Best Upstate New York Halloween Getaways

Within a few hours of well-lit Manhattan, the dark dreary forests, fog-shrouded bogs and upstate New York Halloween haunts come to life for spooky autumn thrills. Explore the tranquil region along the Hudson River and move farther upstate through Westchester, Dutchess, Orange and Ulster Counties.

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Halloween is a great time of year to celebrate the dead and undead.

It is bursting with fun and safe, wear-your-own-mask events and attractions themed to the holiday.

Do it live, virtually, or go for a more fearful celebration. New York state has a frightening Halloween weekend getaway option for everyone. And New York state is not alone; for more haunted house options, visit our Haunted House and Halloween Weekend Breaks Directory.

Staying Safe on Upstate New York Halloween Getaways

Montage of guest rooms, haunted hallways and the outside of haunted Shanley Hotel, Catskills, New York.
A montage of guest rooms, haunted stairways and halls at the haunted Shanley Hotel, Catskills, New York. Photo c. Shanley Hotel.

First, know that if you’re up for a road trip from New Jersey, Pennsylvania or Connecticut, the entire state of New York has a Haunted History Trail featuring 88 of the sickest attractions on a tour across the state. The trail is open year round and gets extra traffic during October. Enjoy the fun, festive occasion for its pumpkins, candy and costumes if the scary stuff doesn’t appeal.

Or, celebrate the Halloween holiday with a one or two-night travel package (no one lasts longer than that.) The Shanley Hotel, for example, in the Catskills, promises muffled screams, the tinkling of a remote piano, shuffling feet and other far-off sounds to lull you to sleep. Should be a howling fun time.

Finding New York Halloween Fun

Carved pumpkins make a Pumpkin Zee Bridge at Cortland Manor's Blaze event.
Pumpkin Zee Bridge at Cortland Manor’s Blaze event.

Like everything else, when demanding New Yorkers want a haunted house, they want a good haunted house. Forget about Manhattan, where scary things happen all the time. If your kids and teens want a candy-collecting weekend away, with a fun, scary haunted house, a real haunted house, or a haunted house tour, an upstate New York Halloween can supply it.

Need a cheap rental car for an upstate New York Halloween?

From Tarrytown to Woodstock to New Paltz, there are lots of other autumn attractions for all ages. Your New York Halloween getaways should include hayrides, museums, nature hikes, leaf peeking, corn mazes, PYO apple and pumpkin farms and much, much more. Try the toddler-friendly Halloween thrills of LEGOLAND New York’s Brick-or-Treat Trail each fall.

Once you’ve spooked yourself to tears, you can calm down at one of the region’s many hotels. Search for fall getaway packages that include breakfast and Wi-Fi with a double room, as well as local shuttles for the car-less. The Westchester County Tourism Office has a listing of what’s available.

Low Freak Out Factor: Hudson Valley’s Great Jack O’Lantern Blaze

A steam train made out of pumpkins is only treat at the Great Jack O'Lantern Blaze
A steam train made out of pumpkins is only treat at the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson. (Photo by Tom Nycz)

The Great Jack O’Lantern Blaze at Van Cortland Manor is Hudson Valley’s biggest Halloween event, taking place Sept. 16 – Nov. 20 (November weekends). Note that timed entry tickets are required to limit the number of participants and maintain social distancing between families and groups.

Visitors get to experience the sight of over 7,000 hand-carved jack o’ lanterns and wander through the historic property which is all decked-out for Halloween. In past years, the pumpkins have been astonishing: dinosaurs roam the earth and pirates set sail for buried treasure along Pumpkin Promenade and giant spiders create monstrous webs. Snakes, sea creatures and ghosts entwined in special lighting, effects and haunting music have entertained visitors. Visit Jack O’ Lantern Blaze. If they are sold out, there’s still a possibility that local hotels featured on their website have tickets if you book a room with them.

Note that Philipsburg Manor in Tarrytown, after several months of pandemic closure, has reopened for walking tours, weekends only.

Forget pumpkins! Want to get into the Big Apple for Halloween in New York City? Here’s where to go and what to see.

And the Real Sleepy Hollow Is?

Actor in costume holds up a staff and carved pumpkin at Washington Irving's Legends show at Sunnyside, Tarrytown, New York.
Master storyteller Jonathan Kruk performs “Washington Irving’s Legends” show each fall at Sunnyside in Tarrytown, New York. Photo c. HudsonValley.org

You must get everyone psyched by reading Washington Irving’s “Legend of Sleepy Hollow.” This classic tale introduced characters like the Headless Horseman and Ichabod Crane to the world in 1820. It all happened in Tarrytown. At Sunnyside, the author’s estate, every weekend from mid-September to mid-November comes to life with master storyteller Jonathan Kruk reciting sections of the book for fans old and new.

Tour Sleepy Hollow, Westchester County’s actual village of the same name, and drop in (or drop out) at the famous, 85-acre Sleepy Hollow Cemetery. It’s known for burying the very rich and very famous, including beauty magnate Elizabeth Arden; NY Public Library benefactors Brooke Astor and Andrew Carnegie; car scion Walter Chrysler and his later nemesis, labor leader and AF of L founder Samuel Gompers and local baron William Rockefeller.

Yes, the author of “Legend of Sleepy Hollow” –Washington Irving himself — is buried there too. There are limited day and evening guided tours, operating by reservation only. There are several scandal-full storytelling tours (some not advisable for kids). Older kids and their parents will appreciate the evening lantern strolls.

