Ossining Halloween 2025

What to Expect This Halloween in Ossining!

Ossining halloween happenings center near Sing Sing and the Hudson River waterfront for eerie riverfront strolls. Enjoy haunted boat tours, costume parades and family fall festivals along the Main Street and waterfront parks.

Find the best Halloween events in Ossining this year!

Ossining Halloween Events

Ossining Family-Friendly Fall Activities (1)

Three smiling people, two women and one man wearing a hat, are gathered around carved pumpkins in front of a large, ornate building. A dinosaur figure with its mouth open is visible in the background, adding a festive and slightly spooky atmosphere.

Details

📍 Croton-on-Hudson, NY, US

(2.2 mi from Ossining)

The Great Jack O'Lantern Blaze

Over 7,500 illuminated, hand-carved pumpkins.

When

Friday, September 12, 2025

Event Details

👻 Scare Factor: 👻👻👻👻👻

💰 Budget: $$

🎃 Family Friendly: 🎃🎃🎃🎃🎃

⚡ Energy: Moderate

Event Description

Prepare to be amazed by The Great Jack O'Lantern Blaze, an immersive Halloween spectacle featuring over 7,000 hand-carved, illuminated pumpkins. Wander through themed lands, discover iconic New York landmarks sculpted from gourds, and marvel at a 'wickedly' fun emerald-hued dreamscape. This unforgettable event offers synchronized lighting, an original soundtrack, and unique attractions like pumpkin dinosaurs and a planetarium, making it a must-see fall attraction.

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pumpkin_carvingfamily_friendlypumpkin_patchfall_festivalhalloween_festival

⭐ Best For: Families, couples, halloween enthusiasts

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Ossining halloween_festival (1)

A young woman wearing a hat smiles as she holds a glowing jack-o'-lantern in a park at night, surrounded by many other carved pumpkins and silhouetted figures.

Details

📍 Briarcliff Manor, NY 10510

(2.7 mi from Ossining)

Halloween in Sleepy Hollow Country

The legendary home of the Headless Horseman

When

Wednesday, October 1, 2025

Event Details

👻 Scare Factor: 👻👻👻👻👻

💰 Budget: $$

🎃 Family Friendly: 🎃🎃🎃🎃🎃

⚡ Energy: Moderate to high

Event Description

Step into the legendary world of Sleepy Hollow Country for an unforgettable Halloween season. They offer a captivating array of events, from the mesmerizing Great Jack O’Lantern Blaze with thousands of illuminated pumpkins to spine-chilling ghost tours and dramatic retellings of 'The Legend of Sleepy Hollow.' Explore historic cemeteries, haunted attractions, and vibrant street fairs, all set against a backdrop steeped in folklore and autumn charm.

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⭐ Best For: Halloween enthusiasts, legend lovers, families

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Near Ossining

New City Halloween Events

A group of four people, two young girls and two young adults, are smiling and posing for a photo in a mall decorated for Halloween. The girls are wearing witch hats, and one is holding a pumpkin. The adults are also dressed in festive attire, and the man is holding a gift bag.

West Nyack

Details

Palisades Center Trick-or-Treat Halloween Event

Family-friendly trick-or-treat event at a large shopping center.

👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃

📏 6.7 miles from Ossining

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Greenburgh Halloween Events

Two cartoon children, a boy and a girl, walk through a graveyard at dusk, holding lanterns and a bucket, with tombstones and a blurred figure in the background.

Sleepy Hollow

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Classic Evening Lantern Tour

Two-hour lantern tour of historic Sleepy Hollow Cemetery

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 4.6 miles from Ossining

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A headless horseman in a witch hat rides a black horse through a spooky forest at night, surrounded by glowing jack-o'-lanterns and floating ghosts under a full moon.

Sleepy Hollow

Details

The Spirits of Sleepy Hollow Country

Supernatural magic show with legendary spirits

👻👻👻👻👻 💰 $$$ 🎃🎃🎃🎃🎃

📏 5.1 miles from Ossining

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See all 9 events in Greenburgh →

Peekskill Halloween Events

A smiling couple stands in a cornfield with pumpkins at their feet. The man wears a cowboy hat and plaid shirt, while the woman holds a large pumpkin.

