It is hard to believe, but Labor Day Weekend is here and fall fun has arrived! The much-anticipated season of Magical Dining is now here, too. Let's take a look at the best events and things to do this week.
Updated multiple times each week by Nancy DeVault, Dani Meyering, and Kelly Lamano Diaz
Attention Parents: Head to Orlando-Parenting.com for things to do with kids in Orlando.
Featured Events
Giving an extra shoutout to the following events, which help us to bring this guide to you for FREE!
High Point Climbing and Fitness Grand Opening
Thursday, August 28, from 6-9 p.m.
1978 Stanhome Way, Orlando, FL 32804
The Packing District
Celebrate the grand opening of High Point Climbing and Fitness: Orlando in The Packing District on Thursday, August 28th from 6–9 PM! Enjoy an evening of live music, local food vendors, climbing demos, giveaways, and more. Perfect for adventurous date nights, this state-of-the-art facility offers rope climbing, bouldering, yoga, and fitness in a vibrant, wellness-focused community. Whether you're a first-timer or seasoned climber, come experience Orlando’s newest destination for fun and connection. Free and open to the public!
Jerry’s Girls
August 7 – 31st, showtimes at 2pm or 7:30pm
Orlando Shakes, 812 E. Rollins St. Orlando FL 32803
The Winter Park Playhouse Proudly presents Jerry's Girls – a dynamic Broadway musical revue that celebrates the music of the incomparable composer Jerry Herman! This show highlights music from such immortal musicals like Hello Dolly!, Mame, La Cage Aux Folles and more. Tickets from $20.
Fireside Tastings
Select Saturday Evenings
Sear + Sea Woodfire Grill, JW Marriott Orlando Bonnet Creek
14900 Chelonia Parkway, Orlando, FL
Experience an all-new, exclusive seven-course Fireside Tasting at Sear + Sea Woodfire Grill. An intimate, chef-guided journey hosted directly in front of the woodfire grill, this immersive dining experience begins before the restaurant opens, offering a rare behind-the-scenes look at this Michelin-recommended culinary craft. Each course is meticulously prepared using premium seasonal ingredients, highlighting the richness and refinement of open-flame cooking and expertly paired with wines selected to complement and elevate the flavors of the evening. Select Saturday evenings, $250 per person, book on OpenTable.
River Country Water Park – NOW OPEN!
Westgate River Ranch Resort
3200 River Ranch Blvd, River Ranch, FL 33867
Get ready for splash-filled adventures at River Country Water Park! Splash through thrilling water slides or take a refreshing dip in the pool. Whether you're soaking up the sun or relaxing poolside, there's no better place in Lake Wales for a full day of fun. Plus, book early at RiverCountry.com and score free water park tickets, making your stay even more unforgettable.
Read More on Westgate River Ranch's Day Passes HERE.
This Week Events in Orlando, Things to Do August 25-August 31, 2025
Halloween at Disney Springs is happening now! This includes one of the best Halloween Bars in Orlando!
Jerry’s Girls
Through August 31st, showtimes at 2pm or 7:30pm
Orlando Shakes, 812 E. Rollins St. Orlando, FL 32803
The Winter Park Playhouse Proudly presents Jerry's Girls – a dynamic Broadway musical revue that celebrates the music of the incomparable composer Jerry Herman! This show highlights music from such immortal musicals like Hello Dolly!, Mame, La Cage Aux Folles and more. Tickets from $20.
Magical Dining
Through September 30, 2025
160 restaurants
Here's your chance to dine at some of the best restaurants in Orlando. During Magical Dining you can enjoy a three course meal for just $40, and in some of Orlando's most luxurious locales, $60. A portion from the proceeds of this event benefits multiple charities.
Preserving Your History Series: Making a Time Capsule
Wednesday, August 27, 2025, 1-4pm
Orlando History Center
65 E. Central Blvd., Orlando, FL
This event, priced at $20, helps attendees create time capsules to preserve heirlooms, including photographs, jewelry, fabric and more. Bring items that can fit within a 12”x10”x5” box.
