets you will ever see.