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Best Halloween Events in Westchester and the Hudson Valley for Kids and Families

Legoland New York is all decked out for the Halloween season. Photo courtesy of Legoland
Legoland New York is all decked out for the Halloween season. Photo courtesy of Legoland
9/24/23 - By Katherine Dhurandhar

Spooky season is here, and there’s no shortage of great Halloween events in Westchester and the Hudson Valley. Whether you have thrill-seeking teens or pumpkin-loving toddlers, we’ve got plenty of options for your brood. 

Sleepy Hollow and Tarrytown are prime Halloween destinations owing to their pride in being the home of Washington Irving and the setting of his famed The Legend of Sleepy Hollow. Throughout the region, haunted attractions abound for the older set, including a forest trail at a historic haunted hotel, while little ones can delight in friendly fun like Monster Mash-inspired brick-or-treating at Legoland New York or a visit with costumed alpacas. Meanwhile, the whole family can enjoy the new Pumpkin World attraction in Rockland, as well as Westchester's most celebrated Halloween event, the Great Jack-o'-Lantern Blaze.

Read on for our list of the best Halloween events in Westchester and nearby. To get the most out of this fun season, turn to our Halloween Fun Guide, which includes recommendations for top local corn mazes, pumpkin patches near Westchester, at-home Halloween activities, and much more. You’ll also find many more Halloween events on our Family Activity Calendar, with new ones added frequently.

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Best Halloween Events in Westchester

Home of the "Legend"

Irvington
Friday-Sunday from September 15 through November 15, plus Columbus Day and October 30 and 31, 2023
A Halloween tradition returns, offering daytime holiday fun for all ages. Take a tour of the first floor of Washington Irving's historic home, view an exhibit about his tale "The Legend of Sleepy Hollow," enjoy a short shadow-puppet film, and play games on the lawn. READ MORE

The Great Jack-o'-Lantern Blaze

Croton-on-Hudson
Multiple dates through November 19, 2023
This renowned walk-through Halloween experience features more than 7,000 hand-carved, illuminated jack-o'-lanterns forming assorted impressive displays, with lighting and music enhancements. See the pumpkin carousel, windmill, and the New York City skyline. New for 2023, see an animated Ferris wheel and a jack-o'-lantern ode to circus sideshows. READ MORE

The Spirits of Sleepy Hollow Country: A Night of Legendary Magic

Sleepy Hollow
Fridays through Sundays, September 29-October 29, 2023
Master illusionists take the audience on a journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings leave guests spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda, Major Andre, and the Headless Horseman himself! READ MORE

Classic Evening Lantern Tour at Sleepy Hollow Cemetery

Sleepy Hollow
Fridays-Sundays in September and daily in October, plus Halloween and select dates in November, 2023
Halloween season is a fitting time for a guided tour of the historic Sleepy Hollow Cemetery, the resting place of the author of "The Legend of Sleepy Hollow." Opt for a daytime tour or a nighttime tour lit by kerosene lamps.  READ MORE

Tarrytown Halloween Parade

Tarrytown–FREE
Saturday, October 28, 2023
This spooky spectacle of marchers and floats is back in 2023 with costume and float-decorating contests. The parade begins in Patriot Park and ends at Main Street with a block party.  READ MORE

Halloween Weekend at the Museum

Rye–FREE with museum admission
Saturday, October 28-Sunday, October 29, 2023
Swing by the Westchester Children's Museum all Halloween weekend for Halloween-themed STEAM activities, including name 'dem bones, a glow-in-the-dark room, spider web engineering, ghost pour painting, and monster hide n' seek. Get dressed in your best costume and join all the fun.     READ MORE
Wander through the I Spy Halloween Nature Trail at Hudson Highlands Nature Museum. Photo courtesy of the museum
Wander through the I Spy Halloween Nature Trail at Hudson Highlands Nature Museum. Photo courtesy of the museum

Best Halloween Haunted Houses and Trunk-or-Treats in Orange County

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Saturdays and Sundays, September 16-October 29, 2023
Legoland New York goes all-out for Halloween, with costume contests, dance parties, live entertainment, characters, and trick-or-treating. The event is included with the price of admission. READ MORE

Pure Terror Scream Park

Monroe
Fridays-Sundays, September 23-October 29, 2023
An extensive Halloween attraction, Pure Terror features 10 haunted houses, including the new Woods of the Dead. The walk-through experience utilizes costumed actors, special effects, and elaborate sets on a theatrical scale. Stop in the midway for food and music. New for 2023: Jungle Rot, Pumpkin Alley, and Monster Midway.    READ MORE

