5 Spooky Halloween Vacations for Families: Salem, Sleepy Hollow, and More

Scare up some fall fun on these Halloween vacations for families.
Lighting of the Great Pumpkin in St. Helens, Oregon (Photo: City of St Helens)
St. Helens, Oregon (Photo: City of St Helens)

With school back in swing and the holidays just around the corner, fall vacations may not be top of mind for most families. But the spooky season’s sweet combination of crisp weather and great travel deals actually makes it the perfect time to squeeze in a family trip. And while September and November both have their charms, for Halloween fans like me there’s no better time to travel than October. 

Maybe that’s because I grew up near Salem, Massachusetts, a city that really knows how to celebrate the season. (My novel, The Witches of Willow Cove, was inspired by a lifetime of Salem Halloweens.) Maybe it’s because everywhere feels just a little bit spookier when the air gets chilly and the nights grow longer. Whatever the reason, October always puts me in the mood for ghostly fun—especially when I’m traveling.

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Thankfully for Halloween lovers, there’s no shortage of places across the country that go all out for Halloween. Here are the best destinations for family-friendly Halloween vacations around the country.

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1. Salem, Massachusetts

Haunted Happenings parade in Salem, Massachusetts (Photo: John Andrews)
Salem, Massachusetts, is the ultimate Halloween vacation destination (Photo: John Andrews)

With a year-round tourist industry built around the infamous Salem Witch Trials, the Witch City celebrates all things mystical and magical 365 days a year. Can’t-miss year-round attractions include the Salem Witch Museum, Salem Witch Dungeon, and Salem Pioneer Village. But Salem definitely raises its game for Halloween vacations when fall rolls around. Its annual Halloween celebration, now in its 40th year, is the biggest in the world, spawning parades, parties, ghost tours, haunted houses, museum displays, Hocus Pocus recreations, and other eerie events across the city throughout the month of October. 

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The city swells with tourists in the fall, but that’s what gives Salem its forever-Halloween vibe. Check the city’s Haunted Happenings calendar for events and activities throughout the season, and don’t be afraid to venture beyond Salem for Halloween fun, too. Corn mazes, hayrides, apple picking, and other fun family activities abound all across New England in the fall.

2. Sleepy Hollow, New York

Sleepy Hollow Cemetery in Sleepy Hollow, New York (Photo: Shutterstock)
Sleepy Hollow in New York’s Hudson Valley was made famous by Washington Irving’s fictional Headless Horseman (Photo: Shutterstock)

When the leaves begin to turn, the real-life town made famous by Washington Irving’s fictional Headless Horseman becomes a mid-Atlantic fall getaway destination unlike any other. Families come to Sleepy Hollow and the Hudson Valley from far and wide for Halloween vacations that include haunted hayrides, cemetery tours, gothic mansions, and costumed 5k runs.

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In nearby Croton-on-Hudson, the annual Great Jack o’Lantern Blaze showcases more than 7,000 hand-carved pumpkins. The after dark illumination utilizes synchronized lightning set to an original soundtrack for an extra dose of spooky chills. 

3. Anoka, Minnesota

It takes a special kind of city to call itself the Halloween Capital of the World, but Anoka earned its title more than 100 years ago by being the first in the nation to put on a giant Halloween celebration on October 31. 

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These days, Halloween in this riverfront city about 30 minutes from Minneapolis means ghost tours, scarecrow contests, pumpkin weigh-offs, outdoor movie nights, a house decorating contest, 5k ghost run, illuminated nighttime parade, and the daytime Grande Day parade (the largest in the state).  

4. St. Helens, Oregon

Spirit of Halloweentown in St. Helens, Oregon (Photo: City of St. Helens)
St. Helens, Oregon, is the real-life backdrop for the Disney movie Halloweentown (Photo: City of St. Helens)

For people of a certain age, Disney Channel’s 1998 movie Halloweentown is Halloween. And the real-life Oregon town where Halloweentown was filmed—St. Helens, not far from Portland—embraces that movie magic with its Spirit of Halloweentown celebration each year. 

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Come October, the small city attracts legions of Halloween-loving families to its Riverfront District, which is transformed into the Spirit of Halloweentown with the lighting of the Great Pumpkin. There are costume contests, haunted tours, parades, and all manner of creepy scarecrows throughout the month. Most of the action takes place on the weekends, but the Halloweentown vibe is strong every day of October. 

5. Orlando, Florida

Halloween at Magic Kingdom in Orlando (Photo: Courtney Keifer)
Orlando goes all in on Halloween vacations at its many theme parks (Photo: Courtney Keifer)

Florida’s theme park capital gets into the spirit of Halloween early with festivities kicking off in August each year. Mickey’s Not-So-Scary Halloween Party at Walt Disney World (for all ages) and Halloween Horror Nights (for teens and adults) at Universal Studios Florida are the headline attractions for Halloween vacations, but SeaWorld, LEGOLAND, and the other Orlando theme parks also get in on the action with spooky events throughout the season.

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Like most Halloween destinations, tickets to the Halloween events at Disney and Universal tend to go quickly and need to be purchased well ahead of time. Even if you’re not an advance-planner, though, you can still enjoy the season just by visiting the parks when they’re all decked out for Halloween. 

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Recognized with multiple awards for excellence in travel journalism, Josh Roberts has more than two decades of experience helping travelers discover where to go and what to do when they get there. He is the former Senior Executive Editor of Tripadvisor's SmarterTravel, Airfarewatchdog, and FamilyVacationCritic websites, and the co-founder and Editorial Director at FamilyVacationist.

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