10 Fun Things to Do in Orlando This Weekend (May 29–31, 2026)
Summer break is officially here and the kids are already looking for things to do. If you’re trying to figure out how to fill the weekend, there are some really cool local events popping up around town. From giant food truck markets to a festival at Gatorland, here are 10 great ways to get out of the house.
1. Milk Mart 10th Anniversary Birthday Bash
This favorite local market is celebrating ten years with an outdoor birthday bash in the heart of The Milk District. Grab the kids, walk the stroller around to check out the local vendors, and make sure to grab lunch from one of the food trucks while you’re there.
- Date: Sunday, May 31, 2026
- Location: The Milk District Pavilion & Grounds, 2428 E Robinson St, Orlando, FL 32803
- Cost: FREE admission
- Link: milkmartorlando.com
2. Spooky Empire Horror & Sci-Fi Convention
If you have teenagers or pop-culture fans at home, this giant fan convention is back in town for the weekend. It features celebrity guests, local artists, and some pretty incredible costume contests that are a lot of fun to see in person.
- Date: Friday, May 29 – Sunday, May 31, 2026
- Location: DoubleTree by Hilton Hotel at the Entrance to Universal Orlando, 5780 Major Blvd, Orlando, FL 32819
- Cost: Ticket prices vary by single-day or weekend pass
- Link: spookyempire.com
3. “Weird Al” Yankovic: Bigger & Weirder Tour
Take the family out to the arena for a night of pure musical comedy as “Weird Al” brings his summer stadium tour to town. It’s a high-energy, clean show full of his classic song parodies that will keep both you and the kids laughing the whole time.
- Date: Friday, May 29, 2026; 8:00 PM
- Location: Kia Center, 400 W Church St, Orlando, FL 32801
- Cost: Ticket prices vary by tier seating
- Link: kiacenter.com
4. Florida Stationery Fest
This three-day creative setup is a great afternoon stop if anyone in your house loves notebooks, pens, stickers, or paper crafts. You can browse tons of unique supplies from independent makers and even jump into a few hands-on crafting workshops.
- Date: Friday, May 29 – Sunday, May 31, 2026
- Location: The Florida Hotel and Conference Center, 1500 Sand Lake Road, Orlando, FL 32809
- Cost: Ticket pricing options vary by session
- Link: floridastationeryfest.com
5. Formula Drift at Orlando Speed World
Perfect for older kids, gamers, or anyone in the family who loves fast cars. Grab some ear protection for the little ones and watch top drivers from all over the world slide high-horsepower cars through tight curves.
- Date: Friday, May 29 & Saturday, May 30, 2026
- Location: Orlando Speed World Dragway, 19164 E Colonial Dr, Orlando, FL 32820
- Cost: Ticket prices vary by single-day or weekend pass
- Link: formulad.com
6. Wawa Summer Fun Days at Bok Tower Gardens
Skip the busy theme park crowds and spend a relaxed morning exploring the shaded garden paths out by the singing tower. Wawa is hosting their summer fun days, meaning it’s a great time to let the kids burn off some energy at the Hammock Hollow nature play area.
- Date: Friday, May 29, 2026
- Location: Bok Tower Gardens, 1151 Tower Blvd, Lake Wales, FL 33853
- Cost: Regular admission fees apply
- Link: boktowergardens.org
7. Gatorpalooza Weekend & The Florida Man Challenge
Gatorland is hosting its annual weekend festival with a live DJ, local food trucks, artisan crafts, and access to their built-in splash pad. If you go on Saturday, you can also catch their hilariously unique “Florida Man Challenge” competition.
- Date: Saturday, May 30 & Sunday, May 31, 2026 (Florida Man Challenge takes place Saturday)
- Location: Gatorland, 14501 S Orange Blossom Trail, Orlando, FL 32837
- Cost: Included with regular park admission
- Link: gatorland.com
8. Florida Wildlife Corridor Film Screening & Conservation Panel
If you’re looking for an easy, educational indoor activity, check out this double-feature film screening focused on local wildlife. It’s a great way for older kids and teens to learn about Florida’s native ecosystems and chat with local conservation experts.
- Date: Friday, May 29, 2026
- Location: Central Florida Conservation & Event Venues (Check host page for updates)
- Cost: Admission varies by venue session
- Link: visitcentralflorida.org
9. Orlando Pride vs. Bay FC Match
Throw on your purple gear and head down to Inter&Co Stadium to cheer on our local professional women’s soccer team. It’s a fast-paced, high-energy game that makes for a perfect outdoor family night right in downtown Orlando.
- Date: Friday, May 29, 2026; Match kicks off at 7:00 PM
- Location: Inter&Co Stadium, 655 W Church St, Orlando, FL 32805
- Cost: Ticket prices vary by section
- Link: orlandocitysc.com/pride
10. Repticon Orlando at the Central Florida Fairgrounds
If you have animal lovers or curious kids in the house, this massive reptile and exotic pet market is a really fun stop. Breeders and educators from all over the region will be there, making it a safe place for kids to see unique creatures up close.
- Date: Saturday, May 30 & Sunday, May 31, 2026
- Location: Central Florida Fairgrounds, 4603 W Colonial Dr, Orlando, FL 32808
- Cost: Ticket prices vary by single-day or weekend pass
- Link: centralfloridafair.com
