Woodstock Family-Friendly Fall Activities 2026

49 family-friendly fall activities in Woodstock and nearby

Illustration of a pumpkin patch full of orange pumpkins with two small farmers, red wheelbarrows and a farm stand (All Seasons Orchard Fall Festival)

All Seasons Orchard Fall Festival

Aug 29 – Nov 1

Woodstock $$

Features over 30 barnyard activities and a Dolly Parton corn maze.

Illustration of a ghost, a witch and a pumpkin figure on a dusk street with glowing houses, autumn leaves and pumpkins (Trunk or Treat at Trademark Events)

Trunk or Treat at Trademark Events

Sun, Oct 18

Woodstock Free

Free family gathering featuring decorated trunks, games, candy, and goodie bags.

Illustration of two costumed figures in a festive autumn street at dusk with pumpkins, string lights and a glowing bonfire (Santa's Village Pumpkin Patch and Fall Festival)

Santa's Village Pumpkin Patch and Fall Festival

East Dundee 18 mi

A complete fall makeover with pumpkin patches, mazes, and amusement rides.

Illustration of a ghost and a small witch carrying a pumpkin bucket on a sidewalk past glowing porches on an autumn street (Boo in the Barn at SOUL Harbour Ranch)

Boo in the Barn at SOUL Harbour Ranch

Sat, Oct 24

Barrington 17 mi $$

Freaky fundraiser featuring trick-or-treating and visits with therapy animals.

Boo at the Zoo

Oct 31 – Nov 1

West Dundee 15 mi $

Features trick-or-treating throughout the zoo and daily costume parades.

Lindberg Pumpkin Patch

Sep 11 – Oct 31

Caledonia 22 mi $

Northern Illinois fall farm featuring a 7-acre pumpkin patch and corn maze.

Illustration of toy goats, a pony and white ducks among pumpkins and hay in a fenced pen with two costumed children (Crystal Lake Trick or Treat Halloween Event)

Crystal Lake Trick or Treat Halloween Event

Sat, Oct 24

Crystal Lake 9 mi

Plaza trick-or-treating with magic shows, a petting zoo, and games.

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

Richardson Adventure Farm Corn Maze and Pumpkin Patch

Sep 12 – Nov 1

Spring Grove 16 mi $$

Home to the world's largest corn maze spanning 28 acres.

Illustration of a Halloween costume contest on a small stage with a pumpkin, robot, witch, ghosts, trophy and audience (Halloween Hustle 5K & Kids Dash)

Halloween Hustle 5K & Kids Dash

Sat, Oct 24

Palatine 25 mi $$$

Costume-themed 5K run/walk and Kids Dash benefitting the Boys & Girls Club.

Howl-O-Ween Dog Costume Event

Sat, Oct 24

Dadeville 21 mi Free

Canine costume contest featuring treats, prizes, and owner-pet coordination.

Goebbert's Farm Teen Trip

Sat, Sep 26

South Barrington 22 mi $$$

Fall farm trip for teens featuring a corn maze and entertainment.

Illustration of a glowing ferris wheel and carousel at dusk with pumpkins, jack-o'-lanterns and small costumed figures (Schaumburg Halloween Carnival)

Schaumburg Halloween Carnival

Oct 16 – Oct 31

Schaumburg 27 mi $$

Classic carnival with a Halloween twist

Illustration of a pumpkin patch with many orange pumpkins, curling vines, a wheelbarrow and a small farm stand at dusk (The Great Highwood Pumpkin Festival)

The Great Highwood Pumpkin Festival

Oct 2 – Oct 4

Highwood 34 mi Free

Features massive pumpkin walls, community carving, carnival rides, and costume contests.

Illustration of a fall festival street with big pumpkins in front, striped booths, and small figures under orange trees (Sycamore Pumpkin Festival)

Sycamore Pumpkin Festival

Oct 21 – Oct 25

Sycamore 26 mi

Community celebration featuring over 1,000 decorated pumpkins, carnivals, and a giant parade.

Illustration of clay figures walking past striped market stalls and pumpkins on a paved square with orange autumn trees (Howl-O-Ween Canine Costume Contest)

Howl-O-Ween Canine Costume Contest

Sat, Oct 24

Buffalo Grove 27 mi Free

Features a doggy egg hunt alongside a creative pet costume competition.

Illustration of a ghost and two costumed kids trick or treating past glowing houses with pumpkins and autumn leaves at dusk (Tricks & Treats in the Valley)

Tricks & Treats in the Valley

Oct 24 – Oct 25

Schaumburg 28 mi $

Half-mile trick-or-treat trail past historic farm buildings and woods.

