7 Spooky Halloween Road Trips to Creep You Out

halloween road trips
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Forget pumpkin spice – bring on scary movie season! As the weather starts to cool and leaves begin to turn, a certain portion of the population embraces the shift to the spookiest time of year. Ghost stories and creepy urban legends aren’t for everyone, but for the people attracted to the scarier parts of our culture, fall feels like a time meant just for us.

If you’re interested in the spooky and trying to figure out how best to celebrate it this fall, there are a number of great spots across the U.S. that have associations with dark or supernatural stories. We collected a few of the scariest or most infamous destinations for Halloween road trips. Now all we can say is proceed with caution…!  

1. Salem, Massachusetts

If you grew up in the U.S. (and maybe even if you didn’t) then you probably studied the Salem witch trials in school. The famous accusations of witchcraft and the panic they caused have made the city into a popular destination for tourists. And the city is happy to play up the darker aspects of its history with Halloween celebrations, a witch museum, and plenty of shops and events devoted to the spookier side of Salem.  

2. The Stanley Hotel

If you’re a Stephen King buff, then you’ve likely heard about the Stanley Hotel, the inspiration for the Overlook Hotel in The Shining. The hotel isn’t on our list merely as a destination for fans of the novel and film; it also has a reputation for being haunted. Located in Estes Park, Colorado, the hotel offers Night Spirit Tours focused on the building’s rumored hauntings, and around Halloween they put on themed events like Murder Mystery dinners and a masquerade party.

halloween road trips
The Stanley Hotel, inspiration for “The Shining” (Photo: Donna Greene)

3. The Myrtles Plantation

Rumored to be one of the most haunted houses in the United States, the Myrtles Plantation is a beautiful estate with a sordid history and plenty of stories about deceased guests paying visits to the living tourists that check in.  If you stay on a weekend, you can do the Evening Tour which focuses on the “mystery and intrigue” of the plantation.

4. Fort East Martello Museum

Ghosts are one thing, but creepy dolls are in a category all their own. The Fort East Martello Museum is part of the Key West Art and Historical Society, which sounds innocent enough, but it’s home to what’s been called the “world’s most haunted doll” (admittedly not the easiest claim to prove or measure). Robert the Doll has been accused of moving around on his own, giggling, changing his facial expression in response to conversations happening around him, and causing electronics to malfunction. If you can make it to Key West, Florida, you can visit him yourself for just $10.

5. Winchester Mystery House

Sarah Winchester inherited a fortune from the family business: guns. She feared the angry spirits of people who had been killed by her family’s handiwork and spent years turning an eight-room home into a massive mansion in the hopes of either hiding from or, in some strange way, appeasing the spirits she believed were out to get her. The home she left behind is a strange labyrinth full of symbols, stairs that go nowhere, and 160 rooms – some of them hidden. Visitors to the San Jose, CA home can tour a large portion of the rooms and see many of the bizarre attributes the mansion is known for. On some days in the fall, you can opt for the tour by candlelight.  

halloween road trip destinations
The 160-room Winchester Mystery House features hidden passageways, strange twisting hallways that lead to dead ends, false doors and even a séance room (Photo: Getty)

6. Shanghai Tunnels

The Shanghai Tunnels in Portland, Oregon have a seedy reputation going back to the city’s early history. While exploring badly lit underground tunnels is spooky under any circumstances, the Shanghai Tunnels get their name from an association with legends of men and women being “shanghaied” or drugged, dragged to sea, and sold into slavery. While historical evidence backing up these stories is scant, the legend remains and some locals claim the tunnels are haunted.

7. Bachelor’s Grove Cemetery

No list of spooky destinations is complete without a cemetery. Bachelor’s Grove Cemetery in Chicago, Illinois is a small, abandoned graveyard known for ghostly apparitions that range from your typical ghosts of people, to a strange sighting of a house where it doesn’t belong and colored lights where it doesn’t make sense for any to be.

Honorary Mention:

Warren Occult Museum. While currently closed, we feel the Warren Occult Museum still bears mentioning for future spooky road trips you may plan. It’s home to the famous Annabelle doll (yep, the one from the movies) and a number of other paranormal items collected by the famous parapsychologists in their years researching high-profile hauntings and demonic possessions. The Monroe, Connecticut museum is a go-to destination for anyone interested in the recent history of hauntings in the U.S.

The world is full of sites associated with the strange and supernatural. If you’re ready to hit the road to visit some of them (or if you want to see beautiful fall foliage by car), make sure you prepare properly to stay safe. You can’t do much to protect yourself from creepy dolls and ghosts (if you’d even want to) but you can take steps to minimize the risk of flat tires and car breakdowns. Do a little due diligence, then get out there and celebrate fall.