Autumn in Westchester is a magical time — crisp air, blazing foliage, and an undercurrent of spectral mischief. As Halloween approaches, this region transforms into a playground for the spooky and the sublime. Whether you’re looking for a family-friendly outing, a hair-raising experience, or a walk through literary legend, here are seven must-do Halloween activities in and around Westchester.
1. Wander through the Great Jack O’Lantern Blaze
One of the crown jewels of the Hudson Valley Halloween season, the Great Jack O’Lantern Blaze never disappoints. Over 7,000 hand-carved pumpkins, synchronized lighting, themed displays, and hauntingly beautiful walkways make this immersive show something you'd be remiss to skip. Historic Hudson Valley+2Historic Hudson Valley+2
New for 2025: expect a jack-o’-lantern big top, a “storybook pumpkin dreamscape,” and special hideouts where the Headless Horseman may make an appearance. Historic Hudson Valley
Tip: Book tickets in advance and plan for weekend crowds.
2. Immerse yourself in Sleepy Hollow Country’s Halloween lore
Sleepy Hollow, famously tied to Washington Irving’s The Legend of Sleepy Hollow, leans fully into its ghostly reputation. During October you can:
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Join Twilight Village at Philipsburg Manor, with fire performers, markets, and eerie storytelling. Historic Hudson Valley
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Explore The Headless Horseman Files, an immersive detective-style experience set in Sleepy Hollow. Historic Hudson Valley
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Attend Irving’s “Legend”, a dramatic storytelling production weaving in characters of the region’s haunted past. Historic Hudson Valley
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Take a lantern walk or ghost tour by night, feeling the chill in the old graveyards. Visit Sleepy Hollow+2Historic Hudson Valley+2
These are more atmospheric than “haunted house fright,” making them ideal for all ages.
3. Step behind the veil at the Ghost Tour of Tarrytown Music Hall
For lovers of theater — and of the unexplained — the Ghost Tour of Tarrytown Music Hall is a compelling choice. Guided by master storyteller Jonathan Kruk, you’ll explore tales of paranormal encounters, backstage secrets, and historic lore within this old theater. Westchester Magazine
The tour runs on select dates from September through early November. Westchester Magazine
4. Visit Lyndhurst Mansion’s Halloween Opening Party
Set along the Hudson River in Tarrytown, Lyndhurst Mansion offers a stately but spirited Halloween kickoff each year. Their “Halloween Opening Season Party” includes spooky tours, seasonal decorations, and a festive atmosphere. Lyndhurst Mansion
It’s a refined way to dip your toes into the Halloween season — elegant, moody, and full of architectural and historical charm.
5. Enjoy family-friendly fall & Halloween festivals
If you’re out with children (or just love a lighthearted celebration), Westchester delivers plenty of approachable Halloween fun:
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Spooktoberfest in Hartsdale: inflatables, crafts, games, and seasonal treats. Westchester Family
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Playland “Howl-O-Ween” Pet Parade (Rye): bring your costumed pup and enjoy a pet-centered parade on the boardwalk. Westchester Family
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Farming & Witchcraft at Hilltop Hanover Farm in Yorktown Heights: learn about folk remedies and herbal lore in a hands-on workshop. Westchester Family
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Nightmare on Bank Street (Jefferson Valley): haunted trail, maze, games and costume contests. Westchester Family
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Halloween Weekend at the Westchester Children’s Museum: skeleton studies, science demos, costumed fun. Westchester Children's Museum
These events give you that autumnal Halloween buzz without going full-shock.
6. Tour Sunnyside — home of Washington Irving
For literary and historic buffs, Legendary Tours of Sunnyside (Irving’s home in Irvington) offers Halloween-themed guided visits. The house and grounds are imbued with Irving’s spirit and provide a quieter but resonant connection to the region’s classic ghost lore. Mommy Poppins
This is a great daytime option — combine it with a lunch or stroll along the Hudson River afterward.
7. Brave a haunted house or spooky attraction
If you’re in the mood for some genuine fright, Westchester has several haunted houses, hayrides, and spook walks listed on regional calendars. Westchester Haunted Houses+2Westchester Haunted Houses+2
One recurring local mention is Nightmare Circus, a haunt run out of Sycamore Park (check local listings for dates/times). Reddit
Also, WestchesterHauntedHouses.com maintains an up-to-date calendar of all the region’s scarier offerings. Westchester Haunted Houses+1
🎃 Tips for a Spooktacular Halloween in Westchester
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Check dates in advance. Many events run only on weekends or specific nights, and tickets often sell out.
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Mix in daytime and nighttime activities. Use the daylight hours for farms, walks, and tours; save the after-dark moments for ghost tours and haunted houses.
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Dress in layers. October nights can be chilly.
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Plan for travel time. Westchester traffic, especially near the Hudson River towns, can get heavy in the fall.
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Don’t overdo it. Halloween is best savored slowly. Try to pick 2–3 top events and leave breathing room in your schedule.
Westchester in October is a rare combination: woodsy, historic, and spooky fun all at once. Whether you want to be thrilled or simply charmed by jack-o’-lanterns and ghost stories, there’s something here for every Halloween appetite. Let me know if you want this year’s dates or maps for any of these spots — I’d be happy to help plan your haunted itinerary.