Ossining Family-Friendly Fall Activities 2026

41 family-friendly fall activities in Ossining and nearby

Illustration of glowing carved jack o'lanterns, candles, and small figures with tools on a wooden table under string lights (The Great Jack O'Lantern Blaze)

The Great Jack O'Lantern Blaze

Sep 18 – Nov 8

Croton

Walk through over 7,000 hand-carved, illuminated jack o' lanterns.

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Halloween Nightfair)

Halloween Nightfair

Sat, Oct 24

South Norwalk 24 mi Free

South Norwalk street festival with live entertainment, vendors, and trick-or-treating.

Illustration of a fall festival in a town square with a red roofed gazebo, striped booths, pumpkins and orange trees (Tarrytown Halloween Parade & Block Party)

Tarrytown Halloween Parade & Block Party

Sat, Oct 24

Tarrytown 6 mi

Parade featuring over 130 marching groups, floats, and costumed characters.

Illustration of a candlelit ofrenda altar with marigolds and skull decorations as clay figures stand in a plaza at dusk (Spooky Garden Nights at New York Botanical Garden)

Spooky Garden Nights at New York Botanical Garden

May 23 – Nov 2

Bronx 21 mi $$

A diverse calendar of seasonal events and exhibitions.

Boo at the Zoo

Sep 26 – Nov 1

Bronx 22 mi

Daytime Halloween celebration featuring costume parades, magic shows, and pumpkin displays.

Illustration of a clay kid in cat ears at a craft table with ghosts, pumpkins, paint pots and paper bats (LEGOLAND Discovery Center Westchester Brick or Treat)

LEGOLAND Discovery Center Westchester Brick or Treat

Oct 1 – Oct 31

Yonkers 14 mi $$

LEGO monster builds, glow-in-the-dark workshops, and a 4D movie.

SUP Witches Festival

Sat, Oct 10

Sleepy Hollow $

Costumed witches and warlocks paddleboard on the Hudson River with live entertainment.

Zoo Boo

Oct 16 – Oct 18

Paramus 19 mi

Fundraiser featuring trick-or-treating plus friendly or haunted train rides

Pick-Your-Own Pumpkins

Fri, Oct 2

Yorktown Heights 8 mi Free

Hudson Valley pumpkin patch with free admission and no reservations needed.

Illustration of a small clay figure on a path between tall golden cornstalks, with a red flag, pumpkins and a tiny cottage (Secor Farms Fall Hayrides and Pumpkin Picking)

Secor Farms Fall Hayrides and Pumpkin Picking

Mahwah 15 mi $

Scenic hayride past willow trees to pumpkin picking and corn mazes.

Illustration of a giant pumpkin on a stand in a grassy field near striped booths with small figures and pumpkins (Demarest Farms Pumpkin Festival)

Demarest Farms Pumpkin Festival

Sat, Sep 26

Hillsdale 15 mi $

Pick pumpkins in the orchard with hayrides and playground access.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Halloween on the Green)

Halloween on the Green

Sat, Oct 31

Danbury 24 mi Free

Costume parade, contest prizes, and goodie bags for costumed children.

Illustration of a ghost and two costumed kids trick or treating past glowing houses with pumpkins and autumn leaves at dusk (Lyndhurst Trick-or-Treat Weekend)

Lyndhurst Trick-or-Treat Weekend

Oct 17 – Oct 18

Tarrytown 8 mi $

Family-friendly trick-or-treating along estate pathways with optional self-guided mansion exploration.

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees (Revolutionary Harvest Festival)

Revolutionary Harvest Festival

Sat, Sep 19

Yonkers 16 mi Free

Free American Revolution festival featuring living history reenactors, music, and colonial games.

Illustration of a fall festival with a tractor, striped pumpkin booths, hay bales and orange trees (Halloween Spooktacular at Cross County Center)

Halloween Spooktacular at Cross County Center

Sat, Oct 24

Yonkers 16 mi

Features live stage shows, trick-or-treating, inflatable attractions, and photo ops.

