Twisty turns, dark shadows, and spooky apparitions. When it’s Halloween, it’s time for fun, with a little bit of freaky thrown in. Check out these road trips from major cities that will give you goosebumps.
1. NYC (Sleepy Hollow, NY): Horseman's Hollow
The town of Sleepy Hollow, just a couple of hours from New York City, is the setting of the spooky short story, “The Legend of Sleepy Hollow.”
Just about 30 miles from Manhattan lies a small town where an old ghost story about a headless horseman still spooks visitors today. For a Halloween scare, visit Horsemen’s Hollow: a spooky haunted house experience set on the grounds of the imposing Philpsburg Manor. Explore the grounds surrounding an old farm and mill that have been restored to feel just like the 1750s.
When the sun sets, take a lantern tour of Sleepy Hollow Cemetery, where the real author of the “Legend of Sleepy Hollow” (Washington Irving) is buried, along with famous rich guys Andrew Carnegie and William Rockefeller. At the Old Dutch Church, you can hear a live reading of the tale that made this sleepy town stay awake many a night.
2. Boston (Salem, MA): Salem Witch Museum
Less than an hour north of Boston lies Salem, known for its 1692 witch trials. Image courtesy of Getaway Mavens.
Salem, Massachusetts is synonymous with the occult, thanks to the tragically misguided Salem Witch trials of 1692 (told in horrifying detail by Arthur Miller’s 1953 novel, “The Crucible”). Since then, Salem has been a draw for real members of the Pagan and witch communities to gather, worship, and shop for crystal necklaces.
At Halloween, Salem pulls out all the stops and the whole town celebrates with everything from family-friendly costume parades and magic shows, to haunted harbor cruises, costume balls, and séances and psychic readings. Be sure to assign a designated driver, because Salem also loves its spirits of a different kind. Bars are packed with revelers through most of October. (“Let’s party, witches!”)
3. Philadelphia (The Pine Barrens, NJ): The Jersey Devil
A long-running ghost story has been scaring the devil out of Jersey campers for decades. Alleged sightings of the “Jersey Devil” have been reported since 1735, when a woman pregnant for the thirteenth time cursed her child to be a devil. It worked. The boy was born with wings, hooves, and a forked tail, and flew out the chimney and into the woods.
Is it true? Well, they named the NJ hockey team after him, so… Come hear the tale and try for a sighting. For 10 bucks, you can take a guided night hike and hear campfire stories accompanied by banjo and fiddle. Cider, hot chocolate, and donuts from the General Store should help settle your heebie jeebies.
4. Denver (Estes Park, CO): The Stanley Hotel
Does the Stanley Hotel look familiar? This haunted hotel is widely known as the inspiration for Steven King’s novel, The Shining. Image courtesy of the Stanley Hotel.
As far as scary movies go, “The Shining” is at the top of the list. Those little girls, the bloody elevator, the pages and pages of “All work and no play make Jack a dull boy.” Yikes. Now imagine visiting the inspiration for the fictional Overlook Hotel, where Jack Nicholson and Shelley Duvall become winter caretakers.“Solitude and isolation can, of itself become a problem.”
The Stanley hotel in Estes Park, Colorado is a turn-of-the-century resort nestled deep in the Rocky Mountains. In addition to fans of Stephen King’s novel and Stanley Kubrick’s film, spook-seekers will enjoy the Stanley for its own reputation for being haunted. The hotel offers Night Spirit Tours focused on the building’s rumored hauntings, and around Halloween puts on themed events like The Shining Ball (all costumes are “Shining”-related), a seriously lavish Halloween Masquerade party (already sold out, but you can start planning for next year), plus extravagant Murder Mystery dinners. I see dead people… Wait, wrong movie.
5. Seattle (Snohomish, WA): The Oxford Saloon
The spirit of the Wild West is alive (er, actually dead and haunting) at the Oxford Saloon. Known as Blackman’s Dry Goods store when it opened in 1900, it eventually became a saloon and a bordello. There have been numerous ghost sightings here, including the spirit of a sheriff killed during a bar fight, and a local businesswoman named Kathleen who has also shown her ghostly visage around the place.
The Washington State Ghost Society has investigated several times and gotten strong EVPs (Electronic Voice Phenomena). So, keep your eyes and ears open for spirits of all kinds when you mosey up to the bar.
6. The Bay Area (San Jose, CA): Winchester Mystery House
The Winchester Mystery House was custom-built for unusual inhabitants: ghosts. Image courtesy of Winchester Mystery House.
About an hour south of San Francisco in San Jose, you’ll find the Winchester Mystery House. The “mystery” involves a seriously long renovation project. Owned by rifle heiress Sarah Winchester, the house was under construction non-stop for 38 years. Upon her death in 1922, many of the rooms were left unfinished, leaving exposed studs and missing floorboards.
But the most perplexing part of the Mystery House is its bizarre design choices. There are staircases that lead to nowhere, doors that open to solid walls, a window built into the floor, and closets with a mere inch of storage space (not unlike some apartments in the Bay Area).
Legend has it that Sarah was convinced by a medium that her family was being haunted by the spirits of those killed by Winchester rifles. After the deaths of her daughter and husband, Mrs. Winchester feared she was next. Her medium told her to build a house for the spirits, and as long as construction never stopped, she would never die. But die she did, leaving a renovation story that beats the heck out of anything on HGTV.
7. Los Angeles (Long Beach, CA): Dark Harbor Tour
According to the website, the Dark Harbor Tour will “scare the ship out of you!” This haunted house comes with an immediate twist—it’s a boat.
Climb aboard the Queen Mary in Long Beach Harbor, and take part in seven terrifying mazes through the tight quarters of a luxury ocean liner. You can alight for dinner and drinks, or even stay the night, if you dare.
Watch out for roving monsters and chainsaw murderers when you grab a drink at the Meat Locker Bar, an icy bar built into a (fictional) chef’s meat locker. For more sophisticated spooking, eating, and drinking, visit the R.I.P. lounge, where the ghosts assumedly wear tuxes and ball gowns.