When October rolls around, Westchester becomes a playground for spooky fun, community events, and seasonal magic. Whether you're a local or considering moving to the area, here are 10 Halloween hotspots in Westchester you should check out this year:
1. The Great Jack O’Lantern Blaze (Croton-on-Hudson)
Meander through more than 7,000 hand-carved, illuminated pumpkins at Van Cortlandt Manor. It’s a stunning, immersive experience complete with themed displays, special effects, and seasonal treats.
2. Sleepy Hollow Cemetery Tours (Sleepy Hollow)
Take a lantern-lit or daytime walking tour through the historic Sleepy Hollow Cemetery. Learn about Washington Irving, the cemetery’s history, and the legends that make this place iconic.
3. Irving’s ‘Legend’ at Old Dutch Church (Sleepy Hollow)
Catch a dramatic retelling of The Legend of Sleepy Hollow at the historic Old Dutch Church. It’s a perfect mix of theater, local lore, and spooky storytelling.
4. Scared by the Sound Haunted House at Rye Playland
Face your fears as you step into over 12,000 square feet of nightmares, featuring horrifying favorites like the Crypt Walk, Creepy Morgue, Haunted Wine Cellar, and Tunnels of Doom — all more intense and immersive than ever. With terrifying new scenes and returning fan favorites, the monsters along the waterfront are waiting for you.
5. Lyndhurst After Dark (Tarrytown)
This experience through the Mansion explores the slightly darker side of history through the stories of those who lived at Lyndhurst. Visitors will have the opportunity to experience the architecture, decor, and collection items on display while listening to performers share stories about the traditions of the past. Please note that this is not a haunted house!
6. The Headless Horseman Files / Spirits of Sleepy Hollow Country
Part of Sleepy Hollow’s broader Halloween offerings. Haunted tours, ghost stories, and immersive experiences across Sleepy Hollow Country.
7. LEGOLAND’s Brick-or-Treat.
For the kids, there’s nothing like a day full of spooktacular activities at Legoland. They can choose from a scavenger hunt, the chance to create their own magical potion, meet-and-greets with characters, and more.
8. Paint a Headless Horseman Pumpkin & Special Events (Sleepy Hollow Cemetery)
On select days, you can join artist Heather Gleason to paint your own pumpkin with a Headless Horseman theme. Other interactive events include murder mystery nights and theatrical readings.
9. Local Pumpkin Patches & Farms
Throughout Westchester you’ll find pumpkin patches, corn mazes, cider donuts, and farm stands. Perfect daytime outings for families looking to embrace all things autumn.
10. Harvest Moon Farm & Orchard (North Salem)
Pumpkin picking, a corn maze, hayrides, live music, and fresh cider donuts. This farm is a fall favorite and brings Halloween vibes without the scares.
Halloween fun in Westchester isn’t just about pumpkins and costumes—it’s also a peek into what community life is really like. Seasonal events tell you a lot about a neighborhood:
Community spirit – People out in the streets, parks, and local spots enjoying time together.
Convenience – Walkable access to parades, festivals, and family activities.
Charm – Historic sites, cozy downtowns, and traditions that give each town its own personality.
So if you’re exploring homes this fall, keep an eye on the calendar. These events highlight neighborhoods that aren’t just great places to visit—but wonderful places to live.
