Halloween in Ossining | InOssining.com

Halloween in Ossining

Celebrate Halloween in Ossining with these fun events that different organizations have put together for Ossining residents! From Haunted Hay Rides to a Halloween Pet Parade, here is everything you need to know about to celebrate Halloween in your town, in chronological order. And to see a calendar of all the events happening in Ossining in October and beyond, you can check out our Ossining Events Calendar.

1. Scary Little Stories Series

Ossining Forest O Fears

In this series of classes, participants will learn how to analyze stories to unpack layers of meaning. Stories include; “The Lottery” by Shirley Jackson, “Taste” by Roald Dahl, and “The Black Cat” by Edgar Allen Poe. Copies of each short story are available at the Information Desk. Stories cannot be taken out of the library. Taught by instructor Claire Kessinger Mathey, PHD. Perfect for getting into the Halloween spirit!

Registration is required. To register please contact James Trapasso at 914-941-2416 ext. 327 OR jtrapasso@wlsmail.org.

WHERE: Ossining Public Library, Conference Room (2nd floor)

WHEN: October 6th, 13th and 20th

WHAT TIME: 10:00-12:00pm


2. The Great Pumpkin Carving

The Great Pumpkin Carving Ossining

Start off at Bethany Arts Community in Ossining and carve your very own GREAT PUMPKIN LANTERN! Bring it home for your front door this Halloween. After you’ve carved your pumpkin at Bethany, head up to Croton-on-Hudson to Historic Hudson Valley’s Van Cortlandt Manor for The Great Jack O’Lantern BLAZE!! Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’ lanterns

WHERE: Bethany Arts Community

WHEN: October 23rd

WHAT TIME: 5:30pm

HOW MUCH: $35 includes: One (1) Pumpkin and carving kit/book Two (2) FREE Tickets for The Great Jack O’Lantern BLAZE

3. Forest O’ Fears

Halloween in Ossining

This one is not for the faint of heart: The Forest O’ Fears Haunted Attraction is an experience that will stimulate the senses. The unique location in Ossining NY, home of Sing Sing, has provided inspiration for this attraction. Watch out for escaped inmates and be careful not to get thrown in “old sparky.” After entering the NEW Garage of Terror you will head onto the tractor-drawn wagon of hay and be pulled into the dark forest where you will encounter monsters, witches, serial killers, zombies and more. This is a thrill ride for the holiday season that you should not miss. Forest O’ Fears offers rides on a 15-minute interval with a limit of 60 online tickets per ride. Space is limited, buy your tickets now to ensure your seat.

WHERE: Cedar Lane Park

WHEN: October 26 & 27

WHAT TIME: 6:00-10:00

HOW MUCH: Limited tickets are available at the gate for $20. You must bring your ticket with you to enter the event. You can get your tickets HERE

4. Halloween Village

Halloween Village

Thinking the Hayride may be a little scary for your gang? Not to worry. The Halloween Village will feature music by Ossining’s own Strange Hours and DJ Johnny G, food by 6 Degrees of Separation (who will also be selling seasonal beer and yes, that includes pumpkin!), games like Mummy Flush, Chip’s Pumpkin Fling and Franken-toss, and a fire show by Flaming Barrel of Monkeys Entertainment. The Ossining Athletic Booster Club and Gregory Perry Photography will be among the vendors on the field. Oh, and the “Unhaunted Hayride” and the Homespun Merry-Go-Round will thrill the littlest Halloween enthusiasts in your party.

WHERE: Cedar Lane Park

WHEN: October 26 & 27

WHAT TIME: 6:00-10:00

HOW MUCH: “Field access only” tickets will be available at the gate – $10 per adult, $5 per child, and each ticket comes with 5 passes for games on the field.

5. Halloween Kids and Pet Parade

Halloween Parade Ossining

The Parade will start at the Elks (118 Croton Ave) on Sat 10/27 at 11am and end at Mike Risko Music (144 Croton Ave), where there will be all kinds of vendors, activities for kids and pets, and contests for best costume!

WHERE: The Elks – Mike Risko

WHEN: Saturday October 27th

WHAT TIME: 11:00am


6. Halloween on Main Street

Halloween On Main Street Ossining

We’re calling on all ghosts and goblins, but especially all the superheroes, princesses, pirates, definitely The Incredibles, any pirates, unicorns, we assume there will be a few Fortnite characters doing that silly floss dance, all witches, Black Panthers, and for sure anyone with one of those inflatable dinosaur costumes! Do you wait all year for costumes and candy?! This is for you. We’re a little more than a week away! Wednesday, October 31st is Halloween and we’re hosting the biggest and baddest Halloween party in town! From 6-8pm Main Street will be the perfect place for kids (and even a few adults) to collect candy from stations staffed by local businesses and community organizations, dance the night away, grab a snack, and of course no party is complete without a bounce house. See you on Main Street!

WHERE: Main Street

WHEN: October 31st

WHAT TIME: 6:00-8:00pm


7. Take a Halloween Drive

Halloween in Ossining

All around town you’re going to be able to see houses decorated with the Halloween Spirit. Finish up dinner and take a drive around town with the kids. Costumes optional!

WHERE: Houses all around town

WHEN: October

WHAT TIME: Anytime but we recommend 20 minutes after sunset


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