In the spooky spirit of Halloween and its storied history steeped in ghosts, ghouls, and witchcraft, we looked to the traditions, festivals, travel experiences, and destinations that incite a little mystery and fantasy. From the home of the Salem Witch Trials to the inspiration for Dracula’s Transylvania home and castles with dark pasts, here are the spookiest travel experiences for Halloween.

Salem, Massachusetts

Whether or not you believe in witches, it cannot be denied that this New England town has a long storied history engrained in Wicca. During the late 1600s, Salem was home to many witch trials and anyone believed to be a witch was put to death. Today the town embraces its dark past with a month-long celebration of Halloween, called the Festival of the Dead. During October, more than 500,000 people flock to Salem, which normally has a population of 40,000 to immerse themselves in all manner of spooky experiences. Spend your days and the witching hour engaging in everything from a Psychic Fair to a Witchcraft Expo, visiting historical museums and spooky restaurants, exploring the witch trial tour, and dressing in your spookiest attire to attend the annual Salem Witches’ Ball at the Hawthorne Hotel.
Insider tip:  The Travel Curator visited Salem, during our road trip through New England and we can attest, there’s an undeniable eerie vibe to the place, go see for yourself.

Sleepy Hollow, New York

The legendary writer and historian, Washington Irving is credited with bringing the spook to Sleepy Hollow (even the name is spooky) when he set his iconic tale The Legend of Sleepy Hollow in this small town in Westchester Country east of the Hudson River.  Irvin is buried in the Sleepy Hollow Cemetery, which is a stop on the town’s Halloween Tour. The town is said to be haunted by the headless horseman, a character in Irvin’s book whose story begins when the Hessian trooper was decapitated during the Battle of White Plains in 1776 by an American cannonball. As the folklore goes, his comrades carried his body away but left his head on the battlefield, which rides around in search of at night, with Jack o’Lantern in his hand. If you’re a believer, you just might catch a glimpse of the headless horseman on Halloween Eve in Sleepy Hollow.  

Transylvania, Romania

Hoping for a chance encounter with Dracula? Head to Romania for an immersive historical trip inspired by Vlad the Impaler, the real-life Wallachian prince from the 1400s who is rumored to have been born in Transylvania. According to its horror-filled history, Vlad who lived in Transylvania’s Bran Castle once invited hundreds of people who didn’t obey his rule to a lavish banquet where he slaughtered them and impaled their bodies on spikes (hence his name). Set atop a winding mountain amid eerie clouds and fog the castle is the iconic setting for the 1897 Gothic horror novel Dracula by Bram Stoker. If that doesn’t make Transylvania one of the spookiest places in the world to visit, especially on All Hallows’ Eve, we don’t know what does. Like Salem, Transylvania embraces its dark past with Dracula-themed events and experiences aplenty. Visit “Dracula’s Castle” at Bran, stay at the Dracula Hotel on Borgo Pass, feast in one of the many Dracula-themed restaurants and take a midnight tour of the castle on Halloween to experience magic shows, check out the lavish costumes, and participate in a howling at the moon contest. In addition to all the spook, we’ve named Romania one of the most romantic cities in the world, especially for honeymooners. 

New Orleans, Louisiana

New Orleans, Louisiana is a beautiful fairytale city that is also high on the spooky list with a rich history of voodoo, vampires, above-ground tomb; think Vampire Diaries, True Blood, and American Horror Story. And, while there’s plenty of super spooky action for All Hallows’ Eve, there are also more traditional, non-horror celebrations and happenings in the iconic jazz and rhythm and blues city. On the standouts for Halloween is the famed multi-day music festival Voodoo Music + Arts Experience, where you can enjoy a diverse music line-up from Halloween-centric through to indie music, along with great food and art and culture-filled events.  Or head to Carousel Gardens Amusement Park and Storyland, to explore the pumpkin patch, go on a hayride and get your trick-or-treating on.  For the active, try your luck in the New Orleans Zombie Run, a 2-mile race through NOLA’s Warehouse District for which zombie make-up and costumes are a must. And for the ultimate scary Halloween experience, take a cemetery tour of the many above-ground tombs, or a ghost tour with French Quarter Phantom Tours to immerse yourself in historical sightings, modern paranormal themes, pop into Marie Laveau-inspired voodoo shop, and learn about the horrors of America’s first documented serial killer, Marie Delphine LaLaurie.

Chicago, Illinois

Image Courtesy of Open House Chicago

Chicago’s tainted past – fires, serial killers, and deep-rooted mob history – has fuelled its reputation as one of the spookiest cities to visit on Halloween.  To immerse yourself in The Windy City’s dark side, visit the Nederlander Theater, which was the site of a 1903 fire at the then-named Iroquois Theater, thought to still be haunted by the ghosts of those who died. Or check out the former site of “Murder Castle”, which was the home of H.H. Holmes, a doctor, and pharmacist with a bloodthirsty obsession with death who is widely considered to be the country’s first serial killer. Holmes is believed to have murdered around 200 women, who he lured to work or stay at his hotel-style castle, during his 1891 – 1894 reign of terror.  Holmes was hanged in 1891 and the castle was remodeled as an eerie attraction known as “Holmes Horror Castle”, but it burned to the ground before it opened.  The site is now occupied by the Englewood branch of the U.S. Post Office and reports of paranormal activity there abound. 

Edinburgh, Scotland

Scotland has an interesting take on Halloween, instead of leaning into horror stories, they look to the pagan religious festival of Samhain, which originated from an ancient Celtic spiritual tradition that they consider is how Halloween came about. Intended to mark the seasonal transition from summer to winter (light to dark) and celebrate the harvest, according to folklore during the festival, the barriers between the physical world and spirit break down allowing humans to interact with the other world.  Celebrated annually in Edinburgh over Halloween, the Samhain Fire Festival is an immersive, cultural event that explores the opposing forces and demons of Halloween through theatre performances, dazzling fire shows, drumming, and costume parades.  Beyond the festival, there are plenty of other spooky experiences and incredible castles all with their own stories, on offer in the richly historic city of Edinburgh. Spend an evening exploring the Blair Street Underground Vaults, widely reported to be haunted and awash with paranormal activity.  Run through the labyrinth of stone tunnels lit only by candlelight, to see where criminals were once tortured and executed, and meet ghosts and ghouls along the way.