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

Where to Trick-or-Treat in Southern Westchester Halloween 2023

Rye

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.

Yonkers

The Cross County Shopping Center is hosting FREE Halloween events as part of its Halloween Spooktacular on Saturday, October 21, 2023. In addition to trick-or-treating, there will be arts and crafts, dancing, and more. 

White Plains

The city’s Highlands neighborhood goes all out on Tuesday, October 31, 2023. 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.

Sleepy Hollow 

Arguably the top spot to celebrate Halloween in Westchester—the parade, the events, the history!—it's no wonder Sleepy Hollow also has some great trick-or-treating. In particular, we hear the neighborhoods of Webber Park and Sleepy Hollow Manor are fun picks. 

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

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

Where to Trick-or-Treat in Northern Westchester this Halloween

Katonah

Head to Muscoot Farm on Saturday, October 21, 2023 for their Trick or Treating at the Farm, which runs from 12pm to 3pm—and is totally FREE. 

Pleasantville

On Halloween, visit 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. Also, since so many families are expected, non-residents can drop off candy to residents in the weeks leading up to Halloween to help them with the large haul they’ll need. Talk about getting in the spirit!

Armonk

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

Briarcliff Manor 

In-the-know visitors recommend the "tree streets" in Briarcliff Manor, located near Todd Elementary School, for some great trick-or-treating. As we're told, the homes are well-decorated, there are lots of young families—and there's plenty of police presence to help with traffic and parking. A win-win!  

Trick-or-treat early at the  Trunk or Treat and Halloween Parade at Mesier Park  Photo courtesy of Wappingers Falls PBA

Where to Go Trick-or-Treating in Dutchess County in 2023

Wappingers Falls

Get in some trick-or-treating early with the Trunk or Treat and Halloween Parade at Mesier Park on Saturday, October 22, 2023. Along with trick-or-treating, you’ll find a pumpkin patch, DJ, food, and more.

Best Places to Trick-or-Treat in Putnam County this Halloween

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.

This post was originally published in 2015 and has since been updated.