The pie eating contest is just the start of the fun at the Armonk Cider and Donut Festival. Photo courtesy of the festival
Best Harvest Festivals & Pumpkin Festivals in Westchester and the Hudson Valley for Fall Fun in 2025
Book your tickets now if you want to see the annual spectacle that is The Great Jack O'Lantern Blaze at Van Cortlandt Manor. Photo by the author
21 Best Things To Do in Westchester and the Hudson Valley with Kids September 2025, According to Mommy Poppins Editors
Outhouse Orchards Corn Maze. Photo by Matt Nighswander
GUIDE
Westchester & Hudson Valley Kids Fall Guide: Best Things to Do in 2025
Pick from a number of apple varieties at Hudson Valley orchards. Photo by Leslie Seaton via Flickr
Apple Picking in the Hudson Valley: Best Apple Farms and Apple Festivals
Apple picking is one of the family-friendly fall activities you can enjoy in the Hudson Valley with Kids. Photo courtesy of the author
Your 2-Day Itinerary for a Kid-Approved Fall Weekend in the Hudson Valley
Woodstock is the perfect fall getaway and just a two-hour drive away. Photo by Diana Kim
30 Fall Day Trips from NYC for Families
Get ready for back to school with all the right supplies, classes, and tips.
GUIDE
Back-to-School Guide 2025-2026
Enjoy glorious views on the Walkway Over the Hudson. Photo by Fred Schaeffer/courtesy of the Walkway.
50 Best Things To Do in the Hudson Valley with Kids
A visit to the United States Military Academy is a lesson in history and patriotism, but also tons of fun for families.
Visiting West Point with Kids: 37 Top Things To Do near the United States Military Academy
Kids can run, swing, slide, and even make music at Sally’s Dream Playground in Montgomery. Photo by Katherine Dhurandhar
Top Playgrounds in Westchester and the Hudson Valley Worth Driving To
The Saugerties Lighthouse is a stunning getaway no matter the season.
Sleep in a Lighthouse and More Hudson Valley Family Resorts and Hotels
Summer camps are a great way to make new friends and develop new skills
GUIDE
Summer Camps Guide for Westchester & Hudson Valley Kids
The Play Place in Elmsford is one of Westchester's top indoor play spaces.
Top Indoor Playgrounds and Play Spaces in Westchester
Roam the the cedar walk and gardens at Caramoor for a free, fun outing. Photo by Gabe Palacio
41 Free Things To Do in Westchester with Kids
Enjoy water sports at Westchester Summer Day in Mamaroneck. Photo courtesy of the camp
Best Summer Camps in Westchester for Kids
Palisade Center's Climbzone features themed rock walls as high as 40 feet. Photo courtesy of Climbzone.
20 Best Things To Do at the Palisades Center Mall with Kids
The Ausable Chasm has been described as the Grand Canyon of the Adirondacks and it's one of our top 100 things to do in New York State with kids. Photo by Anna Fader
Ultimate New York Bucket List: 100 Things To Do with Kids in NY State
Poughkeepsie's Gravity Vault is an indoor rock-climbing gym with classes for kids as young as 5. Photo by Kaylynn Ebner
Best Kids' Indoor Playgrounds and Play Spaces in the Hudson Valley
Mount Kisco's Grand Prix New York, a go-kart hot spot, offers birthday parties with racing, arcade play, and virtual reality.
17 Best Indoor Party Places for Kids in Westchester
GUIDE
Guide to Indoor Fun for Westchester & Hudson Valley Kids
Kids explore the great outdoors Hudson Highlands Nature Center. Photo courtesy of the center
School Break Camps in Westchester and the Hudson Valley: Winter and Spring Break Camps
At Moe's Southwestern Grill, kids eat free on Tuesdays with the purchase of an adult entree. Photo courtesy of the restaurant
Restaurants Where Kids Eat Free in Westchester and the Hudson Valley
Kids under 1 are FREE hours at the Westchester Children’s Museum. Photo courtesy of the museum
GUIDE
Guide to Free Fun Things to Do with Westchester Kids
Kids can peek into the marine life in the aquariums at the Marine Education Center in Mamaroneck. Photo by Susan Miele
19 Free Things To Do Indoors in Westchester and the Hudson Valley: Indoor Places to Play
Castle Fun Center in Chester has a giant inflatable park, a rock wall, laser tag, and more. Photo by Katherine Dhurandhar
15 Family Fun Centers in Westchester and the Hudson Valley
Grab a colorful treat at Harley's Sweet Shop in Woodstock. Photo courtesy of the shop
25 Best Things To Do in Woodstock, NY, with Kids
Kids can climb the walls at the Cliffs in Valhalla. Photo courtesy of the Cliffs
32 Things To Do on a Rainy Day Indoors in Westchester and the Hudson Valley
Touch the soft rabbits at the Greenburgh Nature Center's petting zoo in Scarsdale. Photo courtesy of the center
Best Animal Petting Zoos near Westchester and the Hudson Valley Where Kids Can Meet Animals
Peekskill, NY, is a lovely riverfront community that acts an the unofficial gateway to the Hudson Valley.
25 Best Things To Do in Peekskill, NY, with Kids
Explore what makes things fly with the Westchester Children's Museum's Wind Tunnel Design Challenge. Photo courtesy of the museum
Visiting the Westchester Children's Museum in Rye: New and Ongoing Exhibits
Romp through the woods in the beautiful Catskills. Photo by Deborah Dadlani
40 Best Things To Do in the Catskills with Kids
GUIDE
Classes Guide for Westchester & Hudson Valley Kids
Tig & Peach offers drop-in, no reservations required, open play 7 days a week.
7 Indoor Playgrounds in Westchester and the Hudson Valley for a Wild Romp
Friends young and old enjoy the attractions and Legoland New York, the first major theme park in the Northeast in 40 years.
  VIDEO
Legoland New York: A Guide to Visiting the Hudson Valley Theme Park with Kids
Frost Valley YMCA offers a variety of day and overnight camps for kids ages 5-14. Photo courtesy Frost Valley YMCA
Affordable Summer Camps in Westchester and the Hudson Valley
These boredom-busting activities turn a stuck-at-home day into a lasting memory.
75 Indoor Activities for Kids on a Rainy Day
Kids love a birthday party filled with games and pizza at Chuck E. Cheese. Photo courtesy of Chuck E. Cheese
Best Fun Restaurants for Kids' Birthdays in Westchester
Head to the Mid-Hudson Discovery Museum from 5-8 pm on the third Saturday of the month to explore the museum for free, Photo by the author
Free Museums and Museum Days in Westchester and the Hudson Valley
Creating a baking soda volcano is a classic science experiment for kids. Photo by Sara Marentette Nighswander
67 Easy Science Experiments for Kids To Do at Home
Kids can while away hours of a day with a set of watercolors and a stack of new paper for painting. Photo by Sara Marentette
Crafts for Kids: 100 Awesome Art Projects
These kids' movies are classic hits!
75 Best Movies for Kids: Top Family Movie Night Ideas
GUIDE
Guide to Playgrounds & Parks in Westchester & the Hudson Valley
Suncatcher_Liz Baill @creativishmom
GUIDE
Crafts for Kids Guide: Thousands of Craft Ideas
Enjoy author meet-and-greets plus a family-fun zone and hand-on activities at the Chappaqua Children's Book Festival this Saturday. Photo courtesy of the event
Top Things To Do This Weekend in Westchester and the Hudson Valley with Kids

