Event Calendar
From Halloween nights at Busch Gardens to fall festivals, live music, and community gatherings, here's what's happening across all three markets this season. And your next home might be closer than you think.
Fall in Tampa Bay, Ocala & Gainesville: Your Local Events Guide
Fall in Florida means cooler evenings, pumpkin patches, and a full calendar of festivals across our three markets. From craft fairs at the Shops at Wiregrass to Eagles classics at Circle Square, there's no shortage of reasons to love living here this time of year. This season we're hosting two of our own: Headshots & Espresso Shots, a midday mixer in Ocala on October 16, and Otoño a lo Cubano, our free fall festival with a Cuban flair in Tampa on October 25.
At Solara Real Estate, we believe the right neighborhood is more than square footage. It's the events on your calendar, the people you meet, and the life you build. We've rounded up the best fall 2026 events across Tampa Bay, Ocala, and Gainesville, and if any of them make you think “I'd love to live closer to this,” we're ready to help.
Tampa Bay Fall Events 2026
Flyer art by LisArte (@lisarte13)Otoño a lo Cubano
Un festival de otoño con sabor cubano
Leto High School (gym parking lot), 4409 W Sligh Ave, Tampa, FL 33614 · Free entry & free parking
Our fall festival with a Cuban flair, presented by Solara Social and La Gozadera Tampa. A full day of food, music, culture, and family, and every free ticket enters you in our raffle.
Howl-O-Scream at Busch Gardens
HalloweenSelect nights through Nov 1 · Gates 5 PM, event 7 PM · Busch Gardens Tampa Bay
Tampa's biggest Halloween event returns with haunted houses, scare zones, live shows, and the park's coasters running after dark. It's a separately ticketed night event geared toward teens and adults. No costumes allowed, and the scares run intense.
View Event DetailsCandy Crawl at The Shops at Wiregrass
Free10:00 AM to 2:00 PM · The Shops at Wiregrass, 28211 Paseo Drive, Wesley Chapel
Bring the kids in costume for a free Halloween stroll through Wiregrass, with free treat bags for the first 500 kids and free pumpkins to decorate. An easy, walkable fall morning right in the heart of Wesley Chapel.
View Event DetailsArmature Works Fall Festival
Family12:00 to 5:00 PM · Armature Works West Lawn, Tampa Heights
Fall kicks off on the riverfront with a free local vendor market, live music, a petting zoo, pony and camel rides, face painting, and a bounce zone. The weekend also opens a free pumpkin patch that runs Thursday through Sunday for the rest of October.
View Event DetailsTaste of Latino Festival
Free12:00 to 6:00 PM · Centennial Park, 1800 E 8th Ave, Ybor City
Close out Hispanic Heritage Month at the 8th annual Taste of Latino Festival in historic Ybor City. This free, family-oriented celebration brings Latin food vendors, live cultural entertainment, and local businesses together in one afternoon.
View Event DetailsUpper Tampa Bay Oktoberfest
FamilyFri 5 to 10 PM, Sat 11 AM to 10 PM, Sun 11 AM to 6 PM · Tampa Bay Downs, 11225 Race Track Rd
The Upper Tampa Bay Chamber's annual Bavarian-themed weekend brings a kids' fun zone, car shows, challenge games, and wiener dog races to Tampa Bay Downs. Good times for the whole family, not just the beer garden crowd.
View Event DetailsFall Fest at Carrollwood Cultural Center
Free10:00 AM to 5:00 PM · Carrollwood Cultural Center, 4537 Lowell Rd, Tampa
Presented by the Carrollwood Village HOAs, this harvest-themed outdoor event brings live music, food trucks, artisan vendors, pumpkin painting, and bounce houses to the heart of Carrollwood.
View Event DetailsWesley Chapel Craft Festival
Family10:00 AM to 5:00 PM · The Shops at Wiregrass, 28211 Paseo Drive, Wesley Chapel
This dog-friendly weekend festival fills Wiregrass's main street with juried artists showing handmade jewelry, pottery, photography, and more. Free to attend, right in the heart of Wesley Chapel.
