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Halloween Events in Chappaqua - Pleasantville - Mt. Kisco & Beyond

By Lisa Dunleavy October 8, 2019

Halloween is almost here and in Westchester County (and beyond) there are many fun (and scary) Halloween events to check out. Just click on the links below (in pink). 

Events for the whole family including younger children include:

Boo at the Zoo (Bronx Zoo). Annual Boo At The Zoo event at the Bronx Zoo runs on weekends in October. 

Brick or Treat at Legoland Discovery Center (through October 27)

Spooky Pumpkin Garden @ NY Botanical Garden (Daily except Mondays through 10/31)

Spooky Pumpkin Nights @ NY Botanical Garden (October 18, 19, 25, 26). Special night time event.

Sunnyside: Home of the "Legend" in Sleepy Hollow. During October, Sunnyside celebrates its connection to Washington Irving's classic tale, "The Legend of Sleepy Hollow." This daytime event is perfect for young kids and fun for the whole family. As you tour both floors of Irving's fascinating home, you will hear stories about what inspired Irving to write his most famous short story and see works of art inspired by The Legend of Sleepy Hollow. 

The Great Jack O'Lantern Blaze in Croton-on-Hudson. The tri-state area's biggest, most electrifying fall event returns with more pumpkin power than ever before! Meander through an historic, 18th century riverside landscape and discover a breathtaking display - all made of jack o' lanterns! Many dates are already sold out but tickets are available for select nights. 

Night of 1000 Jack O'Lanterns in Yorktown.

Halloween Train Show at Lasdon Park in Somers. (10/19, 20, 26 & 27)

Stew Leonard's Trick or Treat (10/23)

Town of Mt. Pleasant Ragamuffin Parade (10/25)

Ragamuffin Parade in Pleasantville (10/26)

Steffi Nossen Halloween Bash (10/26)

Boo at the Zoo at Bear Mountain (10/26)

A Halloween Haunt in Armonk (10/26 & 10/27). North Castle Historical Society event.

All Treats, No Tricks @ The Westchester (10/26). Celebrate Halloween with Disney Junior's Vampirina.

Halloween Carnival @ Mt. Kisco Library (10/26)

Tarrytown Halloween Parade (10/26)

Halloweekend @ Hudson River Museum (10/26 & 27)

Nyack Halloween Parade (10/26). 32nd Annual Event!

Ragamuffin Parade in Chappaqua -- this event has been cancelled and will not happen this year.

Boo Walk at Muscoot Farm (10/27)

Trick or Treat on the Farm in Stamford (10/27)

Halloween Horror at the Chappaqua Library (10/28). Grades K & up.

Trunk or Treat in Armonk (10/29)

Halloween Fun at the Chappaqua Library (10/30). Ages 4-6.

Spooky Tales @ Caramoor in Katonah (10/30). For children ages 3-8.

A Creepy, Crawly Halloween @ Westchester Children's Museum (10/31)

Downtown Chappaqua Halloween (10/31). New Castle residents can trick-or-treat during the day at local businesses.

Halloween on the Farm @ Muscoot (10/31)

Halloween on Main Street in Ossining (10/31). Trunk-or-Treat, DJ, and kids activities.


For Older Children and adults, check out these events:

Jay Ghoul's House of Curiosities at Lyndhurst (ages 7+). 40 minute nighttime performance at Lyndhurst. Select dates from October 17 - 31.

Sleepy Hollow Cemetery. There are multiple events at the eternal resting place of Washington Irving including their classic Daytime Tour and Evening Tour (Daytime Tour is better for young children). Events include "Beyond the Legendon 10/17 & 10/24 and  "Spooky Stories" on Sunday, October 20 & 27. Most events take place in the historic Washington Irving Memorial Chapel at the North Gate, 540 N. Broadway. These events do sell out so buy tickets online in advance. For more information, visit their website at sleepyhollowcemetery.org.

Sleepy Hollow Haunted Hay Ride. The Haunted Hayride has been a long-standing tradition in the Village of Sleepy Hollow and has frightened many innocents over the last 10 years. The Haunted Hayride will be held on Friday, October 25th. This event does sell out -- purchase tickets online at the event website.

Irving's 'Legend' in Sleepy Hollow. Master storyteller Jonathan Kruk offers a dramatic performance of Washington Irving's classic tale, The Legend of Sleepy Hollow. Featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel and flavored with live spooky organ music by Jim Keyes, Kruk's spellbinding storytelling captivates all audiences. Performances last about 45 minutes. Horseman's Hollow takes place at Philipsburg Manor in Sleepy Hollow. 

Horseman's Hollow at Philipsburg Manor. Taking the tale of The Legend of Sleepy Hollow to its darkest extremes, Horseman's Hollow returns to the village for 15 evenings of highly entertaining haunted mayhem. Philipsburg Manor transforms into a terrifying landscape. This event is recommended for children 10+. 

The Unsilent Picture at Philipsburg Manor. Settle in to an eerie evening performance featuring an original silent film starring Bill Irwin accompanied by live musicians and an in-the-flesh special effects Foley artist. Ages 10+.

Forest O' Fears: The Haunting of Cedar Lane in Ossining. For older kids (ages 13+) -- go the weekend of October 18-19. A Family Friendly event will be held on October 25-26.

The Haunt at Rocky Ledge in North White Plains. The Haunt at Rocky Ledge is a frightening attraction that combines the outside element with the indoors! This event features two haunted houses, a long terrifying walk through the woods, and the only haunted cornfield in Westchester! Recommended for ages 10+. Visit the event website for more information.

Scared By The Sound in Rye. Rye Playland gets transformed into a Halloween haunted house on weekends in October. See a haunted wine cellar, creepy morgue and tunnels of doom. Recommended for children 10+. For more information, visit the event website.

Happy Halloween!