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (Trick or Treating at Ridge Hill)

Trick or Treating at Ridge Hill

Sat, Oct 24

Yonkers 14 mi Free

Free trick-or-treating at participating shops and restaurants, rain or shine.

Illustration of a witch in a pointed hat reading a book in an orange armchair beside pumpkins, a lamp and black cats (Beasties and Besties Halloween Festival)

Beasties and Besties Halloween Festival

Sat, Oct 24

Norwalk 23 mi

Museum-wide haunted festival featuring shadow puppetry and a costume parade.

Boo at the Zoo

Oct 24 – Oct 25

Bear Mountain 13 mi

Features a costume parade, pumpkin decorating, and Halloween animal enrichment.

Pumpkin Chunkin!

Oct 17 – Nov 1

Ringwood 25 mi $$

Carve or decorate a pumpkin and launch it from a trebuchet.

Illustration of a craft table with a glitter pumpkin, paint cups, a clay kid, a smiling ghost and a paper bat under bunting (Family Halloween Day at Philipse Manor Hall)

Family Halloween Day at Philipse Manor Hall

Sat, Oct 31

Yonkers 16 mi Free

Sleepy Hollow movie marathon, crafts, and trick-or-treating in costume.

Illustration of a fall festival street with big pumpkins in front, striped booths, and small figures under orange trees (The Pumpkin Singalong at Sakura Park)

The Pumpkin Singalong at Sakura Park

Sun, Oct 25

New York 25 mi Free

Free outdoor community concert featuring four youth and community choirs.

Harvest Festival

Sun, Oct 18

New York 27 mi Free

Pumpkin picking, decorating, a Spooky Trail, and a live family concert.

Pumpkin Smash

Sun, Nov 1

Astoria 29 mi Free

Smash your leftover pumpkins to turn them into compost for local soil.

Bronx Zoo Harvest Glow

Bronx 22 mi $$

Illuminated Jack O’ Lantern Trail and Dinosaurs at Night

Illustration of a ghost, a witch and a pumpkin figure on a dusk street with glowing houses, autumn leaves and pumpkins (Cornwall Halloween Spooktacular and Howl & Prowl Parade)

Cornwall Halloween Spooktacular and Howl & Prowl Parade

Cornwall 21 mi

10th Anniversary Spooktacular with Cornwallis Family Homestead

Legend of Sleepy Hollow Family Storytelling Event

Sleepy Hollow $$

Costumed storyteller retelling 'The Legend of Sleepy Hollow'

Illustration of a pumpkin patch with many orange pumpkins, a scarecrow, a wheelbarrow, a fence and a red barn at sunset (Wilkens Fruit & Fir Farm Corn Maze and Fall Festival)

Wilkens Fruit & Fir Farm Corn Maze and Fall Festival

Yorktown Heights 8 mi $$

Over 100 years of harvest tradition

Illustration of two tiny figures on a gravel path among golden cornstalks and pumpkins, with a red flag at sunset (Wright Family Farm Corn Maze and Pumpkin Patch)

Wright Family Farm Corn Maze and Pumpkin Patch

Warwick 25 mi $$

Expansive 5-acre corn maze and pumpkin picking.

Illustration of a winding path through autumn trees with glowing lanterns and carved pumpkins in purple evening light (Run Wild Halloween Costume Run)

Run Wild Halloween Costume Run

Scarsdale 11 mi $$

1.25-mile forest run with Halloween-themed obstacles

Illustration of tiny clay musicians playing on a hay stage among pumpkins, bunting and striped booths in autumn (Annual Children's Halloween Party)

Annual Children's Halloween Party

Hackensack 22 mi Free

FREE children's Halloween party with variety show and parade

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (New Settlement's Halloween Block Party)

New Settlement's Halloween Block Party

Bronx 22 mi Free

Free community Halloween celebration with games and resources

NICE Festival

Norwalk 23 mi Free

Connecticut's premier multicultural festival with two stages and 50+ international vendors.