Boards & Books: A '90s Game Night
Wednesday, August 27, 2025, 7-9pm
Azalea Lodge at Mead Botanical Garden
1300 S Denning Dr, Winter Park, FL 32789
Get ready for a night of board games, bookish vibes and 90s nostalgia! Hosted by The New Romantics bookstore and The Haven Games, mix and mingle with fellow readers while trying out new games, enjoying throwback '90s tunes, and snacking on themed treats provided by Events by Dubsdread. Whether you're new to board games or a seasoned player looking for community, this cozy, playful event is for you!
Tickets $20
WaWa Summer Fun Days at Bok Tower Gardens
August 28 & August 29, 2025
Bok Tower Gardens
1151 Tower Blvd., Lake Wales, FL
This is the last Thursday and Friday of the Summer Fun Days, offering free admission.
This complimentary offer is limited to four visitors per registration (hello double date opportunity).
Metamorphosis: An Arts and Music Project
Friday, August 29-Sunday, August 31, 2025
Orlando Amphitheater at Central Florida Fairgrounds
4603 W. Colonial Drive, Orlando
This three-day event is described as an immersive environment intended to inspire attendees to explore their artistic potential and connect with others through the universal languages of art and music.
Adult Recess Back to School
Saturday, August 30, 2025, 5-8pm
Deviant Wolfe Brewing
121 W 1st St, Sanford, Florida 32771
School is back – but this time, it's for the grown-ups. What's on the syllabus? Test your brain on 90s & 2000s pop culture, school subjects and more! Enjoy a spread of childhood favorites with an adult upgrade. Sip on nostalgia with the Teacher's Pet – Cinnamon Apple Whiskey Seltzer cocktail. Plus, donate a school supply item and add your deets to the list for a chance to win prizes.
The Changing Face of Orlando: A Sesquicentennial Celebration
Through Sunday, August 31, 2025
Terrace Gallery at City of Orlando
400 S. Orange Ave., Orlando
Throughout 2025, the City of Orlando is celebrating its 150th anniversary with numerous events. This is your last chance to partake in a visual journey through time, pairing 12 historic photographs of Orlando with modern-day recreations that spotlight the city's evolution over the last 150 years.
Labor Day Weekend at Boxi
Thursday, August 28 – Monday, September 1
Boxi Park – Lake Nona
Head to Boxi Park for a long weekend of live music, DJs, food & drink specials, and family fun on Sunday.
FREE
FIND MORE: Labor Day Weekend Events
EPCOT International Food and Wine Festival
August 28 to November 22, 2025
EPCOT
Eat and drink your way through the park’s largest culinary fest on Labor Day!
Theme park admission required; food and beverage additional cost
Annual Labor Day 5K
Sunday, August 31, 8am
Harbor Park
4990 New Broad St, Orlando, FL 32814
The Southern Timing Foundation, Inc hosts the 5th Annual Labor Day. This race will be RFID chip timed and all participants will receive a performance race shirt, finisher medal, snacks and other drinks, and a swag bag filled with donated items from sponsors. This race will start and finish at the beautiful Harbor Park at Lake Baldwin. This scenic course will take you out and back around the lake, there is plenty of shade all around the course.
$35
Next Week: Things to Do September 1-7, 2025
Luminary Market and KaleidoScope 360° Movie Night
Wednesday, September 03, 2025, 5:30-9pm
Luminary Green Park, Creative Village
437 North Terry Avenue, Orlando, FL 32801
This monthly market (hosted the first Wednesday of each month) showcases 20+ vendors, focused on celebrating and supporting the growing Creative Village community. In addition to the shopping experience, KaleidoScope 360° (produced by Global Peace 360°) will show at 7pm.
LNPC’s FREE Community Yoga Class
Thursday, September 4, 2025, 12-1pm
Wave Hotel –Sculpture Garden
6775 Chopra Terrace, Orlando, FL 32827
During these dog days of summer, find your downward dog at a free session offered by Lake Nona Performance Club. FYI, if you miss this week, know that this opportunity is offered every Thursday.
Hokus Pokus Live
Thursday, September 4, 2025, 8pm
The Plaza Live
425 N. Bumby Ave., Orlando, FL
Ready for spooky season? This production stars legendary drag superstars (Ru Paul’s Drag Race) Ginger Minj, Jujubee and Sapphira Cristal. The show is geared for those 18+, with hauntingly hilarious comedy, impressive vocals and a touch of magic.
