Weekend Fun for Westchester Families: Halloween, Applefest, Children’s Book Festival, Oct. 3-4

9/30/15 - By Susan Miele

With October comes the beginning of the Halloween season, and all the associated festivals, spectacles, parades and haunted houses throughout Westchester and the Hudson Valley. We’ve populated our Event Calendar with a ton of these festivities (as well as a variety of non-Halloween events for when you crave diversity), so take a peek and plan ahead. Stay tuned, because much more is coming!

The Rivertowns, strongly associated with Washington Irving’s “The Legend of Sleepy Hollow,” go all out for Halloween, with month-long events that start this weekend like The Great Jack O Lantern Blaze (which is already sold out for this weekend) and The Legend Behind the 'Legend', as well as haunted happenings for older kids like Scared by the Sound.

For some non-Halloween happenings, catch Warwick Applefest, the Chappaqua Children’s Book Festival or the Annual Horse Show and Country Fair, to name a few. Also consult our guide for scenic autumn drives to savor the splendor of the season.

Read on for our top weekend picks, but be sure to also check our Event Calendar and October GoList for more family fun this weekend and beyond!

OUR LATEST VIDEOS

All Weekend

The Legend Behind The 'Legend' - Irvington
Visitors can enjoy a shadow puppet performance of “The Legend of Sleepy Hollow” and experience one of Washington Irving’s spooky tales on a walk through the woods.

Horseman’s Hollow - Sleepy Hollow
Prepare to be scared stiff at Philipsburg Manor, which transforms into a house of horror ruled by the undead, the evil and the insane in October.

Lasdon Park Halloween Train Show - Somers 
This annual holiday train show takes on a dinosaur theme this year and includes a dinosaur topiary, wagon rides, a hay maze and more.

Peekskill Rotary Annual Horse Show and Country Fair - Peekskill
In addition to English and Western riding contests throughout the day, families can enjoy pony and hay rides, bouncy houses, a pet parade, demonstrations of kung fu and boxing, a magician, a food tent and more. Free admission

Saturday, October 3

Family Saturdays @ the Lab - Pleasantville
Drop in to learn how to make your own claymation stop-motion film at this FREE program.

Chappaqua Children’s Book Festival - Chappaqua
Meet more than 85 authors, hound them for autographs and hear some excerpts at this annual event that celebrates children’s literature. Bring your whole family for food, kid-friendly activities, entertainment of course, books! FREE

Scared By The Sound - Rye
Older kids can savor the fear factor of the Crypt Walk, Haunted Wine Cellar, Creepy Morgue and Tunnels of Doom.

See all Saturday events.

Sunday, October 4

Warwick Applefest - Warwick
The Warwick Applefest is expected to attract over 35,000 visitors, with its children’s carnival, farmer’s market, music, food, craft vendors and entertainment on several stages. Apple pie contest for kids 16 and under. Admission is free.

Scarsdale Concours d'Elegance - Scarsdale
Car enthusiasts can delight in viewing more than 125 classic vehicles while supporting local charities. 

See all Sunday events.

Beyond Westchester

For more Halloween-themed fun, the Bronx Zoo's annual Boo at the Zoo kicks off this weekend, with hay mazes, musical theater, magic, 3D carved pumpkins, the Extinct Animal Graveyard, Jack O ‘Lantern Illumination and more.

For a cool theatrical concept, try Story Pirates at Symphony Space, where improvisational actors bring to life the imagination of children, who write the stories. Hardly formulaic, these plot twists can include hot dogs saving the world, and characters such as Captain Waffles and Moneyhead Alan. 

Don't forget—there are more ideas for fun family outings in our Events Calendar.

Photo credit: Chappaqua Children's Book Festival / Jamie Kilgore Photography