Yorktown Heights

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Wilkens Fruit & Fir Farm Corn Maze and Fall Festival

Over 100 years of harvest tradition

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 8.1 miles from Ossining

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Three cartoon bears, two white and one brown, are carving pumpkins on a wooden table outdoors. They are surrounded by more pumpkins and autumn decorations, creating a festive Halloween atmosphere.

Bear Mountain

Details

Boo at the Zoo

Bear treats and Halloween enrichment activities.

👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃

📏 12.7 miles from Ossining

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White Plains Halloween Events

Two women play musical instruments on a stage decorated with numerous lit candles and red curtains, creating a warm and intimate atmosphere.

White Plains

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Candlelight: A Haunted Evening of Halloween Classics

Halloween classics performed by candlelight

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 10.2 miles from Ossining

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North Stamford Halloween Events

A group of cartoon children and lambs are on a farm with pumpkins and barns, celebrating Halloween.

39 Scofieldtown Rd

Details

Trick-or-Treat on Heckscher Farm

Members-only trick-or-treat with riddle hunt

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 16.6 miles from Ossining

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A woman in a blue denim jacket is sitting at a table with a tray of food, interacting with several dinosaurs in a farm-like setting with autumn foliage and a red barn in the background.

39 Scofieldtown Rd

Details

Fall Family Fest Sundays

Fall festival with a dinosaur twist

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 16.6 miles from Ossining

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Harrison Halloween Events

Three children, two boys and a girl, are gathered around a table filled with Halloween decorations, including pumpkins and skeleton figures. They are looking at a glowing blue orb placed in a bowl of snacks, with two framed Halloween-themed paintings on the wall behind them.

Rye

Details

Westchester Children's Museum Halloween Big Weekend Event

Not-so-scary Halloween celebration for young children

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 16.7 miles from Ossining

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Yonkers Halloween Events

A group of Halloween-themed toy figures, including a skeleton, a witch, and a ghost, are gathered around pumpkins and potion bottles, creating a festive and slightly spooky scene.

Yonkers

Details

Brick-or-Treat Monster Party

LEGO Monsters take over for a Monster Party

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 13.6 miles from Ossining

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Two cartoon children dressed as witches stand on a cobblestone street decorated for Halloween, holding jack-o'-lanterns and candy bags.

Yonkers

Details

Trick or Treating at Ridge Hill

Community trick-or-treating event for children

👻👻👻👻👻 💰 FREE 🎃🎃🎃🎃🎃

📏 13.8 miles from Ossining

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See all 5 events in Yonkers →

Mahwah Halloween Events

A smiling couple in cowboy hats and fall attire are sitting in a pumpkin patch, holding pumpkins. In the background, there are rows of pumpkins, a red barn, and trees with autumn foliage.

Mahwah

Details

Secor Farms Fall Festival

Hayrides to pumpkin patch and two corn mazes.

👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃

📏 15.1 miles from Ossining

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A couple in a wagon filled with pumpkins, surrounded by a cornfield and autumn trees, enjoying a fall harvest.

Mahwah

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Secor Farms Fall Activities

Scenic hayride to pumpkin patch and corn mazes.

👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃

📏 15.1 miles from Ossining

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Ridgewood Halloween Events

A young Black boy and a young girl sit in a wooden wagon filled with pumpkins, surrounded by a pumpkin patch and farm buildings under a partly cloudy sky.

Hillsdale

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Demarest Farms Pumpkin Festival

Pick-your-own pumpkins at a historic farm

👻👻👻👻👻 💰 $ 🎃🎃🎃🎃🎃

📏 15.2 miles from Ossining

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Two children, a boy and a girl, stand on a path decorated with glowing jack-o'-lanterns and miniature houses, under a string of festive lights, evoking a magical Halloween night.

Hillsdale

Details

Halloween Light Show at Demarest Farms

32-acre drive-through Halloween light show with synchronized audio.

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 15.3 miles from Ossining

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See all 3 events in Ridgewood →

Stamford Halloween Events

Three people in Halloween costumes, two women dressed as witches and one person in a skeleton mask, are holding drinks and smiling at an outdoor Halloween party with orange lanterns in the background.

Stamford

Details

The Official Halloween Bar Crawl Stamford

Two-day Halloween bar crawl with exclusive specials.

👻👻👻👻👻 💰 $$ 🎃🎃🎃🎃🎃

📏 18.3 miles from Ossining

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Last updated: 10/9/2025