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Orlando’s Best Labor Day Weekend Events for Families

Labor Day weekend in Orlando is the ultimate way to say goodbye to summer. With theme parks galore and plenty of family-friendly activities and events, Orlando is the ideal place to spend the long holiday weekend. Check out these family-friendly Labor Day Weekend events during your visit:

Orlando Labor Day Weekend Events

  1. Orlando Magical Dining Month
  2. Promenade at Sunset Walk Labor Day Weekend Celebration
  3. Annual Labor Day 5K
  4. Family Fun Day at Boxi Park
  5. Free Admission to Harry P Leu Gardens
  6. Visit the Theme Parks 

1. Orlando Magical Dining Month: August 15 – September 30, 2025

Dine your way around Orlando during the 20th Annual Orlando Magical Dining Month! With over 160 restaurants in Orlando participating, it’s the perfect time to experience what the Orlando culinary scene has to offer. From August 15th to September 30th, participating restaurants will offer a prix-fixe menu ranging from $40 – $60. The three-course dinner includes the choice of an appetizer, entree, and dessert from the restaurant’s Visit Orlando’s Magical Dining menu (tax, gratuity, and tip are not included). Feast on fresh seafood, juicy steak, and more during Orlando Magical Dining Month.

2. Labor Day Weekend Celebration: August 29 – September 1, 2025

Car Show Labor Day Weekend Orlando

Celebrate the unofficial end of summer with Promenade Sunset Walk at their Labor Day Weekend Celebration! It will be four fun-packed days of live music, entertainment, bands, DJs, and street performers. Shop for handcrafted goods at the artisan market, grab a bite from delicious food vendors, or attend Friday night’s racing car and truck show! There is something for everyone in the family.

3. Annual Labor Day 5K: August 31, 2025

Celebrate Labor Day with a run on one of Orlando’s most beautiful courses! The 6th Annual Labor Day 5K takes runners around Lake Baldwin, where you’ll get plenty of beautiful water views and shade as you traverse the course. The start and finish will be at Harbor Park, and all participants will receive a performance race shirt, a finisher medal, snacks, drinks, and a swag bag filled with donated items from sponsors. Registration is $40 for adults and $20 flat fee for children 17 and under. 

4. Family Fun Day at Boxi Park: August 31, 2025 

Join in on Family Fun Day at Boxi Park, Labor Day weekend, for a day filled with fun, family-friendly activities. The event starts at 1:00 PM with live music, face painting, and a balloon artist. Live music will run until 7:00 PM, and there will be plenty of other activities and food for all to enjoy! The event is FREE to attend.

5. Free Admission to Harry P Leu Gardens: September 1, 2025

Take advantage of Harry P Leu Gardens’ free admission day! The gardens are open to the public free of charge on Labor Day, thanks to sponsors Orlando Health and Massey Services Inc. Check out the popular Origami in the Garden exhibit, transforming the art of origami into 20 colossal metal sculptures. Once you’ve walked through the exhibit, explore the garden grounds where you’ll come across native Florida plant species, a tropical fruit collection, a palm garden, and more.

6. Visit the Theme Parks

Visiting Orlando’s world-famous theme parks over Labor Day weekend is the perfect way to wrap up summer with a dose of magic and excitement. From the thrilling rides at Universal Orlando Resort to the enchanting experiences at Walt Disney World, it’s a great way to end the summer with a bang. Labor Day Weekend is also the start of EPCOT International Food & Wine Festival – one of Orlando’s beloved theme park events! During the festival, you’ll get the chance to experience dishes from countries all over the world. Indulge in seafood paella from Spain or try the festival-exclusive Huckleberry Funnel Cake. Your taste buds will thank you for the one-of-a-kind experience. 

Best Places to Stay in Orlando for Families

Looking for the best place to stay in Orlando this Labor Day weekend? If you’re planning a visit to Orlando over Labor Day weekend, our vacation rentals offer the ideal home base for your adventures. From Disney-themed accommodations to homes with private pools, there’s a rental to match every travel style. Enjoy the comforts of home in our vacation rental offerings with full kitchens, relaxing outdoor spaces, and easy access to all the Orlando Labor Day festivities.

 

 

A family enjoying the kitchen and dining room in their Vacation Rental home

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