Illustration of a small Ferris wheel, striped tents and a decorated booth with pumpkins on a grassy fairground in autumn (Creepy Crawlies in the Woods)

Creepy Crawlies in the Woods

Larchmont 15 mi Free

Not-too-spooky woodland exploration for families

Illustration of clay figures raising foamy beer steins at wooden tables under a striped tent with pumpkins and leaves (Spooktacular Oktoberfest at Trailside Nature Museum)

Spooktacular Oktoberfest at Trailside Nature Museum

Cross River 16 mi $$

Spooktacular Oktoberfest with Halloween costumes and fall festival fun.

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (New Canaan Halloween Block Party)

New Canaan Halloween Block Party

New Canaan 19 mi Free

Community block party for young trick-or-treaters

Howl-o-ween Event

Bronx 20 mi $

Pet costume showcase for Halloween

Illustration of a ghost and a small witch carrying a pumpkin bucket on a sidewalk past glowing porches on an autumn street (Palisades Center Trick-or-Treat Halloween Event)

Palisades Center Trick-or-Treat Halloween Event

West Nyack 7 mi Free

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

Illustration of a town square fall festival with striped pumpkin booths, costumed figures, and orange autumn trees (Halloween on the Harlem Meer Pumpkin Flotilla)

Halloween on the Harlem Meer Pumpkin Flotilla

New York 26 mi Free

New York's largest pumpkin flotilla on the Harlem Meer.

Ort Farms Fall Festival

Pequannock Township 27 mi $

Extensive fall activities with pick-your-own options

Illustration of a witch in an armchair reading a book to small children, with pumpkins and black cats nearby (Spooky City Halloween at the Museum of the City of New York)

Spooky City Halloween at the Museum of the City of New York

New York 26 mi $$

Halloween activities within a museum setting

Illustration of a Halloween parade on a street with a smiling pumpkin float, costumed children and orange balloons overhead (Riverside Park Pup Halloween Parade)

Riverside Park Pup Halloween Parade

New York 26 mi Free

Dog costume parade and contest

Family-Friendly Fall Activities this weekend Oct 23–25

Sat24Oct Halloween NightfairSouth Norwalk

Sat24Oct Tarrytown Halloween Parade & Block PartyTarrytown

Sat24Oct Halloween Spooktacular at Cross County CenterYonkers

Sat24Oct Trick or Treating at Ridge HillYonkers

Sat24Oct Beasties and Besties Halloween FestivalNorwalk

Sat24Oct Boo at the ZooBear Mountain

Other Halloween categories in Ossining

Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights

OssiningHalloween Food, Drink, and Parties11 parties & tastings

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk

OssiningHaunted Experiences16 haunted attractions

Illustration of a pumpkin character and a ghost performing on a lit stage with red curtains before a crowd at night

OssiningHalloween Movies, Theater, and Entertainment9 shows & screenings

Illustration of a Halloween town at twilight with glowing houses, jack o lanterns, ghosts, and a witch flying past the moon

OssiningUnique Halloween Events12 unique events

About Family-Friendly Fall Activities in Ossining

Halloween in the Ossining area offers numerous family activities, from large-scale immersive experiences like the Great Jack O'Lantern Blaze in nearby Croton-on-Hudson to local gatherings. Consider events spread across Westchester and beyond, including opportunities closer to home in towns like Sleepy Hollow and Tarrytown.

If you seek a free community event, look for those specifically noted as such. For those preferring a drive, attractions in the Bronx or Danbury provide additional choices, each with its own Halloween atmosphere.

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Halloween Events Near Me

41 family-friendly fall activities in Ossining and nearby

Family-Friendly Fall Activities this weekend Oct 23–25

Other Halloween categories in Ossining

About Family-Friendly Fall Activities in Ossining

Find Family-Friendly Halloween Fun on Our Map!