'Dracula's Castle', Bran Castle, Transylvania, Romania.

As October approaches, All Hallow’s Eve enthusiasts begin searching for the unique thrills and chills that accompany the year’s spookiest season. Eerie-loving adventurers who are seriously into Halloween may wish to celebrate by spending more than one night immersed in the real-life places of inspiration for some of the most iconic terrors associated with the holiday.

For an overview of Halloween-themed offerings, we looked to Stride, which is backed by JetBlue and purports to be the first comprehensive online marketplace for experiential, multi-day, multi-destination travel packages. Guests can find group tours organized by region, style, area of interest, age range, themes or opt for a tailor-made itinerary.

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Halloween in Transylvania

Synonymous with the ‘Dracula’ mythology, the very name of the place sends chills up your spine. Imagine spending your Halloween at a special, invite-only costume party, held in an authentic Gothic castle; and exploring the ruins of Bran Castle, the real-world ‘Dracula’s Castle’, rumored to be one of the most haunted places in all of Europe, with the Halloween in Transylvania tour from G Adventures.

You’ll explore Romania’s Medieval towns, and the Old-World cities of Bran and the country’s capital of Bucharest. En route to Bran, you’ll stop at the Rupea citadel, a fourteenth-century fortress, and discover nearby Brasov to observe the quaint hamlet’s Baroque architecture and Town Square.

Also along the way, you’ll see monasteries, museums, and beautiful, Old-German villages. Take a tour of old town Sighisoara and learn the birth story of Vlad “The Impaler”; and visit Casa Dracula—Vlad’s original home, which has been transformed into a restaurant that serves regional specialties.

Before departing from Bucharest at the end of your seven-day journey, explore the capital’s many attractions, visit the beguiling Museum of the Romanian Peasant, or soak in the sights of the city’s magnificent cathedral and Soviet-esque architecture.

Bran Castle in Transylvania, Romania. Better known as 'Dracula's Castle'.

Ireland’s Haunted Castles

Embark on an eight-night Haunted Ireland Castle Tour to witness firsthand the most ghostly buildings, ruins and landscapes of the Emerald Isle, where a long history of folkloric beliefs surrounding native spirits and elementals inspires tales in just about every location. Join the Haunted History Walking Tour of Dublin, where you’ll discover eerie, cobblestoned lanes and listen to stories from the city’s underbelly.

You’ll visit various haunted places across Counties Monaghan, Armagh and Meath, take a guided tour of The Haunted Bog Road in Connemara, see the breathtaking spectacle of Kylemore Abbey and its Victorian Walled Gardens, unravel the ancient mysteries of Loughcrew Megalithic Cairns—a series of hilltop, mounded tombs that date back to the fourth millennium BCE—and much more. Along the way, you’ll have the opportunity to stay in some of the country’s most magnificent castles.

Kylemore Abbey, Ireland.

Halloween in America

Explore America’s haunted history, and most macabre myths and legends on a Halloween in America itinerary. Begin in Boston and head to historic Salem, Massachusetts, site of the infamous Salem Witch Trials of 1692, visit the Witch Museum, Witch House, and Witch Memorial, and see Nathaniel Hawthorne’s House of the Seven Gables.

Get the chills in one of the Haunted Happenings Carnival’s many haunted houses, carve your own jack-o-lantern and get lost in a corn maze. In Boston, the Ghosts and Gravestones Haunted Cemetery tour takes guests on a walk among the dead within 400-year-old burying grounds, telling tales of the sordid practices of the past.

Philipsburg Manor in Sleepy Hollow, New York.

Embark on a lantern-led ghost tour through the shadowy lanes of Newport, Rhode Island before journeying on to see Sleepy Hollow, New York, the scene of Washington Irving’s famous fictional work.

There, you’ll be led through a gothic castle and gardens by morbid characters at Jay Ghoul’s House of Curiosities and, hopefully, view the highly popular Great Jack O’Lantern Blaze along the river.