"I Spy" Halloween Nature Trail

Cornwall
Saturday, October 28, 2023
Families looking for a fun but not-so-spooky Halloween adventure can drop in on the annual "I Spy" Halloween Nature Trail. Find objects cleverly hidden along your self-guided adventure to earn a prize upon completion. Costumes encouraged. READ MORE

The Sugar Loaf Halloween Festival

Chester
Saturday, October 28, 2023
This festival kicks off with a trunk-or-treat that's followed by music, a jack o' lantern contest, a witches meet-and-greet, a Halloween costume parade, and more. There will also be a vendor village and fall treats like cider and donuts.  READ MORE

Braeside Camp Trunk-or-Treat

Middletown–FREE
Sunday, October 29, 2023
This second annual trunk-or-treat also features a pumpkin-carving contest, costume contest, haunted house, and art craft. From 7pm to 10pm, there is a haunted house fundraiser for kids 10 and up.   READ MORE
Spend a not too spooky day at Children's Day at Headless Horseman Hayrides in Ulster. Photo courtesy of the events
Spend a not too spooky day at Children's Day at Headless Horseman Hayrides in Ulster. Photo courtesy of the events

Top Halloween Festivals and Haunted Houses in Ulster County

Headless Horseman Haunted Houses

Ulster Park
Fridays through Sundays, October 6-29, 2023, plus Saturdays, September 23 and 30
Not for the faint of heart, this seasonal attraction pulls out all the stops to put the fright in Halloween. This year's format is a walk-through experience where horror-seekers encounter assorted settings like haunted hotels, a corn maze, and a greenhouse. A separate ticket gives access to an escape room. READ MORE

Children's Day at Headless Horseman Hayrides

Ulster Park
Saturdays, October 7 & 21, 2023
On Children's Day, this hayride tones down the scare level. Music and other surprises make this the perfect outing for families with young children. READ MORE

MyKingstonKids Halloween Fest & Parade

Kingston–FREE
Saturday, October 28, 2023
Back for its sixth year, the annual MyKingstonKids Halloween Parade & Festival is one of Kingston's biggest kids' parties. After the parade comes the festival, which features special Halloween performances including singers, costumes, various types of music, magic, lots of dancing, and more.  READ MORE

Halloween at Ashokan Center

Olivebridge
Sunday, October 29, 2023
Put on your costume early and explore the campus at Ashokan Center this Halloween. Enjoy a spooky and historic scavenger hunt, live entertainment, and a costume contest! Hot chili, chips, hot cider, and cookies are available for purchase. Admission includes Halloween candy. READ MORE

Walker Valley's 10th Annual Trunk-or-Treat

Pine Bush–FREE
Sunday, October 29, 2023
The Walker Valley/Town of Shawangunk's 10th annual trunk-or-treat includes live music, a haunted house for the little ones, craft & food vendors, and of course tons of trunks with TONS of candy. Kids can check out the big fire truck and enter the costume contest.  READ MORE
Keven McCurdy's Haunted Mansion is a theatrical walk-through experience featuring assorted creepy scenarios that pile on the Halloween spook. Photo courtesy of Kevin McCurdy's
Keven McCurdy's Haunted Mansion is a theatrical walk-through experience featuring assorted creepy scenarios that pile on the Halloween spook. Photo courtesy of Kevin McCurdy's

Best Halloween Events and Trunk-or-Treats in Dutchess County

Kevin McCurdy's Haunted Mansion

Wappingers Falls
Fridays-Sundays, September 30-October 28, also October 30 and 31, 2023
Opening for its 47th season, this theatrical walk-through experience features assorted creepy scenarios that pile on the Halloween spook. Beware the Wicked Woods Bedtime Stories, The Procedure (the doctor is in...), and other frights. Special effects, projections, and other elements embellish the mood. READ MORE

A Very Fluffy Halloween

Pleasant Valley
Weekends, October 14-Sunday, October 29, 2023 plus on Friday, October 27 and Halloween
It’s a Halloween fest – only way cuter. Enjoy this fun guided farm tour that lets you meet the animals of Lilymoore Farm and Dreaming of A Chance pigeon sanctuary. Join the alpacas and goats by wearing your best costumes! READ MORE

The Hudson Valley's Best Trunk-or-Treat

Beacon & Hopewell Junction–FREE
Saturdays, October 14 & 28, 2023
This trunk-or-treat event takes place on two dates at two different locations. The event is 100% outdoors and includes trunk-or-treating, a bounce castle, games, and dancing. There are also awesome vendors for you to shop with. READ MORE