House Of Bey: A Beyoncé Birthday Celebration
Thursday, September 4, 2025, 9pm
The Beacham
46 N. Orange Ave., Orlando, FL
Grab your girls (or your love) to dance the night away to Queen Bey. Expect the DJ to celebrate her discography, from Lemonade and Renaissance to Dangerously In Love and I Am…Sasha Fierce.
Gateway Winter Park’s Pickleball Open Courts & Lessons
Friday, September 5, 2025, 9am-1pm
Gateway, 701 Formosa Avenue, Winter Park, FL
Need to stick to a date night budget? No big dill! On Fridays, Gateway offers indoor pickleball sessions for just $5 per person. Paddles and balls provided. Better yet, first-timers get their first session at no cost.
Leu Gardens Movie Night
Friday, September 5, 2025, 6-9pm
1920 N. Forest Ave., Orlando, FL 32803
Dinner and a movie on date night? Yes please… but with dinner being an al fresco picnic in the lush grounds of Leu Gardens. Gates open at 6pm, with an outdoor screening of Indiana Jones and the Last Crusade set to follow. Cost: $10 adult, $8/child.
House and Coffee
Saturday, September 06, 2025, 8am-2pm
Qreate Coffee
1212 Woodward Street, Unit 1, Orlando, FL
House & Coffee at Qreate is a high-energy community event where music meets caffeine. It brings together DJs and a full morning of house beats, specialty drinks and creative vibes. Think open-air patio morning party celebrating all things coffee and connection. Remember, coffee makes couples happy… because caffeine has been shown to trigger the production of dopamine in the brain and, thus, trigger (warm and yummy) cheeriness.
Baldwin Park Porch Sale
Saturday, September 6, 2025, 8am-noon
1913 Meeting Place, Orlando, FL
The Fall Porch Sale returns to Baldwin Park. Shoppers can find treasures from hundreds of participating vendors, as well as purchase fresh coffee from Lobos Coffee Roasters.
Digital Painting for Adults
Saturday, September 6, 2025, 10am-1pm
The Maitland Art Center-Studio 10
231 W. Packwood Ave., Maitland, FL 32751
If you and your love just love digital painting, this workshop is the date night (well day date) for you. Hurry! It’s super limited for an intimate group setting to achieve personalized support using the free Sketchbook App. This workshop is priced at $140.
Winter Parktoberfest
Saturday, September 6, 2025, 4-10pm
Mead Botanical Garden
1300 S. Denning Drive Winter Park, FL
Hosted by The Winter Park Rotary Club, in partnership with Licorice Sticks Entertainment and Hollerbach’s Restaurant, this second annual event kicks off the fall season with a traditional flag ceremony and “Tapping of the Keg” led by Winter Park Mayor Sheila DeCiccio. Expect food, festive fun and fall vibes. Cost: $25 (kids free with paid adult).
Fall Back 90’s Block Party
Sunday, September 7, 2025, 1-6pm
David’s Cuts Barbershop, 2050 State Road 436, Suite 120, Winter Park, FL
This 90’s themed block party will feature food trucks, vendors and local businesses, free haircuts from local barbers and much more. Dig through your closet to find those 90s tee’s, big sunglasses and jean jackets.
Twerkchella: Art of Seduction
Sunday, September 7, 2025, 6pm
The Abbey
100 S. Eola Drive, Orlando, FL
Those looking for something pretty sexy to round-out their Sunday Funday may want to snag tickets to Twerkchella: The Art of Seduction. This stage production is for 21+ and a swanky attire affair.
Later in September
Amber Brooke Farms
5th Annual Fall Fest
Saturdays & Sundays, from Sept. 20 – Nov. 2
Celebrate fall at Amber Brooke Farms during the 5th Annual Fall Festival: “Harvest on the Hill.” From flower fields and live music to archery, gel blasters, yard games, and fall-themed fun, there’s something for every member of the family. Enjoy delicious food, hands-on activities, and beautiful photo spots throughout the farm. Located in Eustis, FL, tickets start at just $15.95 online. Make it a season to remember!