Best Halloween Events in Westchester and the Hudson Valley 2025 for Kids and Families

The Great Jack-o'-Lantern Blaze in Van Cortlandt Manor is a must-do Halloween event in the tri-state area. Photo courtesy of the Historic Hudson Valley
The Great Jack-o'-Lantern Blaze in Van Cortlandt Manor is a must-do Halloween event in the tri-state area. Photo courtesy of the Historic Hudson Valley
9/21/25 - By Katherine Dhurandhar

Spooky season is here, and there’s no shortage of great Halloween events in Westchester and the Hudson Valley. 

Sleepy Hollow and Tarrytown are prime Halloween destinations due 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, like haunted houses, which often have not-so-scary days for younger kids. Little ones can also 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 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, and turn to our Halloween Fun Guide to get the most out of this fun season. 

Sign up for our newsletters to get stories like this delivered directly to your inbox.

OUR LATEST VIDEOS

Best Halloween Events in Westchester 2025

The Great Jack-o'-Lantern Blaze at Van Cortlandt Manor

Croton-on-Hudson
Multiple dates through November 16, 2025
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. New for 2025 is a jack-o'-lantern big top adventure, a Wicked-themed, emerald-hued storybook pumpkin dreamscape, and the Headless Horseman’s Hideaway featuring spooky sips and haunting visits from the Horseman himself.  READ MORE

Mystic Moon

North Salem
Multiple dates from September 19 through November 6, 2025
Unlike traditional Halloween attractions, Mystic Moon at Harvest Moon Farm & Orchard trades fright for wonder, inviting guests into a world of moonlit magic. This 40-minute adventure is crafted for both children and adults, weaving together an atmosphere that’s equally mystical and enchanting. READ MORE

