The Top 10 Things To Do in Orlando this Weekend, May 29 - 31, 2026
- Emma Walton
- 42 minutes ago
- 4 min read
The weekend has arrived, and with so much to enjoy, we've brought together the ten best things to do in Orlando throughout the weekend that you can't afford to miss!
Looking for something fun to do in Orlando this weekend? The good news is that there is a huge variety of exciting happening around the city, including live music, stand-up comedy shows, car shows, sporting events, musicals, plays, nightlife, food and drink experiences and so much more.
With so much to do this weekend in Orlando and throughout Central Florida, we've selected the top 10 events and things to do that we consider a must-do, events that you can't afford to miss, and that will make your weekend memorable!
Top 10 Things To Do In Orlando This Weekend, May 29 - 31, 2026
May 29 - 31
Get ready for a far-out weekend, Celebration. Can you believe it? We've been making good beer and sharing good vibes for TWO whole years right here in Celebration, Florida. Time flies when you're brewing up a storm, and now it’s time to Keep on Celebratin’! We are pulling out all the stops for our biggest party yet—a massive, three-day retro-groovy anniversary bash. Dust off your bell-bottoms, grab your flower crowns, and join us for a weekend packed with nostalgic fun and great craft beer.
May 29 - 30
Banana Ball is coming to ESPN Wide World of Sports Complex at Disney World for the first time ever, as the Loco Beach Coconuts take on the Party Animals.
May 29 - 31
Spooky Empire has been delivering the best sights, sounds and screams to Halloween lovers since 2003. Taking place in the DoubleTree by Hilton Orlando Theme Park Resort, Spooky Empire features an enormous room of vendors, a film and tattoo festival, music, celebrities, and more to satiate even the most diehard aficionados of the spooky season!
May 29
Get ready to kick off summer the sweetest way possible in Downtown DeLand! Perfectly timed to celebrate the last day of school. Stroll through downtown as you sample delicious ice cream from local favorites, one stop at a time.
May 29
9x diamond-certified global superstar Post Malone and 3x GRAMMY award-winning entertainer Jelly Roll are set to return to the road with Post Malone and Jelly Roll Present: The BIG ASS Stadium Tour Part 2, continuing the momentum of their record-breaking stadium run. The tour includes a show in Tampa, with Post Malone and Jelly Roll Present: The BIG ASS Stadium Tour Part 2 hitting Raymond James Stadium on May 29.
May 30 - 31
Get ready for Gatorland’s 7th Annual Gatorpalooza! This action-packed festival is full of family fun, exciting entertainment, and, of course, all the alligators, animals, and awesomeness that make Gatorland “The Alligator Capital of the World!” Live DJ & Music, Specialty Food Vendors, Artisans & Craft Vendors, Games & Family Fun, Meet the Gatorland Vlog Team Live! PLUS, don’t miss the – 6th Annual Gatorland Florida Man Challenge on Saturday, May 30 – a wild and wacky competition like no other!
May 30
PrideFest Kissimmee is a vibrant celebration dedicated to honoring and embracing the rich diversity and impactful contributions of our local LGBTQIA+ community. As we come together in unity, this event serves as a beacon of inclusivity, fostering awareness and understanding while showcasing the talents and achievements of our LGBTQIA+ neighbors. Join us for a day filled with live performances, engaging activities, and diverse vendors, as we celebrate love, acceptance, and pride in the heart of Kissimmee.
May 30
Enjoy everything you love about the Science Center – without the kids! Special programming is designed just for adults. There’s no age limit on curiosity, and whether you're looking for a get-together of old friends or a fun date night out, Science Night Live is your chance to let out your inner child and experience the joy of science! Explore interactive exhibit halls, try hands-on experiments in Dr. Dare's Lab, and catch special guest speakers.
May 31
Celebrate 10 years of creativity, community, and culture at Milk Mart’s 10th Anniversary Festival in Orlando! This beloved local event brings together hundreds of artists, makers, food vendors, and musicians for one unforgettable day of shopping, eating, and exploring.
May 31
This spectacular spring performance from Orlando Gay Chorus at Steinmetz Hall promises to inspire, uplift, and delight—reminding us all that even in the most challenging times, our community’s music remains louder than fear, stronger than hate, and filled with unstoppable pride.
What are you most excited for this weekend? Let us know in the comments, and visit https://www.gottagoorlando.com/weekend-guide for a complete list of happenings!
For a complete guide to everything happening in Orlando this month, check out The Best Things To Do In Orlando This Month.
Before attending any of the events listed on Gotta Go Orlando, you should contact the organizer or venue to confirm that the event is taking place as information, changes, and cancellations can and do occur.
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