Tombstones and gravesite at Bonaventure Cemetery, Savannah, Georgia.
Trip Ideas

The Spookiest Cities in the U.S. To Celebrate Halloween

With Halloween just around the corner, we suggest celebrating the season in the most Jetsetter way possible—with a trip. Though you'll likely find spooky fun in any city, it’s worth getting away to experience even more unique fun-and-fright-filled celebrations. Whether you’re looking for a full-on scare or just some costumed craziness, below are our picks for the best cities in the U.S. to celebrate Halloween.

1

Hudson Valley, NY

Hudson Valley is the home of Sleepy Hollow, the storied setting of the namesake tale by Washington Irving, who is buried in the village’s cemetery. Watch the legend come to life at Philipsburg Manor, where the Horseman’s Hollow haunted trail and house are open all month long. If The Legend of Sleepy Hollow is too dark for your taste, enjoy the lighter side of Halloween at The Great Jack O’Lantern Blaze, the tri-state area’s biggest fall event. There, more than 7,000 illuminated pumpkins at Croton-on-Hudson’s Van Cortlandt Manor are on display throughout the rest of the month and November.

Book Hotels in the Hudson Valley

2

San Jose, CA

San Jose’s Winchester Mystery House is one of America’s most legendary haunted mansions, so it only makes sense to experience it by candlelight on Halloween. Debuting an all-new show this fall, the Hallowe’en Candlelight Tour features a maddening maze and promises lots of scares. Even if you’re not a big believer in the house's haunts, it’s still worth a visit to see its old-world architecture and learn about its captivating history. The mysterious house was once the personal residence of a wealthy widow named Sarah Winchester, who bought it as an eight-room farmhouse and renovated it continuously for decades, beginning in 1886. By the time Winchester died in 1922, the sprawling mansion had 160 rooms over 24,000 square feet—built at a price tag of $71 million in today’s dollars.

Book Hotels in San Jose

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3

Salem, MA

The witchy town of Salem (just 16 miles north of Boston) is ripe with Halloween offerings, from the kid-friendly Carnival to the Haunted Magic Show to the Halloween Ball with the Witches of Salem. Of course, there are also endless tours, museums, and heritage sites to check out; the town’s infamous history as the site of the Witch Trials of 1692 makes for lots of learning and educational opportunities. For an extra dose of magic, check out the Psychic Fair and Witches’ Market, where you can get tarot card and palm readings or pick up some crystals and spell kits as souvenirs. No matter what activities you fill your time with, a day trip or overnight stay in “The Witch City” will make for a memorable Halloween.

RELATED: The Scariest Places in the World (It’s Almost Halloween, People!)

Book Hotels in Salem

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4

West Hollywood, CA

Each year, half a million people make their way to West Hollywood’s Halloween Carnaval, one of the biggest, rowdiest, and most risqué Halloween celebrations around the country (read: best leave the kids at home). This October 31st street party is not your typical parade: instead, you'll find people dancing, walking around, and popping into nearby bars as they please, with multiple music stages blasting live sets along Santa Monica Boulevard. There’s also an official naming ceremony for Queen of The Carnaval (past recipients include Rihanna and Queen Latifah). Costumes are typically elaborate and cheeky, so come prepared and expect to be wowed.

Book Hotels in West Hollywood

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5

Savannah, GA

Considered one of the most haunted cities in the nation, Savannah is teeming with storied sites popular among paranormal enthusiasts. From ghost-ridden hotels (like the circa-1851 Marshall House and the historic district’s Hamilton Turner Inn) to eerie hubs like Madison Square and Factor’s Walk, the city is chock-full of spooky landmarks to view on a Halloween ghost tour. If you finish the tour unscathed and want more, dive in with a late-night guided paranormal investigation at the Sorrel Weed Mansion, known as the most haunted spot in town.

Book Hotels in Savannah

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6

New Orleans, LA

The annual Voodoo Music + Arts Festival is proof enough that NOLA goes hard during Halloween weekend. With a lineup that includes Mumford & Sons, Odesza, Arctic Monkeys, and Modest Mouse, plus large-scale art installations and an amazing culinary experience, it’s no wonder the three-day event has drawn over a million people throughout the years. Is a Halloween music festival not really up your alley? You’ll still be able to find plenty of other activities to keep you busy. Prepare to scream at the infamous Mortuary Haunted House all week long, or put on your best dress for the Victorian-themed Endless Night Vampire Ball on October 27.

RELATED: The Best Fall Weekend Trips to Take with a Significant Other

Book Hotels in New Orleans

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7

New York City, NY

Though you’re guaranteed to never face boredom any time of year in New York, the city bumps it up a notch for Halloween. If you’re into the classics, you can’t go wrong with the Village Halloween Parade: all you have to do is show up in costume to join the event yourself, or you can watch the wild creativity from the streets. For a real scare, check out one of the many haunted houses or ghost tours around the city. Just want to dance the night away? There are literally hundreds of clubs, bars, and Halloween-themed events that go all out for the weekend; we recommend Inferno after an immersive theatrical experience at the Sleep No More show at the McKittrick Hotel.

Book Hotels in New York City

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