There’s something about Jacksonville that always makes me feel like the city is alive in rhythm with the seasons. It’s not just the ocean breeze or the St. Johns River winding through downtown—it’s the way the community gathers, celebrates, and fills the calendar with festivals, concerts, and outdoor events that bring the city to life. When I first started planning longer visits to Jacksonville, I realized the best way to understand the city wasn’t only through its neighborhoods or its beaches—it was by following its festival calendar, especially in September, when summer slowly folds into autumn and the city becomes one big outdoor stage.
In this story, I’ll walk you through Jacksonville’s festival and event calendar, share what it’s like to actually be there, and give you practical tips so you don’t miss out. I’ll focus on September but will weave in highlights from other months to give you the full picture.
The Pulse of Jacksonville in September
September in Jacksonville has its own pulse. The days are still warm—sometimes hot—and the evenings carry that sticky Southern humidity, but it’s balanced by breezes that roll in from the Atlantic. For me, September has always been about energy and creativity.
I remember one September evening, standing on the Jacksonville Riverwalk with music in the distance, food trucks lining the promenade, and crowds spilling into every corner of the street festival. It was my first taste of how September serves as the unofficial kick-off to Jacksonville’s “cultural season.”
So, what exactly fills the calendar? Here are some of the city’s most notable September events, alongside tips I’ve gathered from attending them.
1. Jacksonville Jazz Festival
When I think of Jacksonville in September, the Jacksonville Jazz Festival immediately comes to mind. Though it occasionally shifts to October in some years, many of the city’s pre-festival activities and smaller jazz showcases bloom in September. For anyone who loves live music—or simply enjoys being swept into the current of a city at its most vibrant—this festival is a must.
Walking into the festival felt like walking into a dream: streets blocked off, stages set up against the backdrop of skyscrapers, and music flowing into the humid night air. The notes of saxophones blended with the chatter of crowds, the aroma of barbecue and seafood wafting from food stalls. I sat down on the curb with a plate of shrimp tacos from a local food truck and listened to an up-and-coming quartet whose energy was infectious. I didn’t even know their names, but the way the drummer smiled at the bassist while improvising told me this was the kind of spontaneous magic jazz is all about.
The diversity of the lineup is one of the most exciting parts—there are Grammy-winning headliners on the main stage and local bands tucked into side streets, each creating a completely different atmosphere. At one point, I wandered into a smaller crowd gathered around a group of students from a local music school. Their performance wasn’t on the official program, but people stopped, clapped along, and even started dancing in the street. That moment captured the festival’s spirit: inclusive, joyful, and unpretentious.
What surprised me most was how family-friendly it all felt. Kids danced in front of the stage, grandparents sat in foldable chairs tapping their feet, and groups of friends sprawled out on picnic blankets. I didn’t feel the chaos that sometimes comes with big city festivals—it felt communal, like the whole downtown had turned into one big living room.
Practical Tips:
- Bring a light folding chair or blanket; seating fills quickly and being comfortable makes the long sets much more enjoyable.
- Pack a reusable water bottle—the Florida sun doesn’t joke, and hydration is key if you’re spending hours outside.
- Don’t be afraid to wander between stages; some of the most magical performances are from lesser-known musicians.
- Try to arrive just before sunset—the golden light against the skyscrapers and the first notes of evening sets is unforgettable.
Costs & Booking: The Jazz Festival is usually free, which makes it accessible to everyone, but there are VIP passes that can be purchased through sites like Eventbrite or the festival’s official website. VIP access can range from \$60 to \$200, depending on perks like reserved seating or backstage entry. If you’re someone who loves being close to the stage or avoiding the hassle of finding a spot, VIP is worth considering.
I usually check Hotels.com or Booking.com for nearby hotel deals since downtown accommodations can book out fast that weekend. Once, I booked a room at the Hyatt Regency along the river, and being able to walk out of the lobby straight into the festival was priceless. Staying within walking distance saves the hassle of parking and makes it easier to come and go during the day.
2. Jacksonville Taco & Tequila Festival
Another September highlight is the Taco & Tequila Festival, hosted in Riverside’s Riverside Park. I’ll admit, food festivals are my weakness, but this one is on another level. Imagine rows of tents under sprawling oak trees, each vendor dishing out tacos that range from the traditional to the completely unexpected. The first time I went, I tasted brisket tacos smothered in smoky salsa, shrimp tacos topped with tropical slaw, and even vegan jackfruit creations that fooled my taste buds into thinking they were pulled pork. Every stall seemed to put a twist on something I thought I knew.
What made it unforgettable was the pairing: tequila cocktails, from classic margaritas to inventive blends with watermelon, jalapeño, or hibiscus. I’m not usually a tequila person, but sipping a hibiscus margarita while sitting on the grass and listening to live Latin music changed my mind. The festival does a great job of creating spaces where you can not only eat and drink but also linger—there are picnic areas, small stages with DJs or live bands, and art vendors selling handmade crafts.
One of the highlights for me was chatting with the chefs themselves. At one booth, a local restaurateur explained how his grandmother’s recipes inspired his spicy carne asada marinade. At another, a young food truck owner talked about experimenting with fusion tacos, blending Korean flavors with Southern barbecue. That level of personal connection made every bite feel like a story.