Orange County Has High Freak Out Hauntings

What about Pure Terror Screampark? See for yourself that it holds the Guiness Book of Records title for longest walk-through haunted attraction. That means a lot of walking! Regardless of your appetite for risk, Screampark is open weekends by advanced reservation, from late September to Halloween. Honestly, images of “The Crypt” and “The Coven,” among their 10 haunted houses, made us jump when their website loaded. This Catskills scare-atorium has separately themed fright zones, including our favorite “Pure Darkness.”

By the way, their website says you cannot carry babies through the exhibits, nor are exhibits recommended for pregnant women. Hmm. Located at 1010 State Route 17M, Monroe, NY 10950 in who-knows-where Orange County, it is just 3 miles from the Woodbury Commons shopping outlet, where you can really freak out spending money.

Upstate New York Halloween Headless Horseman Attraction

The Pumpkin Trail at Headless Horseman in Ulster County. Photo c. Haunted America

When it comes to New York Halloween scares, however, farther north in Ulster is the place to be. Do you want to scream all night or just enjoy some Halloween activities? The Headless Horseman at 778 Broadway, Route 9W in Ulster Park, NY 12487, has been named the #1 Haunted Attraction in the country by Hauntworld.com. Headless Horseman Haunted Attractions is a unique experience, celebrating their 30th anniversary this season. This year’s “Night of The Shadows” theme features a theatrical walk-through and nine additional haunted attractions. Immerse yourselves with stunt performers, trained actors, monsters, pyrotechnics, professional illusions, and a cast and crew of over 300.

Look for ghoulish performers and plenty of shops for candied apples, scary gifts and yummy pumpkin pie. Little ones have two mildly terrifying October dates dedicated just to “Children’s Day.”

It’s Less Scary in New Paltz for an upstate New York Halloween

The Horseman’s Tomb at Headless Horseman in Ulster County. Photo c. Haunted America

The city of New Paltz turns a bit scary, too. And we don’t mean how spooky the old Mohonk Mountain House looks under a full moon.

Not only are the leaves gorgeous during autumn for the upstate New York Halloween celebration, but there are also plenty of other family-friendly activities. Kelder’s Farm has a 100-acre Pick-Your-Own field with pumpkins and a corn maze that everyone can get lost in. The farm is open daily for pumpkin, sweet corn and squash picking (apples are mostly gone by Halloween); mini-golf, a jumping pillow and other seasonal fun. Masks and social distancing are required. Fall Harvest Days take place Saturdays until Halloween.

Ulster County hosts animal sanctuaries where you can learn how to protect animals. The Woodstock Farm Animal Sanctuary, for example, offers an educational experience on how to help our furry friends and our environment. They also have a five-bedroom Gray Barn open for weekly rentals all season so you can work and learn remotely in a very pastoral setting. Another lodging option is the Emerson Resort & Spa, a rural upstate New York Halloween getaway that hosts a famous kaleidoscope and lots of fun family activities and adventures. Note, it’s only open Thursday through Monday (daily over the holidays) and is offering 30% discounts on two-night stays.

Adirondacks Boasts a Ghostly Lake

Pulpit Rock on Lake Placid
Pulpit Rock on Lake Placid doesn’t look like a burial place (until Halloween!)

How far north will you go for a scary upstate New York Halloween?

When Mabel Smith Douglass disappeared on Lake Placid in 1933, no one knew she would become a Halloween tourist attraction. The story goes that the former dean of Rutger’s Womens College disappeared while rowing on the lake near to an outcropping known as Pulpit Rock. Her corpse, perfectly preserved and with an anchor line around her neck, was found 30 years later by scuba divers. Today you can take a boat tour of the site and hear more details. And, admire the fall foliage. It’s said that campers and boaters have reported seeing a ghostly figure of a woman hovering near Pulpit Rock. These sightings keep the legend of “the Lady in the Lake” alive to this day.

Pretty Whiteface Lodge is a very luxurious, new classic resort modeled after the Adirondacks Great Camps. They welcome families to leaf peep while enjoying a myriad of treats around the charming town of Lake Placid. Swim in their indoor/outdoor heated pool. Knock down a few pins in their two-lane bowling alley. Hit a few rounds of mingolf. Catch a flick in their in-house cinema. Slow down on the candy while enjoying S’mores by the outdoor firepits or the lodge breakfast — it’s included in rates.

Trick or treat anyone? Get haunted house for kids options, Halloween fun and more by visiting our Haunted House and Halloween Weekend Breaks Directory.

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3 Replies to “Upstate New York Halloween Getaways”

  • Devesh

    Nice post.
    Thanks for sharing your wonderful experience with us. Loved your blog!

  • Marialejandra Garcia Palma

    Stay at Castle Hotel and Spa and treat yourself to a Thai-inspired spa that is great for pampering or a romantic activity for couples.

  • Ghana

    Rockefeller State Park offers seasonal activities including hiking, running, bird-watching, fishing ( New York state fishing license required), picnicking, horseback-riding, carriage-driving, photography, painting, and geocaching (park permit required). Sleepy Hollow and neighboring Tarrytown have a deep immigrant history resulting in a rich mix of cuisines: Italian, Greek, Mexican, Indian, French, Portuguese, Irish, Japanese, Dominican, Chinese, Ecuadorian, Thai, Moroccan, and Chilean. Foodies should not miss the Tarrytown and Sleepy Hollow farmers market at Patriots Park where you ll find fresh Hudson Valley produce, meat, bread, and wine.

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