The Best Places to Trick-or-Treat in Westchester and the Hudson Valley

Don your best costume and enjoy trick-or-treating in Westchester. Photo by Meagan Newhart
Don your best costume and enjoy trick-or-treating in Westchester. Photo by Meagan Newhart
10/14/22 - By Lisa Johnston

When it comes time to hit the streets, we've found the best spots to trick-or-treat in Westchester and the Hudson Valley. These local neighborhoods are well-known for family-friendly Halloween fun and events where little goblins and ghouls can trick-or-treat to their hearts' content.

Whether you're looking for an alternative to your neighborhood or you want to add another stop to your trick-or-treating route, check out our picks below and be sure to bookmark our Westchester Kids Halloween Guide for all our top picks this spooky season, including the best Halloween events nearby and our favorite local haunted houses in Westchester and beyond. 

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Where To Go Trick-or-Treating in Southern Westchester


Zip Realty once crowned Rye as one of the best places for trick-or-treaters, based on walkability and the presence of single-family homes. It also took home prices into consideration, rationalizing that the biggest houses give out the best candy. We’re not sure if that last one holds water, but we do know Rye is also the source of other entertaining Halloween happenings. 24/7 Wall Street, meanwhile, named Rye the best town for trick-or-treating in New York a few years back, noting its strong kid-to-adult population ratio.


RELATED: Free, Family-Friendly Halloween Parades and Events for Westchester Kids

Trick or treat in Westchester Stew Leonards
Go trick-or-treating throughout Stew Leonard's on Halloween. Photo courtesy of Stew Leonard's


The Cross County Shopping Center is hosting FREE Halloween events as part of its Halloween Spooktacular on Saturday, October 22. In addition to trick-or-treating, there will be arts and crafts, dancing, and more. The following week, on Wednesday, October 26, Stew Leonard's hosts trick-or-treating throughout its store. While the event is FREE, you have to register for a timed-entry slot of time. 

White Plains

The city’s Highlands neighborhood goes all out on Monday, October 31. The close proximity of the houses and the easily walkable streets make it a great spot to visit—and scoop up plenty of candy while showing off those costumes.

RELATED: Halloween Drive-thrus in the Tri-State Area Pumpkins, Lights, and Haunted Scene

Trick or treat in Westchester Northern Westchester
Parades, a spooktacular, and Octoberfests are all on the Halloween schedule in Northern Westchester. Photo by Mommy Poppins

Where To Go Trick-or-Treating in Northern Westchester

Cross River

Enjoy a “spooky trick-or-treating trail” as part of the County’s Spooktacular Oktoberfest at the Trailside Nature Museum in Cross River. There will also be lots of other activities—from pumpkin decorating to stories to an outdoor beer garden for the adults.


On Halloween, head over to the well-decorated trio of streets in town–Edgewood Avenue, Grove Street, and Great Oak Lane–that have been dubbed “Halloween Streets.” As one local tells us, the roads are closed to traffic to make it easier for kids to trick-or-treat and since so many families are expected, leading up to Halloween, non-residents can drop off candy to residents to help them with the large haul they’ll need. Talk about getting in the spirit!


We hear that School Street is the spot for some great trick-or-treating in town, with its roads closed. And similar to Pleasantville, people in town help ease the treat-buying burden for local neighborhood residents by donating candy.

Where To Go Trick-or-Treating in Dutchess County

Wappingers Falls

Get in some trick-or-treating early with the Trunk or Treat and Halloween Parade at Mesier Park on Saturday, October 22. Along with trick-or-treating, you’ll find a pumpkin patch, DJ, food, and more.

Where To Go Trick-or-Treating in Putnam County

Cold Spring

The radio station 101.5 WPDH dubbed Parrott Street in Cold Spring “the best trick-or-treat spot in the Hudson Valley” a few years back. The neighborhood is known for its awesome decorating and throngs of costumed families.

Originally published in 2015.