Things to do in Gainesville, FL: Fall 2025 - September -October

Fall in North Central Florida is a special time. The heat finally breaks, the football season is in full swing, and the calendar is jam-packed with festivals, concerts, and family-friendly celebrations. From Oktoberfest beers to bat conservation, here’s your ultimate guide to upcoming events in Gainesville, High Springs, and surrounding areas through the end of October.

🍺 Raise your stein — Gainesville’s favorite craft brewery is hosting its annual Oktoberfest celebration on September 26 at Swamp Head Brewery. Expect seasonal German lagers, hearty pretzels, and local food vendors serving up bratwursts and other Bavarian classics. Live oompah-style music keeps the festive energy flowing, while contests like stein-holding competitions and games give everyone a chance to participate.

Pro tip: bring a group of friends and claim your spot early — this event draws a big crowd of locals and visitors alike, eager to kick off fall with a toast.

🎨 If you prefer a night of art and culture, Artwalk Gainesville is also happening on September 26. Downtown galleries, boutiques, cafes, and even breweries transform into exhibit spaces showcasing local artists and makers. Stroll from venue to venue, meet the creators, and enjoy live music that spills into the streets.

Artwalk happens on the last Friday of every month, but September’s edition is extra lively with cooler weather making it perfect for a night out.

🎶 Just up the road in High Springs, the Gold Star Family Festival takes over from September 26–28. This three-day music festival honors Gold Star families (those who have lost loved ones in military service) with concerts, community activities, and memorial events. Expect country, rock, and acoustic sets, plus camping opportunities for those who want the full weekend experience.

It’s a meaningful way to enjoy live music while supporting veterans and their families.

🏈 SEC football fans, circle this one on your calendar: the Florida Gators face the Texas Longhorns at Ben Hill Griffin Stadium on October 4. This high-stakes matchup is one of the most anticipated games of the season, as Texas brings their powerhouse program to Gainesville.

With over 90,000 fans expected, “The Swamp” will be rocking with Gator chants, tailgating, and the Pride of the Sunshine marching band. Tickets are in high demand, so plan ahead — and don’t forget to book your lodging early. (Hint: short-term rentals like StayGainesville properties go fast during football weekends!)

🎃 Families looking for Halloween fun will love the Great Pumpkin Bash at Bo Diddley Plaza on October 11. This free, family-friendly event includes pumpkin carving, costume contests, live entertainment, and games for all ages.

Downtown Gainesville turns into a fall carnival, with food trucks and local vendors adding to the festive atmosphere. Bring the kids in costume and make a day of it.

🎸 Gainesville’s music scene takes center stage with FEST 2025, running October 24–26. This multi-day, multi-venue festival is one of the biggest punk rock gatherings in the country, bringing fans and bands from all over the world.

With dozens of venues hosting hundreds of performances, downtown Gainesville pulses with energy all weekend. Beyond the music, FEST has become a cultural phenomenon — expect food trucks, after-parties, and plenty of camaraderie among attendees.

If you’re planning to go, book accommodations ASAP — hotels and rentals sell out fast during FEST.

🦇 Celebrate one of Florida’s most fascinating species at the Florida Bat Festival on October 25. Hosted at the Lubee Bat Conservancy, the festival offers live bat encounters, educational talks, and opportunities to learn about conservation efforts.

Food trucks, craft beer, and local artisans add to the experience, making this event fun for all ages. It’s one of Gainesville’s most unique festivals, blending wildlife, science, and community spirit.

🌸 For garden lovers, the Fall Plant Sale & Orchid Show at Kanapaha Botanical Gardens is also on October 25. Walk the stunning garden trails while browsing vendors selling native plants, exotic orchids, and gardening supplies.

This event is a great way to add greenery to your home and learn from local horticulture experts. The orchids alone make it worth the trip — the exhibits showcase rare and vibrant varieties you won’t see anywhere else.

🚣 Gainesville’s rowing community shines during the Gatorhead Regatta on October 25 at Newnans Lake. Local, regional, and collegiate rowing teams compete in a day of races that highlight athleticism and team spirit.

Bring a blanket or chair, enjoy the lakeside views, and cheer on the athletes as boats glide across the water. It’s an underrated but exciting part of Gainesville’s fall calendar.

🎶 Every Friday night in October, the Free Fridays Concert Series lights up Bo Diddley Plaza with live music. Local and regional bands cover genres from blues and jazz to rock and reggae.

Grab a bite from downtown restaurants or food trucks, bring a lawn chair, and enjoy Gainesville’s longest-running outdoor concert tradition.

🌽 Looking for classic fall fun? Head to Crossroads Farm Fall Festival & Corn Maze. All month long, visitors can enjoy hayrides, pumpkin patches, photo ops, and, of course, the corn maze challenge.

It’s a perfect outing for families, couples, or friend groups who want to embrace the season’s charm.

🎉 Nothing screams school spirit like UF Homecoming Weekend. Expect a massive parade, pep rally, and Gator Growl, the student-run entertainment showcase featuring comedians, live music, and fireworks.

Alumni, students, and families pack Gainesville for this tradition, making it one of the biggest weekends of the year. Don’t be surprised if searches for “UF Homecoming hotels” spike — it’s one of the hardest weekends to find lodging.

From craft beer festivals to college football showdowns, Gainesville and High Springs are buzzing with activity this fall. Whether you’re an alum returning for Homecoming, a family looking for pumpkin patches, or a music lover ready for FEST, there’s something for everyone.

💡 Pro Tip: Book your lodging early! Gainesville hotels and rentals sell out quickly during football weekends, festivals, and major events. StayGainesville offers fully furnished vacation rentals with the comfort and convenience you need to make the most of your trip.