Who remembers the joyous feeling of coming home from school to slip on your Halloween costume and run around the neighborhood gathering free candy? It was such a good time back then. For a few hours, you could choose to be anyone or anything you wanted. You got to (literally) walk around in someone else’s shoes, and it didn’t matter if the shoes were oversized clown shoes, unicorn hooves, or Hobbit feet.
If you’re having a hard time remembering that care-free feeling, then we’ll attempt to scare you instead. Our travel-loving ghouls rounded up vacation ideas for a holiday filled with spectacularly spooky events, hair-raising historical tours, and even some haunted hotels.
3 Spooky Towns to Visit This Halloween
Haunted houses, carnivals, and pumpkins are everywhere in October, but in these three cities, you’ll find something more. Whether you’re looking for something off the beaten path (and completely underground) or the city with the most witches, this list has something frighteningly fun for you.
1) Salem, Massachusetts
In the northeastern corner of the tiny state of Massachusetts, you’ll find Salem. It’s best known as the Puritan village full of witch-hunt hysteria, which ended with 19 men and women convicted and executed as witches during the last decade of the 17th century. The tragic details of the events are written in the annals of American history and, with help from the literary and film world, they continue to fill our heads with images of witches, magic, and the occult.
The modern-day descendants and current inhabitants of Salem embrace their history and throw a month-long party in October every year called Haunted Happenings. From the Salem Psychic Fair, Witches Market, and the Dumb Supper to the Haunted Biz Baz Street Fair and the Little Munsters Hotel Bash, anytime you visit in October your schedule can be as full of historical happenings as you have energy to attend.
If you get lucky, you might be able to book a room at the historic (and supposedly haunted) Hawthorne Hotel. It was named after famous author and native son Nathaniel Hawthorne and is said to be built on land where an apple orchard owned by Bridget Bishop, the first person executed in the witch trials, once stood. Guests at the hotel experience specters of former Salem residents and claim they smell apples even when none are on the menu.
Are you brave enough to plan a Salem vacation?
2) Sleepy Hollow, New York
The town of Sleepy Hollow, which once only existed in the fictional story written by famous author Washington Irving, officially became a town in 1996. The official name may be relatively new but the area north of Tarrytown, New York, has long been known as the geographical inspiration for the spooky tale. Even 200 years after publication, just the mention of the Headless Horseman can haunt your imagination.
When you plan your spine-chilling holiday to the Hudson Valley, you take a step backward in time. You can visit all the historical sites in Sleepy Hollow, from the Headless Horseman Bridge and the Sleepy Hollow Cemetery to the Rockefeller Estate and Washington Irving’s home, Sunnyside.
Craving more sinister stops? The historic Philipsburg Manor transforms into Horseman’s Hollow for 16 nights during the Halloween season and claims to take the tale to “the darkest extremes.” The haunted trail takes over the historic grounds and if you’re lucky (or unlucky?) you might catch a glimpse of the Headless Horseman himself.
For a more family-friendly Halloween experience, enjoy the Great Jack-O‘-Lantern Blaze, just a few miles away at Croton-on-Hudson. While there, you’ll wander through the immersive exhibit illuminated by more than 7,000 hand-carved jack-o’-lanterns. You’ll see a medieval castle, a flock of jack-o’-lantern owls, walk the Pumpkin Zee Bridge, and discover the Pumpkin Planetarium.
If you book a room at the Tarrytown House Estate & Conference Center, you’ll find more than just a comfy place to lay your head. This estate offers activities galore, including indoor and outdoor swimming pools, racquetball and tennis courts, volleyball, and bocce ball. After all those activities, you’ll be ravenously hungry, but they have you covered with a full breakfast buffet and a top-notch evening dining experience at Cellar 49—the Tavern at the Mansion.
3) Portland, Oregon
Sometimes referred to as one of the most haunted places in America, the tunnels beneath Portland, Oregon, are as old as the city itself. Originally built to allow bars and restaurants easy access to their supplies, the tunnels provided the ability to quickly move items from the waterfront to their establishments. Yet, it wasn’t long before the tunnels took on a more sinister role. Nefarious persons involved with the various businesses, bars, taverns, and brothels connected to the tunnels began installing trap doors. Unsuspecting customers could be dropped directly into the darkness of the tunnels.
Sometimes, the victims would then be sold into slavery, often on a ship bound for eastern Asia. Thus, the practice was dubbed being “Shanghaied.” Thousands of people were lost to the “Shanghai Tunnels” in the city known to many as “The Shanghai Capital of the World,” but luckily not everyone who dropped through the trap doors became a slave.
