As Halloween approaches, the area around Regal Oaks Resort transforms into a hub of spooky, thrilling, and family-friendly events. Whether you’re in the mood for chilling haunted trails, a creative pumpkin painting session, or a full-blown Halloween celebration, there’s something for all ages. Here’s a rundown of the top spooky events near Regal Oaks Resort that you won’t want to miss this season.
Movies at the Garden Theater

Photo courtesy of Garden Theater
Location: Garden Theatre, Winter Garden
Dates: select days through October
If you’re a lover of horror, head over to the Garden Theatre in Winter Garden for their Halloween movie screenings. The venue, known for its rich history and charming ambiance, will host a series of classic and contemporary horror films, such as Carrie and The Blair Witch Project. Bring your friends, grab some popcorn, and enjoy a night of cinematic scares. Check their calendar for specific movie listings and times.
Pumpkin Painting Party at Cocktails & Screams

Photo courtesy of Cocktails & Screams
Location: Cocktails & Screams, Orlando
Date: October 20, 2024
If you’re looking for a creative and festive way to celebrate Halloween, the Pumpkin Painting Party at Cocktails & Screams is the perfect event. This 21+ event invites you to pick out a pumpkin, grab some paint, and let your artistic side shine. While you paint, enjoy a Halloween movie playing in the background, sip on themed cocktails, and savor spooky snacks. All painting supplies are provided, but you’re welcome to bring your own stencils or accessories to make your pumpkin truly unique. It’s a fun and laid-back way to get into the Halloween spirit. Be sure to reserve your spot here!
City of Winter Garden Halloween Experience

Photo courtesy of Winter Garden
Location: Downtown Winter Garden
Dates: October 18 – 31, 2024
Celebrate Halloween over two weeks in downtown Winter Garden with the City’s annual Halloween Experience. This family-friendly event features a hay maze, Halloween-themed photo stations, and an animated light show at City Hall. The entire downtown area is transformed with fall decorations and spooky displays, making it a perfect backdrop for a leisurely stroll or a fun photo session. Events vary per day, ranging from the Halloween Farmers Market to Lego Nights. Check out the full line up of events on their website!
A Petrified Forest

Photo courtesy of A Petrified Forest
Location: Altamonte Springs
Dates: select dates throughout October 2024
For those who crave the ultimate haunted experience, A Petrified Forest offers one of the scariest Halloween events in the country. Voted 4th Best Haunted House in the USA by USA Today’s 10 Best Reader’s Choice 2023, this event features three all-new haunted trails that will test your nerves and thrill your senses. Each trail is designed with elaborate sets, terrifying characters, and immersive effects that will leave you screaming for more. It’s an experience you won’t soon forget!
Haunting Nights & Happy Frights at Leu Gardens

Photo courtesy of Leeu Gardens
Location: Leu Gardens, Orlando
Dates: September 27 – October 31, 2024
Leu Gardens in Orlando hosts Haunting Nights and Happy Frights, an artful and spooky Halloween experience set in its lush forests. These two events feature a range of attractions. Happy Frights will be earlier in the evening with events designed for younger attendees and Haunting Nights will take place later in the evening. These spooky attractions will range from a hedge maze with a Minotaur to a carnival filled with crazy clowns. Guests can also enjoy hip-hop dancing aliens, a Dia de Muertos celebration, and encounters with a giant 12-foot spider. With fantastic food and drinks available, this event offers a unique blend of art, horror, and fun.
Halloween at Old Town

Photo courtesy of Orlando Attractions
Location: Old Town, Kissimmee
Date: October 31, 2024
For a classic Halloween experience, head to Old Town, right down the street from Regal Oaks Resort. On October 31st, the retro amusement park will host a free Halloween event featuring trick-or-treating, a costume contest, and entertainment throughout the night. It’s a great place to bring the kids for a safe and fun evening of Halloween festivities. The event captures the nostalgic charm of Old Town while offering plenty of spooky fun for the whole family.
Whether you’re looking for a thrilling haunted house, a creative night out, or a family-friendly Halloween celebration, the area near Regal Oaks Resort has an event for you. These spooky happenings will ensure your Halloween season is filled with fun, fright, and unforgettable memories.
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