September is a great time to experience Orlando beyond the theme parks. As summer winds down, the city comes alive with live music, outdoor movies, food festivals, pet-friendly events, and plenty of opportunities to enjoy the cooler-season spirit. Whether you’re visiting with family, traveling with your four-legged friend, or simply looking for something different to do, these September events in Orlando offer something for everyone.
Labor Day Jazz Festival With Eric Alexander
September 7, 2026
Photo courtesy of Timucua Arts Festival
Kick off September with an afternoon and evening of live jazz at Timucua’s Labor Day Jazz Festival. Taking place at The White House in Orlando, this special event brings the Chicago Labor Day Jazz Festival tradition to Central Florida. The September 7 celebration runs from 3–10:30 p.m. and features four bands, including a quartet featuring award-winning saxophonist Eric Alexander.
Your $50 ticket includes access to a Labor Day cookout and beer, followed by performances throughout the evening. With music beginning at 4 p.m. and additional shows at 5, 6, 7, and 8 p.m., it’s a fun way for jazz fans to spend the holiday.
Popcorn Flicks in the Park: Shrek 2
September 10, 2026
Photo courtesy of Enzian Theater
Grab a blanket and head to Central Park in Winter Park for a free outdoor movie night featuring the beloved animated comedy Shrek 2. The film will be shown Thursday, September 10, at 8 p.m. as part of Enzian’s Popcorn Flicks in the Park series, presented in partnership with the City of Winter Park.
The monthly series is free and open to the public, making it an easy addition to an Orlando vacation itinerary. Bring the family, settle in under the stars, and enjoy a nostalgic favorite with Shrek, Fiona, Donkey, and Puss in Boots.
Dessert Wars Orlando
September 19, 2026
Photo courtesy of Dessert Wars
If you have a sweet tooth, don’t miss Dessert Wars Orlando on Saturday, September 19, from 3–6 p.m. at the Central Florida Fairgrounds. Billed as America’s largest dessert festival, the event brings together dessert vendors competing for the title of Dessert Champion.
Visitors can sample an impressive selection of sweet treats, from cupcakes and cookies to ice cream and doughnuts. With the event known to sell out, dessert lovers should consider purchasing tickets in advance.
Drinks Along the Drive
September 19, 2026
Photo courtesy of College Park
Spend an afternoon exploring Orlando’s College Park neighborhood during Drinks Along the Drive. Taking place from 3–6 p.m. on Saturday, September 19, the event transforms Edgewater Drive into a tasting experience featuring participating local businesses.
Guests can sample featured wines, beers, and seltzers while discovering small businesses along the popular neighborhood corridor. The afternoon also includes live music from Hannah Stokes and a Collective Corner Pop-Up Market at Albert Park. Tickets are $25, limited, and must be purchased in advance.
Pets on the Promenade: Fall Edition
September 20, 2026
Photo courtesy of The Promenade
Bring your furry family member along for a fall afternoon at Pets on the Promenade at Sunset Walk on Sunday, September 20, from 12–4 p.m. This free, pet-friendly event features live music, street performers, pet-focused activities, and specials at participating restaurants and businesses.
Admission and parking are free, and all pets must be leashed. With plenty of restaurants, shops, and entertainment options surrounding the event, it’s a fun way to enjoy a day out with your best friend.
Oktoberfest Weekend
September 24–27, 2026
Photo courtesy of Lake Nona
Get ready to say “Prost!” at Boxi Park Lake Nona during Oktoberfest Weekend, taking place September 24–27. The celebration combines Bavarian-inspired fun with Boxi Park’s signature outdoor atmosphere, live entertainment, food, and drinks.
The weekend lineup includes a Thursday run club, a Friday keg tapping, and Saturday activities such as a best-dressed costume contest, pretzel ring toss, and human wheelbarrow race. It’s a lively way to wrap up September with friends and family.
Make the Most of September in Orlando
From live jazz and outdoor movies to indulgent desserts, neighborhood tastings, pet-friendly fun, and Oktoberfest celebrations, September offers plenty of ways to experience a different side of Orlando. Add a few of these events to your itinerary, then make the most of your vacation by returning to a comfortable resort where you can relax and recharge after a day of exploring.