Monster Moku
DoubleTree SeaWorld Orlando
Thursday – Sunday, from Sept. 25-28, 2025
Get ready for this three-day, 21+ cocktail-driven, tiki-meets-horror spectacle like no other! Roam through eerie pathways, marvel at Polynesian fire dancers and the gleaming chrome of a vintage car show, rock to the bone-rattling live surf bands, and dive headfirst into a weekend bursting with monstrous fun, dark tropical thrills, and unforgettable surprises.
Tickets start at $95
Tonka’s Country Fall Festival
Saturday, September 27, 4pm – 10pm
Lake Mary Pub & Tiki Bar, 119 W Crystal Lake Ave, Lake Mary
Celebrate the arrival of fall with a community festival inspired by Tonka the horse, a beloved pub regular. Enjoy a hay ride through Downtown Lake Mary, carnival games, bull riding, a dunk tank, local vendors, food trucks, live music, and drink specials. Family-friendly fun — all ages welcome.
Weekly Ongoing Orlando Events
Wine Wednesdays at NORMAN’S Orlando
Wednesdays from 5:30-7:30 p.m.
7924 Via Dellagio Way, Orlando, FL 32819
Head to NORMAN’s on Wednesdays for summer specials featuring 30% off select bottles of wine, curated by their Sommelier! Plus, try their new “Flights & Bites” offering hand-picked Red, White, and Sparkling Wines paired to complement the Chef-curated Bites Menu. You can also book a 15-minute tasting session with our Sommelier to learn about wines, regions, and pairing suggestions (complimentary tastings included). Can’t go on a Wednesday? NORMAN’S offers daily Happy Hour from 5-7 p.m. with dinner available until 10 p.m.
AC Orlando Downtown Express Lunch
Lunch served Tuesday-Friday 11am-3pm
333 S. Garland Ave, Orlando, FL 32801
Introducing AC Hotel's new Express Lunch—crafted for those on the go but unwilling to compromise on flavor. For just $18, enjoy a chef-inspired entrée and a non-alcoholic beverage, all guaranteed to be served within 20 minutes of ordering. Perfect for a power lunch or a quick catch-up, it's speed without sacrifice. Available Tuesday-Friday—because great taste shouldn't have to wait.
Pottery Night
One Thursday Every Month, from 6:30-8 p.m.
8602 Universal Blvd, Orlando, FL 32819
Discover the magic of pottery in this 2-hour group session at the Castle Hotel! Guided by a skilled instructor, you’ll master the basics of throwing clay on the pottery wheel and create your very own unique piece. From shaping the clay to glazing for a polished finish, this experience offers hands-on fun from start to finish.
ICEBAR Orlando Epic Summer
May 15 – September 1, 2025
ICEBAR's summer lineup includes themed cocktails, a liquor-infused ice cream bar, weekend DJs, live ice carving shows, and the brand-new Tiki-themed ICEBAR Beach Club. Enjoy games, giveaways, and lively parties throughout the season.
Bonus: Show your Epic Universe ticket for free entry Sunday through Thursday and half-off entry on Fridays and Saturdays.
Related post: Things to Do at CityWalk
Makers Market at Forward/Slash Distillery
The Last Saturday of Every Month, from 2-6 p.m.
650 S Capen Ave, Winter Park, FL 32789
Support your local Orlando makers at Forward/Slash Distillery’s monthly Makers Market. Hosted by Orlando Local Maker’s, this event features the best of vendors who craft and make various items, goods, trinkets, and gifts. The market is on a break for summer and will return on September 27th. Food will be served by Bien Fuego BBQ for some light bites while you shop. Free to attend!
Happy Hour + Art @TheFalconBar
Mondays from 6:30-10pm
The Falcon Bar & Gallery
819 East Washington Street, Orlando, FL 32801
Local vibes. Awesome people. Enjoy Happy Hour adult libations while viewing local art at one of Orlando’s favorite local spots for creatives!
FREE Admission
Tasty Takeover in The Milk District
Tuesdays from 6:30-10pm
The Milk District – E. Robinson St
THE food truck block party in Orlando! Find it in The Milk District every Tuesday night behind the bars and shops of E. Robinson St.
FREE Admission
Game & Hobby Night at The Burrow
Every Tuesday, 5pm – 8pm
The Burrow Cafe & Play, Mills area
Bring along your favorite game, knitting project, book, or enjoy one of the games available at The Burrow. Come relax, be playful, and enjoy your favorite hobby or discover a new one. Free to attend and drink specials available.
