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.
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Best Halloween Events in Westchester 2025
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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