Tips for First-Timers:
- Go early; lines for the best vendors form quickly, and tacos can sell out.
- Bring cash; though most accept cards, some smaller vendors move faster with cash transactions, and you’ll appreciate skipping the wait.
- Use rideshare apps or stay nearby—after a tequila tasting, driving is off the table.
- Pace yourself. With so many options, it’s easy to fill up too fast. Sharing tacos with friends is the best way to sample more variety.
- Costs: Entry tickets are generally \$15–\$30, which can be booked through Eventbrite or the festival’s site. Food and drinks are purchased separately, and I usually budget around \$40–\$50 extra to really indulge without worrying about prices at each booth. Compared to a night out at a restaurant, the value is fantastic because you get not only the food and drinks but also live entertainment and a festive atmosphere.
- By the end of the day, I was full, sun-kissed, and carrying a small bag of artisan hot sauces I couldn’t resist buying from a vendor. Walking out of Riverside Park with music still echoing in the distance, I felt that rare combination of satisfaction and discovery—you go in for tacos but leave with a deeper appreciation of Jacksonville’s creativity and community spirit.
3. Art Walk in Downtown Jacksonville
The Jacksonville Art Walk happens on the first Wednesday of every month, which means you’ll always catch one in September. Picture this: downtown streets transformed into an open-air gallery, with artists painting live, musicians busking on corners, and food trucks lining the edges.
My favorite memory is stumbling upon a chalk artist near Hemming Park—the detail in the portrait she was creating on the sidewalk was astonishing. I stayed longer than I planned, watching layer by layer come alive, while a saxophonist played nearby.
Tips:
- Wear comfortable shoes—you’ll wander more than you expect.
- Stop at local restaurants along the way; I once ducked into a café on Bay Street for iced coffee and ended up chatting with the barista about her favorite hidden murals in the city.
- Arrive before sunset to see both the art in daylight and under the glow of streetlights.
Costs: Free to attend, though I always set aside a budget for supporting local artists (many sell prints or small crafts for \$10–\$20).
4. Jax River Jams
Though sometimes scheduled earlier in the year, Jax River Jams often extends or overlaps into September with community concerts. These open-air shows by the river are pure Jacksonville: lively, scenic, and communal.
One night I remember leaning against the railing of the Riverwalk, a local indie band playing while the skyline reflected on the water. Food trucks were lined up nearby, and kids danced barefoot on the grass. That moment, with music, river breeze, and the buzz of community all colliding, perfectly encapsulated Jacksonville for me.
Tips:
- Bring bug spray—the river attracts mosquitoes.
- Arrive early to claim a good spot on the lawn.
- Parking near the Riverwalk fills up quickly, so rideshare or walking from a downtown hotel is easier.
5. College Football Kickoff Events
September also means college football season—and in Jacksonville, that comes with tailgates, pep rallies, and watch parties. Even if you’re not a diehard football fan, the energy is contagious. I joined a tailgate near TIAA Bank Field, and the sheer camaraderie—grills smoking, fans tossing footballs, music blasting—was unforgettable.
Tips:
- Wear team colors, even if you don’t have a favorite—you’ll fit right in.
- Be ready for heavy traffic around stadium events.
- Hydrate—daytime tailgates in Florida heat can be intense.
Beyond September: Year-Round Highlights
Though September is special, Jacksonville’s calendar stretches across the year:
- Springing the Blues Festival (April): A massive blues event at Jacksonville Beach.
- Jacksonville Light Boat Parade (November): Boats decorated with holiday lights float down the river.
- Jacksonville Film Festival (Summer): Screenings of indie and international films.
I’ve learned that checking the Visit Jacksonville website or browsing events on Eventbrite is the best way to keep track.
Booking Flights & Accommodation for Events
If you’re traveling into Jacksonville for September festivals, flights to Jacksonville International Airport (JAX) are frequent. I often use:
- Google Flights to compare dates and prices.
- Expedia for package deals (flight + hotel).
- Skyscanner for flexible date searches.
Hotels near downtown or Riverside make walking to events easy. I’ve booked through Booking.com, Hotels.com, and sometimes directly via Marriott or Hilton for loyalty rewards. For longer stays, I recommend looking at Airbnb or Vrbo—both platforms often have lofts near the Riverwalk.
For food, I lean on OpenTable for restaurant reservations and Resy for trendier spots that fill up during festival weekends.
Traveler Notes & Final Advice
- Pack light but smart—comfortable shoes, sunscreen, and a small portable fan for humid evenings.
- Check event websites—dates can shift year to year.
- Support local vendors—buy art, taste local food, tip street performers.
- Budget flexibility—while many festivals are free, food, drinks, and special passes add up.
- Travel insurance—if you’re flying in for a specific festival, consider coverage for delays or cancellations.
For me, Jacksonville’s September calendar isn’t just about events—it’s about the way the city brings people together. From the jazz notes drifting across downtown streets to the taste of a handmade taco paired with a bold tequila, these experiences stitched together create a living, breathing portrait of Jacksonville.
