Ava McDonnell
As summer comes to an unofficial end, Labor Day is a much-anticipated three-day weekend for many. It is filled with backyard barbecues, relaxing by the pool, and enjoying the last days of warm weather with family and friends. Labor Day celebrates American workers fighting for the rights we often take for granted today, like the eight-hour workday. So, if you’re looking for a fun-filled or relaxing day, we made a list of some events happening this Labor Day weekend.
Family Fun & More:
Promenade at Sunset Walk’s Labor Day Weekend Celebration (Kissimmee):
Date: Friday, August 29 – Monday, September 1
Location: Promenade at Sunset Walk, Kissimmee
Event Details: The Promenade at Sunset Walk is hosting a four-day Labor Day Weekend Celebration to mark the end of summer. Guests can enjoy a variety of entertainment, including live music, live DJing, and street performers, as well as a car show and an artisan market. The music acts include Luck of the Draw, Osaka Fall, and The Rundown performing on the Promenade Plaza Stage. Other live music can be found in the Euphoria Lounge, with performances by The Absent Trio, Folds & Williams, and Dennis Haklar. The event is a rain-or-shine affair and welcomes all ages. The event ticket is free with a reservation so make sure to secure your spot.
Tickets: Free Admission and Parking.
House of Blues Labor Day Bash:
Date: Sunday, August 31
Location: House of Blues, Orlando
Event Details: The House of Blues is featuring a lineup of popular dance and electronic DJs. Scheduled to start at 7:00 p.m., will focus on performances by DJs Icey, Magic Mike, Baby Anne, Kimball Collins, and Jimmy Joslin. It is a general admission, standing room only event, and guests are encouraged to arrive at least 20 minutes before the scheduled start time. This is also an all-ages event, with tickets available for purchase online.
Tickets: $48 per person.
Date: Friday, August 29 – Saturday, August 30.
Location: Food Trucks Heaven, Kissimmee
Event Details: From 6:30 PM – 11:30 PM, Food Trucks Heaven is hosting a “Labor Day Kickoff Weekend” event to celebrate the holiday. The family-friendly event will feature over 50 food trucks, an array of culinary options from Mexican to Asian to classic sweet treats and more. In addition, guests can enjoy a live DJ, indoor and outdoor seating, and a raffle for a $100 voucher on Saturday. Admission and parking is free, making it an accessible and fun outing for all ages.
Tickets: Free admission and parking.
Date: Friday, August 29 – Monday, September 1
Location: Raglan Road Irish Pub & Restaurant at Disney Springs, Lake Buena Vista
Event Details: Spend your Labor Day weekend immersed in a celebration of all things Irish hosted at Raglan Road Pub in Disney Springs. This festival features non-stop live music from top bands hailing from Ireland, playing everything from traditional tunes to folk and blues. Bands include Strings and Things, Bridin Brennan, Byrne Brothers, Plain Sailin, Men of Aran, and Northern Crossing. Beyond music, you can enjoy performances by Irish dancers and savor authentic Irish cuisine and drinks.
Tickets: Free entrance.
Courtyard Labor Day BBQ and Pool Party:
Date: Monday, September 1
Location: Courtyard by Marriott Titusville Kennedy Space Center, Titusville
Event Details: The Courtyard Titusville Kennedy Space Center is hosting a pool party for the upcoming Labor Day weekend. The event will feature poolside BBQ with a choice of cheeseburger or hot dog meal, a kid-friendly splash zone, and live music from the “Just BE Duo” from 1:00 PM to 4:00 PM. The hotel’s pool bar will also be open for drinks and guests are encouraged to bring their own pool towels in the event that hotel supplies run out. Purchase tickets here which include one meal voucher.
Tickets: $30 for ages 13+, $15 for ages 3-12, free admission for ages 2 and under.
Get Active with a Race:
For those who want to start their holiday weekend with a dose of adrenaline, several races are taking place near you. Check out each race to sign up before spots fill.
Ritz-Carlton Grande Labor Day Weekend 5K:
Date: Sunday, August 31.
Location: The Ritz-Carlton Grande Lakes, Orlando.
Event Details: This family-friendly walk or fun run takes place on the back nine of the Grande Lakes Resort 18-hole golf course. Participants can enjoy post-race refreshments like champagne and mimosas, assortments of snacks, and a Theragun massage done by Grande Lakes therapists. They also offer a yoga class for after the race. The race starts at 6:30 AM and is open to all resort guests as well as the general public of any age.
Tickets: $75.00 for adults , $50 for ages 12 and under.
Date: Sunday, August 31.
Location: Harbor Park, Lake Baldwin, Orlando.
Event Details: A tribute to American workers, this race features a scenic and shaded course around Lake Baldwin. All participants will receive a race shirt, finisher medal, and swag bag. Awards will be handed out for the top three finishers in the following categories: Overall Male and Female, Ages 10 and under, 11-15, 16-19, 20-29, 30-39, 40-49, 50-59, 60-69-70-79, 80+. Special pricing is available for military, veterans, first responders, and kids.
Tickets: $40 for adults , $20 for ages 0 – 17.
Date: Saturday, August 30 – Monday, September 1
Location: Cady Way Park, Winter Park.
Event Details: This unique three-day running event invites runners of all skill levels to participate in a 50K, marathon, half marathon, 10K, or 5K. The scenic races take you through areas of Cady Way Park, offering a fun and relaxing running experience. This race is self-described as “casual” and “low-key,” so perfect for beginners of all ages. Participants do not receive gifts or prizes but offer a great time for all. When signing up, pay attention to the various start times per race.
Tickets: 50K $75 – $205, $65 – $175 marathon, $55 – $145 half marathon, $40 – $10510K, $30 – $75 5K.
Whether you’re dancing to live music, enjoying family-friendly fun, or hitting the pavement for a refreshing 5K, Orlando’s Labor Day Weekend is packed with options to create lasting memories. It’s the perfect opportunity to squeeze out every last drop of summer before the fall season officially arrives. We hope you have a fun Labor Day!
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