We’re cruising into September. | Photo via Orlando Boat Show
Take out your calendar, grab your planner, or text all your friends — you just found ORLtoday’s Plan Ahead. This list features some of the biggest events taking place throughout Orlando this September.
(Don’t see anything you like? Check out our full events calendar.)
Orlando Boat Show | Friday, Sept. 5-Sunday, Sept. 7 | Times vary | Orange County Convention Center | $10 | Set sail as 21 of Central Florida’s top boat dealers showcase over 500 different boats from 80+ manufacturers.
Winter Parktoberfest | Saturday, Sept. 6 | 4-10 p.m. | Mead Botanical Garden, Winter Park | $29+ | Raise a stein and celebrate with beer, German food, entertainment, and a Dachshund Dash — first drink included with ticket.
Benson Boone | Tuesday, Sept. 16 | 8 p.m. | Kia Center, Orlando | $84+ | Don’t flip out, Benson Boone will do that during his “American Heart World Tour.”
Orlando Pride vs. Bay FC | Saturday, Sept. 13 | 5 p.m. | Inter&Co Stadium, Orlando | $20+ | The local team hosts its first-ever teddy bear toss to benefit Orlando Health Arnold Palmer Hospital for Children.
Finally Food Truck Friday | 5-9 p.m. | Lake Eola Park International Plaza | Free | Find your new favorite spot to eat at this night of food trucks and tunes.
Orlando Pride vs. Gotham FC | 8 p.m. | Inter&Co Stadium | $20+ | Cheer for the Pride on “Around The World In 90 Minutes” night, an international celebration of culture presented by Disney.
Saturday, Aug. 30
The Happiest Market: The Happiest Story | 12-5 p.m. | Dezerland Park | Free | Celebrate this magic-inspired market’s first anniversary with 80+ vendors, photo ops, refreshments, and more fun.
When We Were Punk ’25 | 6:30 p.m. | House of Blues, Lake Buena Vista | $21 | Relive your pop-punk days with Blink-180 Deux, The Chili Poppers, and The American Idiots paying tribute to blink-182, the Red Hot Chili Peppers, and Green Day.
Sharks in the Water: The Big Za Bash | 8 p.m. | Addition Financial Arena | $84+ | Turn up and celebrate BossMan Dlow at this show that features performances by artists like Glorilla, Sexyy Red + 42 Dugg.
Sunday, Aug. 31
Wu-Tang Brunch | 12 p.m. | Catrinas Mexican Fusion | $37 | We hope you take your coffee with “C.R.E.A.M.” — dig into a brunch as you listen to tunes from Wu-Tang Clan members and the golden age of rap.
Kem | 8 p.m. | Hard Rock Cafe | $118+ | Groove into the night as the soul and R&B singer performs.
Love spooky season? New Bern is famous for its spine-tingling guided ghost walks + haunted houses. | Photos courtesy Visit New Bern
Eyeing somewhere a little cooler + more colorful for your autumn escape?
Round-trip flights from Orlando to New Bern, NC start under $60 this fall — giving you the chance to snuggle up in your fave sweater and watch red and yellow leaves transform the landscape.
Explore walkable streets in the delightful downtown, relax at boutique stays with waterfront views, and enjoy the lively food + art scene in North Carolina’s first capital (and the birthplace of Pepsi-Cola).
Siemens Energy is charging forward with plans to move to Lake Nona Town Center. The German energy corporation signed a lease to take over nearly 243,000 sqft of office space — Orlando’s largest office lease in a decade. The company plans to move into the Marwick Lane space in 2027. (CoStar)
Coming Soon
Orlando-based grocer Freshfields Farm plans to open a fresh store in Apopka — its second Orange County location and third overall. The new store will be at a 5.58-acre site on Piedmont Wekiva Road and is expected to open in the first quarter of 2027. (Orlando Business Journal)
Closing
Mall boutique Claire’s has announced plans to close 235 stores nationwide, and one local retail space is an accessory to this decision. The company listed the Waterford Lakes Town Center store as one of the locations slated to shutter, but a closing timeline has not been announced. (USA TODAY)
Seasonal
Halloween Horror Nights begin tomorrow at Universal Studios Florida, but there’s a new way to enjoy the excitement without as many scares. The attraction will sell a “Deathly Afraid” necklace for $20, alerting actors to take their startling antics elsewhere. (Attractions Magazine)
Real Estate
Homesellers in Orlando have been waiting longer to make sales. According to data from Realtor.com, the average house has been sitting on the market for 16 days longer than it did a year ago, one of the signs that the local real estate market is cooling.
List
Superica has raised the bar-rito. The Winter Park restaurant was ranked as the No. 1 Mexican restaurant in the Orlando area, based on Yelp data compiled by Stacker. Don’t worry if you prefer a different spot, the list also includes 10 more local restaurants.
Tell your mateys, The Beak and Barrel is here. Today, Aug. 29, is the day Walt Disney World’s new pirate-themed lounge opens inside Adventureland at Magic Kingdom Park — the park’s first-ever dedicated lounge.
The pub draws inspiration from the “Pirates of the Caribbean” franchise, which can also be seen on the menu. It features Caribbean-influenced dishes, cocktails, mocktails, beer + wine. And, in true Jack Sparrow fashion, the lounge also features a selection of rum pours.
If you want to get inside, you will need to make a reservation, but be forewarned. Availability may be limited due to the popularity of the new attraction.
The fun doesn’t have to end here. After reading the newsletter, head over to our games page. Games refresh with new challenges every day at 6 a.m. from crossword puzzle to Sudoku to themed word search.
It’s hard to believe, but by the end of the weekend, it will be September. This gives you a few days to complete any goals you had for the month of August.
Personally, I wanted to fill my empty flower pots with new plants to spruce up my indoor space. Perhaps I’ll take a trip to City Oasis this weekend.