If you’re looking for a real-life paranormal experience, book a visit to the Shanghai Tunnels and you could meet some of the more famous spirits who are said to haunt the place. Beyond the crying, moaning, and wailing tourists report hearing in the tunnels, one spirit is said to linger nearby. “Nina” haunts the area near a pizza parlor connected to the underground passageways called “Old Town Pizza” and she has been known to tug on people’s clothing as they pass by her.
If you’re brave enough to stay in the historic district and risk the hauntings, and the chance of being dropped into the Shanghai Tunnels (kidding, this doesn’t happen anymore), try the Hoxton Portland Hotel. Not only are you blocks away from the tunnels and all the sites found in Portland’s Old Town Chinatown, but you’ll be wrapped in comfort and luxury. Three dining options are spaced throughout the hotel—in the basement, on the main floor, and the rooftop—so no matter where you are in the hotel, you’ll never be too far from something delicious.
3 Haunted Hotels You Can Actually Stay In
You can make it feel like Halloween any time when you book a room at one of these famously haunted hotels, all bookable through roomkey.com.
Stephen King’s 1974 stay in this famous hotel inspired his novel “The Shining,” which in turn inspired Stanley Kubrick’s horror film classic of the same name. Even though the hotel is more than 100 years old, its history isn’t actually packed with dreadful events. However, that didn’t stop the Stanley Hotel from gaining notoriety for paranormal activity by the 1970s, which is a reputation it holds to this day.
Guests regularly share stories of ghostly figures popping up in photographs snapped while staying at the haunted hotel. One such photo wasn’t discovered until the family returned from their trip and were looking through photos on a smartphone. The figure of a little girl (who hadn’t been on their tour) appeared to be descending a set of stairs. Ben Hansen, former FBI agent and TV show host, examined the photo and was unable to find any signs of trickery.
Making the Stanley Hotel part of your vacation may not result in any scary stories, but the history and excitement of a tour there is bound to be full of incredible stories.
You’ll find another famously haunted hotel in the Lone Star State named after the Civil War veteran Jesse Driskill, who built the Austin landmark in 1886. It’s been said, even after his passing, that Driskill regularly checks in on the luxurious Driskill Hotel, as he is one of the specters guests claim to encounter (along with his lingering cigar smoke scent).
Two more tales of tragedy explain the hauntings guests recall experiencing during their stay. The first story is reported to have happened shortly after the Driskill’s opening in 1887 when the young daughter of an important guest was chasing her ball and tumbled down the Grand Staircase to her death. The most frightening story is that of two brides separated by 20 years, who were both spending their honeymoon in Room 525 and for reasons lost to time, both committed suicide in the hotel room.
Whether or not you experience any of the ghostly happenings while staying at the Driskill Hotel, the grandness and luxury of the late 19th century surround you. The polished marble, grand columns, and Victorian-style paintings transport guests into the age of our ancestors.
Among the glitz and glamour of Hollywood, you’ll find the Hollywood Roosevelt Hotel, which opened in 1927 and boasts 12 stories, 63 suites, and 300 guest rooms. Its fame grew each time a new celebrity visited or made the luxurious space their home, but the paranormal notoriety blossomed as rumors grew about two of those celebrities continuing their residence within the hotel after their death.
Iconic beauty, model, and movie star Marilyn Monroe’s spirit is said to haunt suite 1200, where she lived for two years as her modeling career took off. Guests staying in her suite claim to remember seeing her image sharing space in the mirror. Academy Award-nominated actor Montgomery Clift is another celebrity whom guests claim they’ve encountered, both in and around his former room. People say this phantom gently bumps against guests who get near his room and they often hear him playing his trumpet.
If you can’t stay in one of the famous rooms, you still have a chance to encounter one of the ghostly apparitions that guests report having seen—a 5-year-old girl looking for her mother, an Academy Award nominee, or a ghost piano player.
While staying at the hotel, there are many options for enjoying food, drinks, and fun where celebrities have frequented since the 1920s. Stroll through the historic lobby, visit the Blossom Ballroom where the first Academy Award ceremony was held, try a burger at 25 Degrees, or take a plunge at the Tropicana Pool & Café.
Plan Your Terrifying Trip Today
This Halloween, plan a getaway that’s both frightening and fun. But don’t forget to book through roomkey.com so the frightening part isn’t finding your perfect hotel room. We don’t pressure you into booking a hotel before you’re ready, and we won’t hide behind the fine print like some other travel sites do. When you choose Roomkey, you’ll have a simple and honest hotel search experience. Normally, our motto is “No tricks. Just travel,” but this Halloween, we’ll let it be “No tricks. Just treats.” (Except we don’t really have a way to send you treats, just hotel rooms.)
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