Scariest places to go for Halloween

Estimated reading time: 2 minutes

Finding your fright this Halloween

Ghouls and ghosts around every corner, here are the best places to find your fright this holiday season.

Sleepy Hollow, New York

Yes, you read that right. You can actually visit Sleepy Hollow, the infamous grounds of author Washington Irving’s Headless Horseman. While there are no guarantees that you’ll spot the headless legend, Sleepy Hollow has been known to throw one epic Halloween party that will have your head spinning. Scare yourself silly with haunted hayrides, lantern-led cemetery tours, and dramatic reenactments of Irving’s dark tale.


For 14 nights only, Philipsburg Manor transforms into a twisted house of horrors crawling with the undead. Walk along a foreboding trail to the remains of Ichabod Crane’s schoolhouse. Prepare for ghoulish and twisting encounters with creatures that lurk in the shadows all while awaiting your inevitable meeting with the Headless Horseman himself. This exclusive event is not for children (nor the faint of heart)!

To enjoy something a little lighter, check out The Great Jack O’Lantern Blaze that features more than 7,000 individually carved and lit pumpkins. These are not your regular run-of-the-mill gourds. These jack–o’–lantern are transformed into giant works of art. Stroll alongside dinosaurs and dragons crafted from intricately carved pumpkins. This event is fun for the whole family. 

Viewfinder Tip: When booking ghost tours online, make sure you check the recommended age. Not every tour is going to be OK for small children, but some have other options for the kiddos.

Salem, Massachusetts

Salem is most known for its chilling past. For a city that was once vehemently against witchcraft of any kind, the Halloween season brings with it elaborate celebrations of what was once referred to as “the devil’s magic.” This month-long event, dubbed “Festival of the Dead,” features elaborate paranormal-themed activities like a psychic Fair, witchcraft expo, Salem Witches’ Halloween Ball, and graveyard conjures.

The Salem Witch Museum is an excellent place to acquaint yourself with the dark history of this charming town and to get into the Halloween spirit. If you’re in the mood to keep it a little lighter though, you can always go explore the historically rich waterfront. Better yet, book a witch tour and learn about the House of the Seven Gables—this mansion was the inspiration for Nathaniel Hawthorne’s creepy novel of the same name.

If you’re looking for authentic Halloween activities, then this town has you covered. From the Witch Dungeon Museum, a live reenactment of a 1692 Witch Trial, to the Gallows Hill Theatre and Museum there is something for everyone. Fires are burned on the city’s hilltops to mark this gathering of witches and ghouls.

Portland, Oregon

It is an undeniable fact that Portland is a weird place. That is what makes it so wonderful. Their commitment to the unusual is exactly what makes this city so incredible when Halloween rolls around. The Doll Asylum is a great example. Each year, the Scullie family spend weeks decorating their home with all manner of macabre dolls in gruesome scenes and then allow people to wander around looking at them for free. Maybe you want more? Portland also hosts a wide selection of haunted tours and costume competitions along with the Clark County Scare Grounds. Haunted houses and terrifying costumes stud the local fair grounds and offer a lot of options for getting scared.


This dark and rainy setting is also the perfect place to explore the Shanghai Tunnels. These secret tunnels were once used to shuttle drunk sailors onto ships where they would be kept as working prisoners for years at a time. Today, the derelict dungeons are open for tours.

Portland is also currently a hot spot for people dressed as terrifying clowns to wander around and set you on edge. For a truly terrifying Halloween, it would be hard to beat that.

Where’s the spookiest place you’ve spent Halloween?

Expedia compensates authors for their writings appearing on this site, such compensation may include travel and other costs.

Captain And Clark

Chris Staudinger and Tawny Clark (also known as "Captain and Clark") have spent the majority of their relationship exploring this great big world. After meeting on Kilimanjaro, courting in South Korea, getting engaged at the Taj Mahal, and sealing the deal in the Cascade Mountains, the two decided it was time to add another explorer to the mix. Traveling the world with kiddo-in-tow might alter the way they navigate the globe, but they welcome the challenge with open suitcases.

Chris and Tawny have had articles and videos published on USA TODAY TRAVEL, BBC Travel, Matador Network, as well as appeared as guest stars on TLC Asia's Fun Taiwan television series. When not on the road, you can find Chris and Tawny nestled in their home in Tacoma, Washington fueling up on coffee and cat cuddles while planning their future adventures. You can follow their travels on their blog, Instagram, and YouTube

Latest posts by Captain And Clark (see all)


Leave a Reply

Your email address will not be published. Required fields are marked *