What’s Happening Around Central Florida This September?

By: The Clearvue Insurance Team 

Whether you’re soaking up the last days of summer or getting excited for fall, Central Florida has something fun in store. From farmers markets to food truck festivals and fishing history, here are a few local events worth adding to your calendar.

📍 Winter Haven – Saturday Farmers Market
🗓 Every Saturday in September 
Explore downtown Winter Haven with local produce, handmade goods, and a welcoming community vibe. Great for a slow Saturday morning stroll or quick grocery run with flair. 
🔗 visitcentralflorida.org/events/winter-haven-farmers-market/


📍 Clermont – First Friday Food Trucks
🗓 Friday, September 5
Head to downtown Clermont for a lively evening filled with food trucks, live music, and community spirit. Bring the family—or a date—and try something new! 
🔗 www.clermontdowntown.com/first-friday-clermont

📍 Clermont – Sunday Farmers Market
🗓 Every Sunday in September 
Discover locally grown produce, baked goods, and artisan crafts in historic downtown Clermont. A great way to kick off your week. 
🔗 www.clermontdowntown.com/farmers-market


📍 Clermont – Anime Night Market
🗓 Saturday, September 20 | 4 PM – 8 PM 
Downtown Clermont transforms into a pop-culture playground with cosplay, themed vendors, food, and entertainment along 8th Street (between Montrose & Minneola). 
🔗 www.clermontdowntown.com/events/anime-night


📍 Lakeland – First Friday Downtown (“Septoberfest”)
🗓 Friday, September 5
Enjoy live music, art displays, food trucks, and themed vendors in a fun, block-party atmosphere. 
🔗 downtownlkld.com/feature1/septober-fest-first-friday-september-5/


📍 Lakeland – Lakeland Flying Tigers Baseball
🗓 Early September (check schedule) 
Catch a minor league game before the season ends at Publix Field at Joker Marchant Stadium. Affordable fun for the whole family. 
🔗  www.milb.com/lakeland/schedule/2025-08


📍 Orlando – U.S. Air Force Brass Quintet at Lake Eola
🗓 Friday, September 19 | 07:00 PM to 09:00 PM
Enjoy a free outdoor performance by the U.S. Air Force Band of the West’s Brass Quintet in beautiful Lake Eola Park. 
🔗 www.orlando.gov/Events/U.S.-Air-Force-Band-of-The-West-Brass-Quintet


📍 Orlando – Finally Food Truck Friday (Season Finale)
🗓 Friday, September 26 
Celebrate the last Food Truck Friday of the season with great eats and good vibes in the Milk District. 
🔗 www.orlando.gov/Events/Finally-Food-Truck-Friday-September-2025

📍 Tampa – “Lure of Florida Fishing” Exhibit
🗓 Now through January 2026 
📍 Tampa Bay History Center 
This new exhibit explores Florida’s rich fishing history with vintage tackle, rare photos, and historic artifacts. A great rainy-day plan for families or curious minds. 
🔗 tampabayhistorycenter.org/event/the-lure-of-florida-fishing/

📍 Eustis – Fall at Amber Brooke Farms
🗓 Weekends from September 21 – November 3 
Welcome fall early with sunflowers, pumpkins, food vendors, cow trains, and u-pick flower fields. It’s the kind of place kids will love and Instagram will thank you for. 
🔗 amberbrookefarms.com/5th-annual-fall-festival/

📍 Tampa – Anime St. Pete
🗓 September 14–15 
📍 The Coliseum, St. Petersburg 
Anime fans, this one’s for you! Celebrate your favorite shows, meet voice actors, browse artist alley, and show off your best cosplay. Perfect for kids, teens, and nostalgic adults. 
🔗 animestpete.floridacomiccons.com/

📝 Local Tip: Always check the official event websites for admission details, parking tips, and weather updates—especially for outdoor events. 

🍂 Whether you're looking for a family day out, a casual weekend date, or something different to do, these September events are full of local flavor and fall fun. 

Wishing you a warm and adventurous start to the season from all of us at Clearvue Insurance!