Legendary Tours of Washington Irving's Sunnyside

Irvington
Select dates through November 9, 2025
A Halloween tradition returns, offering daytime holiday fun for all ages. Tour the author's home and enjoy the grounds during this special "Legend of Sleepy Hollow"-themed tour of the estate. READ MORE

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

Sleepy Hollow
Fridays through Sundays, October 3 - November 1, plus October 13, 2025
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-Saturdays in September and daily in October and November 2025
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

Sleepy Hollow's Twilight Village at Philipsburg Manor

Sleepy Hollow
Fridays-Sundays, October 3 - November 1, plus October 13, 2025
Looking for the true heart of Sleepy Hollow? You’ll find it at Twilight Village at Sleepy Hollow's historic Philipsburg Manor. Discover delightful and mysterious creatures who will tell your fortune, croon creepy tunes, and tell tall-ish tales of legends and lore. Shop for super Sleepy Hollow swag at the Halloween night market and enjoy cocktails, mocktails, and tasty snacks. Watch where you’re going, or you could come face-to-no-face with the Headless Horseman himself! READ MORE

The Haunt at Wildcliff Mansion

New Rochelle
Fridays-Sundays from Friday, October 10 to Sunday, November 2, 2025
Set on a windswept cliff overlooking Echo Bay in New Rochelle, this immersive Halloween experience will transport attendees to the haunted estate of Dr. Wildcliff, a reclusive botanist with a dark obsession. Guests will explore Dr. Wildcliff’s forgotten laboratory, the restless cathedral and graveyard, the haunted corn maze, and the labyrinthine halls of Wildcliff Mansion, encountering ghostly figures and reanimated horrors at every turn. READ MORE

Sleepy Hollow Paddleboarding Witches Festival

Sleepy Hollow–FREE
Sunday, October 12, 2025
The Paddleboarding Witches Festival features a costumed paddleboarding session followed by a party with food trucks, vendors, and a live telling of the Legend of Sleepy Hollow.  READ MORE

Sleepy Hollow Haunted Hayride

Sleepy Hollow
Friday & Saturday, October 17-18, 2025
The Village of Sleepy Hollow’s annual Haunted Hayride returns for two nights of frights, "making hay" of the setting of Washington Irving's "The Headless Horseman." Before or after, head to the free block party on Beekman Avenue that features music, children's activities, and vendors. READ MORE

Halloween Weekend at the Westchester Children's Museum

Rye–FREE with museum admission
Saturday, October 18-Sunday, October 19, 2025
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.  READ MORE

Village of Mamaroneck Spooktacular Sunday

Mamaroneck
Sunday, October 19, 2025
The Village of Mamaroneck and Mamaroneck Chamber of Commerce invite you to grab your trick-or-treat bag, dress up as your favorite character, and join the Annual Spooktacular Halloween parade and festivities. READ MORE

Tarrytown Halloween Parade

Tarrytown–FREE
Saturday, October 25, 2025
This spooky spectacle of marchers and floats is back with costume and float-decorating contests. The parade begins in Patriot Park and ends at Main Street with a block party.  READ MORE

Cross County Center Halloween Spooktacular

Yonkers–FREE
Saturday, October 25, 2025
Kids can enjoy trick-or-treating, inflatables, a performance and meet & greet with the Wicked witches, and more at Cross County Center. READ MORE

Best Halloween Haunted Houses and Trunk-or-Treats in Orange County 2025

Pure Terror Scream Park

Monroe
Fridays-Sundays, September 19-November 2, 2025, plus October 30
An extensive Halloween attraction, Pure Terror features 10 haunted houses, including the 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.  READ MORE

Boo Arrow Farm Haunted Hayride

Pine Island
Multiple dates from October 1-25, 2025
Blue Arrow Farm celebrates Halloween with a pair of fun and frightful attractions. Families with wee ones should attend early in the evening for a not-so-spooky family train ride. After dark, the Boo Arrow Farm turns into a frightfully haunted hayride. Stick around for live music, vendors, face painting, and other fun. READ MORE

Legoland's Brick-or-Treat Presents Monster Party

Goshen
Fridays-Sundays, October 2- November 2, 2025, plus October 13
The Monster Party begins the moment you step into the park with a boo-tifully decorated entry arch. Meet Lego Monster characters like Spider Lady and Wacky Witch and make your way to the treat stations around the park. Don’t forget your costumes! READ MORE

"I Spy" Halloween Nature Trail at the Hudson Highlands Nature Museum

Cornwall
Saturday, October 25, 2025
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