View Event DetailsShopapalooza Festival
Free10:00 AM to 5:00 PM · Vinoy Park, 701 Bayshore Dr NE, St. Petersburg
More than 350 local makers, small businesses, and food vendors set up along the St. Pete waterfront for one of the country's biggest Small Business Saturday celebrations. Free admission, a kids' zone with Santa photos, and a free trolley from the South Core Garage.
View Event DetailsLive Where You Love Tampa Bay
We have two homes available in the Tampa Bay market right now: 31848 Hedgerow Dr in Wesley Chapel's Fox Wood community, and 2209 Fletchers Point Cir in Carrollwood. Both are priced for today's buyer. We're bilingual and ready when you are.
Ocala Fall Events 2026
Headshots & Espresso Shots
A midday mixer in Ocala
Midtown Station, 235 NE Watula Ave, Ocala · Se habla español
Refresh your professional photo, fuel up on espresso and charcuterie, and meet professionals from across Ocala and Marion County. Co-hosted with Avera Visuals, GrowthHouse Digital, and Bellow Creative. Headshots are by reservation only and slots are limited, so save your spot and book a time.
McIntosh 1890s Festival
Family8:00 AM to 4:00 PM · Historic McIntosh, north Marion County
For 50 years, the little historic town of McIntosh has thrown this festival to help preserve its natural and historic charm. Expect around 280 arts, crafts, and antiques vendors under the oaks, and plan to arrive early: organizers expect about 25,000 visitors.
View Event DetailsEpic Eagles
Live Music7:00 PM · Circle Square Cultural Center, Ocala
North America's premier Eagles tribute band brings faithful renditions of "Hotel California," "Take It Easy," "Desperado," and more to Circle Square's intimate stage.
Get TicketsOcala Arts Festival (FAFO)
Free10:00 AM to 5:00 PM · Historic Downtown Ocala
Fine Arts for Ocala's 59th annual festival fills downtown with 150+ juried artists from across the country, plus live local music, student performances, a kids' art area, and food trucks. Admission is free and the festival is pet-friendly.
View Event DetailsOcala Food & Wine Festival
Food & WineWorld Equestrian Center, 1750 NW 80th Ave, Ocala
A three-day weekend of tastings, chef-driven dishes, and wine at the World Equestrian Center, one of Ocala's signature fall events. Ticketed; check the schedule for individual sessions.
View Event DetailsLight Up Ocala
Holiday3:00 to 8:00 PM · Downtown Ocala Square
Ocala's official holiday kickoff and lighting ceremony on the Downtown Square, a hometown tradition that brings families downtown to welcome the season.
View Event DetailsGainesville Fall Events 2026
The Great Pumpkin Bash
Family12:00 to 5:00 PM · Bo Diddley Plaza, Gainesville
Downtown Gainesville's second annual fall celebration brings a corn maze, pumpkin patch, games, face painting, a themed photo booth, and a pumpkin carving contest, all free to attend.
View Event DetailsMicanopy Fall Festival
FamilyHistoric Downtown Micanopy, just south of Gainesville
About 200 arts and crafts vendors and live music line Micanopy's historic main street under a canopy of live oaks. It's one of the most charming Old Florida weekends in Alachua County.
View Event DetailsDowntown Festival & Art Show
Free10:00 AM to 5:00 PM · Historic Downtown Gainesville
Now in its 45th year, this nationally recognized fine art festival transforms downtown Gainesville with 200+ juried artists, live music on multiple stages, and food, drawing tens of thousands of visitors each fall.
View Event DetailsLove What You See? Let’s Find Your Place in It.
Whether it's Tampa Bay, Ocala, or Gainesville, the Solara Real Estate Team knows these communities from the inside out. We're bilingual, local, and genuinely invested in helping you find the right home in the right neighborhood.
Join Us at Otoño a lo Cubano
Our free fall festival with a Cuban flair at Leto High School: Cuban food, music, dance classes, pumpkin painting, and local vendors for the whole family. ¡Te esperamos!