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Why You Should Spend Halloween in Westchester County, New York

by Holly Riddle

Oct 7, 2025

Lyndhurst © James Kirkikis | Dreamstime.com

Destinations / North America

Just a short distance from New York City, Westchester County, New York, offers plenty to keep you occupied this month, from classic spooks in Sleepy Hollow to ample opportunities for leaf-peeping. Here’s how to spend a Halloween getaway to this bucolic locale.

 

  • Walk through a jaw-dropping display of more than 7,000 carved pumpkins at The Great Jack O’Lantern Blaze. Held at Van Cortlandt Manor in Croton-on-Hudson, this event goes nightly through Nov. 16.
  • Visit Lyndhurst Mansion for a seasonally appropriate, candle-lit after-dark tour, running Oct. 16–26. If you’re only in town over Oct. 25–26, make sure to also check out the mansion’s Gothic Harvest Market, for all your witchy wares.
  • Head to Washington Irving’s Sunnyside to take in a retelling of The Legend of Sleepy Hollow. Performances take place through Nov. 1, Friday–Sunday, multiple times per day.

 

Prefer to spend a fall vacay taking in the leaves rather than celebrating all things All Hallows’ Eve? Hop aboard a fall foliage helicopter tour, or strap on your hiking boots and head to one of the county’s many hiking hot spots. The Ward Pound Ridge Reservation offers 35 miles of trekking over 4,000 acres.

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