Illustration of tiny clay musicians playing on a hay stage among pumpkins, bunting and striped booths in autumn (Happy Times Pumpkin Fest at Didier Farms)

Happy Times Pumpkin Fest at Didier Farms

Sep 16 – Oct 31

Lincolnshire 27 mi $$

Chicagoland's fall tradition at Didier Farms

Halloween Hayday

Sat, Oct 24

Geneva 31 mi $

Features a costume contest, bounce houses, Mad Scientist, and hayrides.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (Kroll's Fall Harvest Farm)

Kroll's Fall Harvest Farm

Sep 19 – Oct 31

Waukegan 29 mi $

Educational corn maze, hayrides, petting zoo, and pre-picked pumpkin patch.

Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (Halloween Fun Fest 2.0 & Parade)

Halloween Fun Fest 2.0 & Parade

Sat, Oct 24

Bartlett 26 mi

Costume parade, downtown trick-or-treating, and a haunted art gallery.

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (All Hallows' Eve at Midway Village)

All Hallows' Eve at Midway Village

Sat, Oct 24

Rockford 27 mi $

Trick-or-treat across more than 20 decorated historic Victorian buildings.

Illustration of a twilight carnival with a glowing ferris wheel, a carousel, a game booth, pumpkins and costumed figures (Kishwaukee Family YMCA Halloween Bash 2026)

Kishwaukee Family YMCA Halloween Bash 2026

Fri, Oct 16

Sycamore 28 mi $

Features both a standard and a not-so-scary haunted house.

Illustration of cars with open trunks decorated with pumpkins and balloons, with a child figure beside an orange car at dusk (Truck or Treat at Porter Park)

Truck or Treat at Porter Park

Sat, Oct 17

Roscoe 28 mi

Touch-a-truck meets trunk-or-treating with emergency vehicles and local food trucks

Illustration of a town square fall festival with striped pumpkin booths, costumed figures, and orange autumn trees (Autumn Harvest Fest at Spring Valley Nature Center)

Autumn Harvest Fest at Spring Valley Nature Center

Sun, Oct 4

Schaumburg 28 mi $

Experience 19th-century farm life demonstrations and seasonal harvest activities.

Illustration of costumed children carrying pumpkin buckets along a winding path past glowing cottages at dusk (East Troy Railroad Museum Trick or Treat Trains)

East Troy Railroad Museum Trick or Treat Trains

Oct 9 – Oct 30

East Troy 33 mi $$

Costume train ride featuring trick-or-treating, park games, and pumpkin picking.

Pumpkin Walk

Sat, Oct 3

Buffalo Grove 27 mi $

Stroll a nature path illuminated by over 100 lighted pumpkins.

Trick or Treat Trail

Fri, Oct 30

Buffalo Grove 27 mi Free

No-scare candy trail with friendly characters, games, and live entertainment.

Illustration of a Halloween craft scene with clay kids, a friendly ghost, bats and glowing pumpkins under party bunting (Coyote Crossing Mini Golf - Not So Scary Golf)

Coyote Crossing Mini Golf - Not So Scary Golf

Mon, Oct 12

West Chicago 31 mi

Scare-free family mini golf featuring costumes, tricks, and treats.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Spooktacular Halloween at Anderson Japanese Gardens)

Spooktacular Halloween at Anderson Japanese Gardens

Sat, Oct 24

Rockford 31 mi $

Family-friendly Halloween celebration partnered with Hoo Haven Wildlife Rehab & Education Center.

Illustration of a row of cars with open trunks decorated for Halloween at sunset with balloons, pumpkins and costumed kids (Kenosha YMCA Trunk or Treat)

Kenosha YMCA Trunk or Treat

Sat, Oct 24

Kenosha 34 mi Free

Trick-or-treat from creatively decorated trunks in the parking lot.

Halloween 3K Fun Run

Fri, Oct 23

Northbrook 35 mi

Costumed 3K run and walk featuring themed activities and costume contests.

Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (Family Night Trick-or-Treating)

Family Night Trick-or-Treating

Fri, Oct 23

Wheaton 35 mi

Costume walking tour featuring candy stations, entertainment, and teal pumpkins.

Illustration of an orange tractor pulling a wooden hay wagon with costumed characters past pumpkins, trees and a red barn (Play Date: Adventure Train and Pumpkin Day)

Play Date: Adventure Train and Pumpkin Day

Sat, Oct 10

East Troy 33 mi $$

Hosted family train ride and orchard hayride to the pumpkin patch.

Paddock Lake Halloween Party

Sat, Oct 24

Elkhorn 27 mi Free

Features a trunk-or-treat hosted by the Paddock Lake Ward.

