Middletown Family-Friendly Fall Activities 2026

37 family-friendly fall activities in Middletown and nearby.

Middletown families can find thrills this Halloween season. For a major attraction, consider LEGOLAND New York's Monster Mash Brick-or-Treating, a ticketed experience a short drive away.

If you prefer something closer to home and free, Halloween on the Green in Danbury offers a community gathering.

All Family-Friendly Fall Activities Around Middletown

Brick or Treat

Goshen 7 mi $$$

Features 10 candy stations, themed LEGO builds, and live monster shows.

Illustration of a small Ferris wheel, striped tents and a decorated booth with pumpkins on a grassy fairground in autumn (11th Annual Bountiful Harvest Celebration)

11th Annual Bountiful Harvest Celebration

Otisville 6 mi

Features farm-to-table dining and a celebrity cow milking competition.

Sandyston Trunk or Treat

Sandyston 24 mi Free

Community trunk-or-treat featuring costumes, candy, and trunk decorating prizes.

Boo at the Zoo

Bear Mountain 24 mi

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

Illustration of a red tractor pulling a wooden wagon of small costumed figures past pumpkins and autumn trees near a red barn (Open House on the Farm 2026)

Open House on the Farm 2026

Walden 15 mi Free

Free family event with farm animals, hayrides, tractors, and local vendors.

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

Croton 33 mi

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

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

Tarrytown 39 mi

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

Illustration of an orange tractor pulling a wooden hay wagon with costumed characters past pumpkins, trees and a red barn (Headless Horseman Children's Day)

Headless Horseman Children's Day

Ulster Park 37 mi

A toned-down Halloween experience designed for families with young children.

Illustration of glowing jack-o'-lanterns, candles, pumpkin seeds and small figures on a wooden table under string lights (Jack-O’-Lantern Experience at Skylands Stadium)

Jack-O’-Lantern Experience at Skylands Stadium

Augusta 27 mi $$

Walk-through spectacular featuring over 6,000 illuminated hand-carved jack-o'-lanterns.

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 29 mi $

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

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Demarest Farms Pumpkin Festival)

Demarest Farms Pumpkin Festival

Hillsdale 35 mi $

Pick pumpkins in the orchard with hayrides and playground access.

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

Tarrytown 40 mi $

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

Pumpkin Chunkin!

Ringwood 26 mi $$

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

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (Fall Festival and Trunk or Treat)

Fall Festival and Trunk or Treat

Sparta 31 mi Free

Costume celebration featuring food, games, and activities for families.

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

Yonkers 44 mi $$

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

Stony Hill Farms Maze Fun Park

Chester 47 mi $$

Features a 10-acre corn maze celebrating New Jersey's 250th anniversary.

Zoo Boo

Paramus 40 mi

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

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

Danbury 47 mi Free

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

Illustration of a pumpkin patch with orange pumpkins, a red wheelbarrow, a wooden farm stand and two scarecrow figures (Whippany Railway Museum Pumpkin Patch Train)

Whippany Railway Museum Pumpkin Patch Train

Whippany 43 mi $$

Round-trip heritage train excursion with pumpkin picking and decorating for children.

Boooo-mfield 5K

Bloomfield 47 mi $$$

Halloween-themed 5K race and block party supporting local student-athletes and parks.

Illustration of a giant pumpkin on a stand in a grassy field near striped booths with small figures and pumpkins (Halloween Spooktacular at Cross County Center)

Halloween Spooktacular at Cross County Center

Yonkers 46 mi

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

Illustration of two costumed figures in a festive autumn street at dusk with pumpkins, string lights and a glowing bonfire (Strut Your Mutt: Canine Halloween Costume Contest)

Strut Your Mutt: Canine Halloween Costume Contest

Montclair 44 mi Free

Annual canine costume contest and parade with prizes.

Illustration of striped booths with pumpkins and costumed figures on a town street with orange autumn trees (Jersey Cares Halloween Costume Drive)

Jersey Cares Halloween Costume Drive

Livingston 45 mi

Collects new and gently used Halloween costumes for New Jersey children.

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

Yonkers 45 mi Free

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

Illustration of an older person handing out candy to costumed children on a glowing neighborhood porch at dusk (Cornwall Halloween Spooktacular and Howl & Prowl Parade)

Cornwall Halloween Spooktacular and Howl & Prowl Parade

Cornwall 20 mi

10th Anniversary Spooktacular with Cornwallis Family Homestead

Illustration of two tiny costumed figures near a flag among tall golden cornstalks, with small farm houses and pumpkins (Wright Family Farm Corn Maze and Pumpkin Patch)

Wright Family Farm Corn Maze and Pumpkin Patch

Warwick 12 mi $$

Expansive 5-acre corn maze and pumpkin picking.

Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees (Pochuck Valley Farms Market and Deli)

Pochuck Valley Farms Market and Deli

Glenwood 14 mi Free

Pick-your-own fruits and pumpkins

Illustration of tiny clay musicians playing on a hay stage among pumpkins, bunting and striped booths in autumn (MyKingstonKids Halloween Fest & Parade)

MyKingstonKids Halloween Fest & Parade

Kingston 40 mi Free

Two-day festival with parade and Imagine Park

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 33 mi $$

Over 100 years of harvest tradition

Ort Farms Fall Festival

Pequannock Township 34 mi $

Extensive fall activities with pick-your-own options

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn (Legend of Sleepy Hollow Family Storytelling Event)

Legend of Sleepy Hollow Family Storytelling Event

Sleepy Hollow 38 mi $$

Costumed storyteller retelling 'The Legend of Sleepy Hollow'

Illustration of smiling ghost figures and a small costumed child beside pumpkins and paint cups on a wooden table (Halloween Craft Workshop & Scavenger Hunt)

Halloween Craft Workshop & Scavenger Hunt

New Paltz 27 mi $

Hands-on Halloween crafts and historic site scavenger hunt

Tranquillity Farms Fall Fest

Green Township 40 mi $$

U-Pick pumpkins and scenic hayrides.

Illustration of costumed children carrying pumpkin buckets along a winding path past glowing cottages at dusk (Palisades Center Trick-or-Treat Halloween Event)

Palisades Center Trick-or-Treat Halloween Event

West Nyack 34 mi Free

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

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 44 mi $$

1.25-mile forest run with Halloween-themed obstacles

Annual Children's Halloween Party

Hackensack 44 mi Free

FREE children's Halloween party with variety show and parade

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 45 mi $$

Spooktacular Oktoberfest with Halloween costumes and fall festival fun.

Explore More Categories

Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights

Food, Drink, and Parties

1 of 3 Small Bites at Collinwood: Soirée in the Mansion Tarrytown

Intimate Dark Shadows fan gathering featuring actress Kathryn Leigh Scott.

See all 3 parties & tastings →

Illustration of a small haunted cottage with glowing windows, ghosts, jack-o'-lanterns and a black cat under a pale moon

Haunted Experiences

1 of 19 Wallkill's Haunted Barn Middletown

Features three haunted attractions, bonfires, and scary movies under the stars.

See all 19 haunted attractions →

Illustration of a pumpkin character and a ghost performing on a small stage with red curtains before a costumed audience

Movies, Theater, and Entertainment

1 of 7 The Spirits of Sleepy Hollow Country Sleepy Hollow

Supernatural magic and conjurings communicating with legendary Sleepy Hollow spirits.

See all 7 shows & screenings →

Illustration of a Halloween town at dusk with glowing houses, pumpkins, floating ghosts and a witch flying past a full moon

Unique & Unusual

1 of 14 Create a Fall Pumpkin Centerpiece Workshop 2026 Middletown

Craft a fresh floral arrangement inside a ceramic pumpkin.

See all 14 unique events →

Find Family-Friendly Halloween Fun on Our Map!

See all trunk-or-treats, pumpkin patches, and kid-friendly events nearby.

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Middletown Halloween events map - Click to view interactive map

Frequently Asked Questions

What happens if rain washes out a family event we booked in Middletown?

Read the policy before buying: farms usually offer rain checks for another day that season rather than refunds, while ticketed indoor events run regardless. Light drizzle often means a gloriously empty farm, so don't auto-cancel. Keep one indoor backup, a museum day, library event, or home carving afternoon, planned for each outdoor weekend so the costume doesn't go to waste.

What are the best costume choices for kids attending outdoor Halloween events in Middletown?

Pick costumes that survive walking, climbing hay bales, and a bathroom trip in under two minutes: no floor-length hems, no masks that block vision, and nothing that can't fit a jacket underneath. Sneakers always beat costume shoes. Add reflective tape for evening events, and pack a backup shirt because face paint, snow cones, and petting zoos will find white fabric.

What hygiene plan makes petting zoos at Middletown farms less risky?

The rule: animals, then handwash, then food, in that exact order, every time. Use the farm's wash stations rather than sanitizer alone when hands touch animals or fences, keep pacifiers and sippy cups in the bag near animals, and don't let kids eat inside the enclosure. Strollers stay outside pens. It's two minutes of routine that prevents the classic post-farm stomach bug.

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