If you’re planning a getaway to Hilton Head this October, you’ll find plenty of spooky, silly, and family-friendly events right here on the island. Grab your spooky get-up! Here are the top five Halloween events taking the island by storm in 2025.

Halloween on the Harbour

Head over to Harbour Town in Sea Pines on Sunday, October 26th, for one of Hilton Head’s most beloved traditions. Picture kids parading through the square in creative costumes, carnival games lining the walkways, and a pumpkin patch perfect for photos.

The highlight of this event is a costume contest that doubles as a runway show, where little ones strut their spooky or silly looks while parents cheer them on. It’s wholesome, lively, and the perfect community kick-off to Halloween week.

Halloween Wagon Ride

Are you up for something a little different? There’s fun on wheels to be had in Sea Pines when you hop aboard the Halloween Wagon Ride.

Taking place at Sea Pines Forest Preserve on Saturday, October 25th, the Halloween Wagon Ride is an immersive experience, featuring guides who’ll keep everyone laughing with Halloween trivia and games.

It’s part nature tour, part party on wheels. At just $16 for adults and $13 for kids, it’s an affordable way to add a memorable twist to your island stay.

Pumpkin Patch at Shelter Cove

Nothing says fall like pumpkins, and Hilton Head’s Pumpkin Patch at Shelter Cove Community Park is the place to find them.

On Friday, October 17th, the park transforms into a family festival complete with hayrides, crafts, bouncy houses, and of course rows of pumpkins waiting to be picked. If you’ve got little ones, this is the kind of afternoon outing they’ll talk about long after the trip ends. It’s a true community celebration that feels cozy and small-town — even with the Atlantic just down the road.

Trick or Trot 5K and Fun Run

Are you looking to balance candy with cardio? The Trick or Trot 5K and Fun Run hits the island on Saturday, October 25th.

Runners and walkers alike dress up in costumes for a spirited race through Hilton Head’s scenic paths. Whether you’re chasing a personal best or just out for the laughs (yes, tutus and capes are encouraged), it’s a festive way to start Halloween weekend.

Meowloween Halloween Bash

Animal lovers, this one’s for you.

The Meowloween Bash at Cool Cats Lounge combines a costume party with a good cause. Guests enjoy live music, themed cocktails, and a costume contest — while proceeds go toward local cat rescue efforts.

It’s quirky, it’s fun, and it proves Halloween on Hilton Head is for more than just kids.

Hilton Head Halloween Happenings Await!

From wagon rides through the woods to festive runs in costume, Hilton Head makes Halloween a season to remember — but all this Halloween fun can get you more tired than a zombie running the Trick or Trot 5K.

If you need a place to rest after a full day of island fun, look no further than Beachside Hilton Head.

Book your stay at a Beachside Hilton Head vacation rental today and be right where all the fun happens.