Top Halloween Festivals and Haunted Houses in Ulster County 2025

Headless Horseman Haunted Houses

Ulster Park
Fridays through Sundays, October 3 - November 1, 2025, plus Saturdays, September 20 and 27
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 4 & 18, 2025
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

Catskill Mountain Railroad's Pumpkin Express

Kingston
Weekends, October 18-26, 2025
Take a spectacular journey along the former Ulster & Delaware Railroad corridor and see the natural beauty of the Catskills from the Catskill Mountain Railroad’s unique perspective aboard Ulster County’s only scenic train. Pumpkin Express trains travel the tracks to the Pumpkin Patch where passengers will be able to select their favorite pumpkin to take home and decorate. READ MORE

MyKingstonKids Halloween Fest & Parade

Kingston–FREE
Saturday & Sunday, October 25-26, 2025
The MyKingstonKids Halloween Fest is now a two-day event with a parade and festival that includes vendors, food, trick-or-treating, carnival games, a costume contest, and more. READ MORE

Best Halloween Events and Trunk-or-Treats in Dutchess County 2025

Kevin McCurdy's Haunted Mansion

Wappingers Falls
Fridays-Sundays, October 3-November 1, also September 27, 2025
KM’s Haunted Mansion celebrates its 49th anniversary with The Keeper—a haunting experience where every story has an ending...what will yours be? Step into a realm of intricate haunt mazes, bigger scares, and creative twists around every corner. Encounter exclusive interactive performances and dive into a trail of terror filled with surprises at every turn. READ MORE

A Very Fluffy Halloween at Lilymoore Farm

Pleasant Valley
Weekends, October 11-26, 2025
It’s a Halloween fest – only way cuter. Meet fluffy alpacas and llamas strutting their stuff in lion’s manes, rainbows, or even as a butterfly. It’s the perfect blend of cuteness and hilarity—who wouldn’t want a selfie with an alpaca dressed as a hippie? READ MORE

Kids' Day at Kevin McCurdy's Haunted Mansion

Wappingers Falls
Monday, October 13, 2025
This is a special show for younger kids that won't give them nightmares. Kids' day entertainment includes magic shows and activities like trick-or-treating with friendly monsters. READ MORE

Wicked Wappingers Trunk or Treat & Halloween Parade

Wappingers Falls
Saturday, October 18, 2025
Wicked Wappingers is a day of spooky celebration at the Village of Wappingers Falls. The parade kicks off at noon, followed by festivities at Mesier Park, where there will be a trunk or treat, music, food, vendors, and games. READ MORE

Best Halloween and Trick-or-Treat Events in Rockland County 2025

Halloween Carnival - Nanuet Town Centre

Nanuet–FREE
Saturday, October 18, 2025
Celebrate Halloween carnival-style at Nanuet Town Centre with interactive games, stilt walkers, pumpkin crafts, skeleton encounters, spooky photo ops, and delicious festive treats! READ MORE

Boo at the Bear Mountain Zoo

Bear Mountain
Saturday, October 25, 2025
Head to Bear Mountain Trailside Museums and Zoo for a spooky good time. Arrive between 10:30 to 11am to make bear treats, then watch the bears explore their den full of Halloween-themed enrichment. Learn about vultures, owls, bears, and other animals. Family friendly activities include pumpkin decorating, matching games, and crafts. Wear your favorite not-so-spooky Halloween costume!  READ MORE

Nyack Halloween Parade

Nyack–FREE
Saturday, October 25, 2025
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

Awesome Halloween Festivals and Events in Sullivan County 2025

Peace, Love & Pumpkins at Bethel Woods Center for the Arts

Bethel
Wednesdays - Fridays from October 10-November 2, 2025
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 11-25, 2025
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

Wurtsboro Halloweenfest

Wurtsboro–FREE
Saturday, October 25, 2025
Join the kids' Halloweenfest in Veterans Park, featuring a kids' costume parade and contest, a pet costume parade and contest, cookie decorating, a live wood-carving demonstration, a bake sale, and free crafts, candy, and games.  READ MORE

Places featured in this article:

Headless Horseman Hayrides and Haunted Houses
Headless Horseman Hayrides and Haunted Attractions
Kevin McCurdy's Haunted Mansion
Kevin McCurdy's Haunted Mansion
Downtown Nyack
Bethel Woods Center for the Arts

About the Author

Katherine Dhurandhar
Katherine Dhurandhar is a Community Publisher for Mommy Poppins, representing the Westchester and Hudson Valley region of New York, and a freelance copyeditor for Westchester Publishing Company. In her free time, she enjoys hiking, camping, and traveling with her husband and son.
Recent Articles By Katherine Dhurandhar:
Read more articles by Katherine Dhurandhar.