Halloween Spooktacular at Mid-Hudson Discovery Museum

Poughkeepsie
Friday, October 27, 2023
Enjoy some not-so-scary fun at this Halloween Spooktacular Party! The museum will be decked out with fun and spooky decorations, with Halloween-themed exhibits, a mysterious haunted house, and creepy science experiments. There will also be trick or treating, a costume parade, and more. READ MORE

Annual Roller Magic Halloween Party

Hyde Park
Saturday, October 28, 2023
Hyde Park Roller Magic invites guests to come out and skate in costume this Halloween weekend with games, prizes, treats, and a costume contest. READ MORE
Enjoy an illuminated wonderland of hand-carved Jack O’Lanterns and fall festivities. at Pumpkin World in Pomona. Photo courtesy of Pumpkin World
Enjoy an illuminated wonderland of hand-carved Jack O’Lanterns and fall festivities. at Pumpkin World in Pomona. Photo courtesy of Pumpkin World

Best Halloween and Trick-or-Treat Events in Rockland County

Pumpkin World

Pomona
Wednesdays-Sundays, September 29-October 29, 2023, plus October 30 and 31
Pumpkin World is an interactive family-friendly fall extravaganza featuring a 45-minute jack-o'-lantern trail illuminated with intricately hand-carved pumpkin art sculptures. The festival also includes a whimsical Pumpkin Village offering more fall fun for the whole family to enjoy with music, games, merchandise, and thrilling pumpkin-carving competitions by master artists. READ MORE

Nyack Halloween Parade

Nyack–FREE
Saturday, October 28, 2023
Put on your best costume and come out for one of the biggest Halloween parades in the area. The parade moves through downtown Nyack with float contests and costume contests for kids and adults.  READ MORE

Boo at the Bear Mountain Zoo

Bear Mountain
Saturday, October 28, 2023
Head to Bear Mountain Trailside Museums and Zoo for a spooky good time. Make Halloween snacks for the bears and watch them chow down. Family-friendly activities include pumpkin decorating, matching games, and crafts. Wear your favorite not-so-spooky Halloween costume! READ MORE

Trick or Treat at the Palisades

Nyack–FREE
Saturday, October 28, 2023
Join ForTheCulture Foundation for its annual Halloween trick-or-treat event, where children can trick or treat from one decorated table to the next, with music, entertainment, and more.  READ MORE
Wind through our garden trails marvel at thousands of unique hand-carved jack-o-lanterns and glowing pumpkin art at Peace, Love and Pumpkins. Photo courtesy of Bethel Woods Center for the Arts
Wind through our garden trails marvel at thousands of unique hand-carved jack-o-lanterns and glowing pumpkin art at Peace, Love and Pumpkins. Photo courtesy of Bethel Woods Center for the Arts

Awesome Halloween Festivals and Events in Sullivan County

Peace, Love & Pumpkins

Bethel
Friday, October 13-Sunday, October 29, 2023
View hand-carved jack-o'-lanterns and glowing pumpkin art as you walk the garden trails on the site of the Woodstock Festival. Exhibits include mermaids, dinosaurs, and Woodstock Festival icons. READ MORE

Dark Forest Fright Walk at Burn Brae Mansion

Glen Spey
Fridays and Saturdays, October 13-28, 2023
Dare to take a walk through the haunted forest at the historic Burn Brae Mansion, a historic haunted location, and encounter the creepy creatures that lurk there in the night. With witches, monsters, ghosts, and goblins, the trail comes alive with Halloween's scariest creatures. Live music, food, and beer and wine are available from Shrewd Fox.  READ MORE

Children's Day - Dark Forest at Burn Brae Mansion

Glen Spey
Sunday, October 22, 2023
For one afternoon only, the Dark Forest is transformed to ditch the frights and focus on the delights of Halloween. It's the same Dark Forest walking trail, but done in the light of day with fanciful characters and fun especially for kiddos. There will be games, treat bags, and food and drink for sale. READ MORE

Wurtsboro Halloweenfest

Wurtsboro–FREE
Saturday, October 28, 2023
Join the kids' Halloweenfest in Veterans Park, featuring a kids' costume parade and contest, a pet costume parade and contest, and free crafts, candy, and games.    READ MORE

Places featured in this article:

The Sugar Loaf Performing Arts Center
Headless Horseman Hayrides and Haunted Houses
Headless Horseman Hayrides and Haunted Attractions
Kevin McCurdy's Haunted Mansion
Hudson Valley's Best After-School & Summer Camp
Downtown Nyack
Bethel Woods Center for the Arts