Luminary Market
First Wednesday of every month, 5:30-9pm
Luminary Green Park in Creative Village
Explore 20-25 local vendors featuring unique, curated goods and support our growing community of residents, students, and workers. Stick around after shopping for KaleidoScope 360°, an outdoor movie series where you can enjoy family-friendly films under the stars! Showtime is at 7pm.
Late Night Thursdays
Thursdays, 5pm – 8pm
Leu Gardens
Bring a picnic & seating, sip some spirits, or take a stroll through the gardens and discover the amazing ORIGAMI IN THE GARDEN exhibit. Included with general admission. Rain or shine.
$15 per adult, $10 per child
Piano Bar Show at Jewel
Friday and Saturday Nights
Jewel Orlando
Dueling Piano players take the stage for a fun night of song requests and sing-alongs! Call (321) 444-5306 after 5pm to get your password for speakeasy entry.
FREE admission with password
Cirque du Soleil “Drawn to Life”
Wednesdays – Sundays
Performances of “Drawn to Life” take place on most nights at 5:30 pm and 8:00 pm. Go for the later show if you prefer to potentially have less kids in attendance. Additionally, it will give you more time to enjoy Disney Springs before the show.
Weekends at the Winery
Saturdays and Sundays, 10am – 5pm (Sat) & 11am – 5pm (Sun)
Lakeridge Winery
Head to this Central Florida winery's expansive vineyard green each weekend for delicious food, live entertainment, complimentary wine tastings/tours, and Lakeridge wines by the glass at the outdoor bar. Plus, delicious food at the Food Pavilion, as well as live music all weekend long.
FREE admission
Check out multiple Farmers' Markets around Orlando every weekend.
Saturday Exhibition Highlights Docent-Led Tour
Every Saturday, 1pm & 3pm
Rollins Museum of Art
Docent-led tours of highlighted works from the season’s exhibitions at the Rollins Museum of Art.
FREE
Dinks & Drinks
Every Saturday, 6:30-9:30pm
ClearOne Sports Centre
4141 N. John Young Parkway, Suite 3, Orlando
Open courts for casual drop-in play. Includes 1 free drink (Beer, High Noon, or Soda). Paddle rentals are available for $5. Tennis shoes required. Different music theme each week. No partner? No experience? No problem. This is the perfect night to bring a friend, meet new people, or just vibe with the community.
$20 per person
Read more: Places to Play Pickleball in Orlando
Tai Chi in the Garden
Every Saturday through 2025, 10:30am – 11:30am
Mead Botanical Garden, 1300 S. Denning Dr, Winter Park
A gentle exercise program that is composed of slow deliberate movements, meditation, and deep breathing to enhance health and well-being.
$15
October Preview
Clermont Harvest Festival
Clermont Main Street
Saturday, October 25, 2025 10am – 4pm
Fall fun is calling! Over 100 artisan vendors, a costume contest (for people and pets!), kids zone with fun activities, live music, and food trucks. Bring the whole family out for a festive day of fall vibes, fun, and community!
AC Sky Bar Adult Halloween Costume Party
Friday, October 31, from 5-11 p.m.
AC Sky Bar, 333 S Garland Ave, Orlando 32801
Head to AC Sky Bar for a creepy, 21+, fun-filled night featuring Halloween-inspired cocktails and bites. DJ Dracula will be spinning spooky sounds of the season. Expect dancing, party favors, and more; Appropriate attire required.
MORE: 31 Halloween Season Date Ideas
November Preview
16th Annual Walt Disney World Swan & Dolphin Food and Wine Classic
Friday-Saturday, November 14-15, from 5 p.m. – 9 p.m.
1200 Epcot Resorts Blvd., Lake Buena Vista, FL 32830
Get ready to sip, savor, and stroll under the stars at the Walt Disney World Swan and Dolphin Food & Wine Classic! Indulge in a world-class celebration of global flavors, fine wines, and craft beers—all just steps from EPCOT. With unlimited tastings, live entertainment, and breathtaking ambiance, it’s the ultimate evening escape for foodies and fun-seekers alike. Don’t miss your chance to experience this unforgettable culinary event. Tickets are limited—get yours now at FoodAndWineClassic.com!
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