Oak Lawn Trunk or Treat

Wed, Oct 28

Medinah 29 mi Free

Free trick-or-treating among creatively decorated themed car trunks.

Pumpkin Volcanoes

Fri, Oct 2

Waukegan 31 mi $

Decorate pumpkins and watch them erupt like volcanoes.

Illustration of a corn maze path with tall golden cornstalks, small costumed figures, a flag, pumpkins and a red barn (Windy Acres Farm Fall Festival)

Windy Acres Farm Fall Festival

Sep 12 – Nov 1

Geneva 31 mi $$

Geneva farm festival featuring a corn maze, petting zoo, and rides.

Illustration of a candlelit ofrenda altar with marigolds and skull decorations as clay figures stand in a plaza at dusk (Sugar Skull Decorating Workshop)

Sugar Skull Decorating Workshop

Sat, Oct 3

Waukegan 32 mi $

Decorate your own calavera de azúcar to take home.

Northbrook Autumnfest

Sat, Oct 3

Northbrook 35 mi Free

Free community fall festival with classic activities

Illustration of a red tractor pulling a wooden wagon of small costumed figures past pumpkins and autumn trees near a red barn (Jonamac Orchard Pumpkin Patch)

Jonamac Orchard Pumpkin Patch

Malta 35 mi $$

Hayrides transport visitors directly out to the pumpkin patch on weekends.

Illustration of costumed figures beside a table with two gold trophies on a hay covered stage with pumpkins and string lights (Halloween Boo-wling Spooktacular)

Halloween Boo-wling Spooktacular

Hoffman Estates 21 mi $

Halloween bowling with crafts and costume contest

Stade's Farm & Market Fall Festival

McHenry 12 mi $$

Nine weekends of family fun with over 40 attractions

Pumpkin Splash

Hoffman Estates 21 mi $

Swim through a pumpkin patch to find your own pumpkin.

Illustration of costumed children and a cat walking a leafy sidewalk past glowing jack-o'-lanterns and cozy houses at dusk (Elgin Police Department's Halloween Extravaganza)

Elgin Police Department's Halloween Extravaganza

Elgin 21 mi $

Trick-or-treat at the police department

Goebbert's Fall Festival

South Barrington 22 mi $$

Iconic 'Happy Jack' fiberglass pumpkin landmark

Tom's Farm Market Fall Festival

Huntley 10 mi $

All-day fall festival with unique nighttime maze and hayride.

Des Plaines Trunk or Treat

Des Plaines 34 mi $

Trick-or-treating from decorated car trunks

Spook the Blocks

Rockford 33 mi Free

Trick-or-treating at over 30 downtown businesses

Illustration of a row of cars with open trunks decorated for Halloween at sunset with balloons, pumpkins and costumed kids (Trunk or Treat at Hidden Creek AquaPark)

Trunk or Treat at Hidden Creek AquaPark

Highland Park 34 mi Free

Kids trick-or-treat from decorated car trunks.

Family-Friendly Fall Activities this weekend Oct 23–25

Fri23Oct Sycamore Pumpkin FestivalSycamore

Fri23Oct Halloween 3K Fun RunNorthbrook

Fri23Oct Family Night Trick-or-TreatingWheaton

Sat24Oct Boo in the Barn at SOUL Harbour RanchBarrington

Sat24Oct Crystal Lake Trick or Treat Halloween EventCrystal Lake

Sat24Oct Halloween Hustle 5K & Kids DashPalatine

Other Halloween categories in Woodstock

Illustration of clay figures in costumes and a floating ghost at a Halloween party with a punch bowl and glowing pumpkins

WoodstockHalloween Food, Drink, and Parties2 parties & tastings

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and a black cat among bare trees at twilight

WoodstockHaunted Experiences20 haunted attractions

Illustration of a small character with arms raised on a stage with red curtains, glowing lanterns and a pumpkin audience

WoodstockHalloween Movies, Theater, and Entertainment4 shows & screenings

Illustration of white ghosts floating over houses with glowing windows and pumpkins, with a witch flying past a full moon

WoodstockUnique Halloween Events4 unique events

About Family-Friendly Fall Activities in Woodstock

Woodstock families can find Halloween fun throughout October, from downtown gatherings to attractions in nearby towns. Explore events across various locations, some requiring admission and others offering free community participation.

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Halloween Events Near Me

49 family-friendly fall activities in Woodstock and nearby

Family-Friendly Fall Activities this weekend Oct 23–25

Other Halloween categories in Woodstock

About Family-Friendly Fall Activities in Woodstock

Find Family-Friendly Halloween Fun on Our Map!