Pleasant Prairie Family-Friendly Fall Activities 2026

48 family-friendly fall activities in Pleasant Prairie and nearby

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 Free

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

Boo at the Zoo

Sat, Oct 24

Racine 15 mi $

Safe outdoor trick-or-treating alongside zoo animals, crafts, and bounce houses.

Illustration of a pumpkin patch full of orange pumpkins with two small farmers, red wheelbarrows and a farm stand (The Great Highwood Pumpkin Festival)

The Great Highwood Pumpkin Festival

Oct 2 – Oct 4

Highwood 25 mi Free

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

Illustration of a corn maze path with tall golden cornstalks, small costumed figures, a flag, pumpkins and a red barn (Swan's Pumpkin Farm - 50th Anniversary Season)

Swan's Pumpkin Farm - 50th Anniversary Season

Franksville 17 mi

Thousands of carving and cooking pumpkins with free farm admission

Fall at the Farm - Jerry Smith Farm

Sep 12 – Nov 1

Kenosha 5 mi $$

Family-owned farm featuring a six-acre corn maze, bounce pads, and pumpkins.

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 10 mi $

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

Jack-O'-Lantern Nights

Oct 1 – Oct 31

Racine 15 mi $

Paved zoo stroll filled with custom jack-o'-lanterns and festive uplighting.

Illustration of a ghost, a witch and a pumpkin figure on a dusk street with glowing houses, autumn leaves and pumpkins (A Spooktacular 5K - Trick or Trunk)

A Spooktacular 5K - Trick or Trunk

Sat, Oct 24

Mt Pleasant 12 mi $$

Night 5K Glow Run with Trunk or Treat

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 small cars parked at sunset with orange balloons, tiny houses on their roofs, a pumpkin and string lights (Special Needs Trunk-or-Treat)

Special Needs Trunk-or-Treat

Sun, Oct 25

Kenosha 5 mi Free

An inclusive trunk-or-treat celebration designed for children with special needs.

Pumpkin Volcanoes

Fri, Oct 2

Waukegan 11 mi $

Decorate pumpkins and watch them erupt like volcanoes.

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (Fall Festival Open House at The Learning Experience - Oak Creek)

Fall Festival Open House at The Learning Experience - Oak Creek

Sat, Sep 26

Oak Creek 24 mi $

Classroom games, pumpkin voting, treats, and a local silent auction.

Illustration of two clay kids and cotton ghosts around a craft table with painted pumpkins, paint pots and paper bats (Fall Pumpkin Candle Making Workshop)

Fall Pumpkin Candle Making Workshop

Fri, Nov 6

Racine 14 mi $$$

Craft a wooden pumpkin dough bowl candle with seasonal fall scents.

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 14 mi $

Decorate your own calavera de azúcar to take home.

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Oak Creek Fall Festival)

Oak Creek Fall Festival

Sat, Oct 24

Oak Creek 24 mi

Outdoor harvest celebration featuring hayrides, a petting zoo, and pumpkin decorating.

Jack-O-Lantern Jubilee

Sat, Oct 24

Milwaukee 34 mi Free

Dazzling Halloween Village with magical seasonal displays

Night of 1,000 Jack-o'-Lanterns

Oct 7 – Oct 25

Glencoe 29 mi $$

Features 75 giant 150-pound pumpkins, live carving, and costumed performers.

Boo at the Zoo

Oct 16 – Oct 24

Milwaukee 33 mi $$

Daytime and evening Halloween fun featuring animal pumpkin enrichment and trick-or-treating.

38th Annual Halloween Haunts

Oct 15 – Oct 17

Franklin 26 mi $$

Enchanted Forest with costumed characters and hundreds of Jack-o'-lanterns

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 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 26 mi $$

Chicagoland's fall tradition at Didier Farms

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 28 mi $$

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

Harvest Fest

Sep 12 – Oct 25

Mukwonago 29 mi Free

Old-fashioned harvest fun with apple picking, hayrides, and a corn maze.

West Allis Harvest Fair

Oct 2 – Oct 4

West Allis 33 mi $

Fall festival featuring pumpkin bowling, lumberjack shows, and State Fair treats.

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (The Hill Has Eyes Not So Scary Halloween Party)

The Hill Has Eyes Not So Scary Halloween Party

Oct 4 – Oct 25

Milwaukee 26 mi $

Family-friendly daytime trick-or-treat guided tour through haunted attractions.

Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (Fall Family Fest & Trunk or Treat)

Fall Family Fest & Trunk or Treat

Sat, Oct 3

Greenfield 28 mi Free

Local companies and vendors hand out candy to trick-or-treaters.

Illustration of a ghost and two costumed kids trick or treating past glowing houses with pumpkins and autumn leaves at dusk (East Troy Railroad Museum Trick or Treat Trains)

East Troy Railroad Museum Trick or Treat Trains

Oct 9 – Oct 30

East Troy 29 mi $$

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

Harvest Fest

Sep 12 – Oct 25

East Troy 29 mi $$

Ride historic electric shuttle trains between East Troy and The Elegant Farmer.

Illustration of clay goats, a duck and costumed figures among pumpkins and hay beside a small wooden shelter in daylight (Crystal Lake Trick or Treat Halloween Event)

Crystal Lake Trick or Treat Halloween Event

Sat, Oct 24

Crystal Lake 30 mi

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

Pumpkin Walk

Sat, Oct 3

Buffalo Grove 26 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.

Halloween 3K Fun Run

Fri, Oct 23

Northbrook 31 mi

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

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 31 mi $$$

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

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Milwaukee Public Market Harvest Festival)

Milwaukee Public Market Harvest Festival

Sat, Oct 10

Milwaukee 33 mi

A full day of fall fun at Milwaukee Public Market.

Illustration of a fall festival street with big pumpkins in front, striped booths, and small figures under orange trees (Bluemel's Annual Fall Fest)

Bluemel's Annual Fall Fest

Sat, Oct 17

Greenfield 28 mi Free

An in-person autumn gathering featuring food and family activities.

Apple Days

Sun, Oct 4

Muskego 27 mi Free

Fall gathering featuring live rock covers, bounce houses, and seasonal treats.

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 29 mi $$

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

Illustration of costumed children and a cat walking a leafy sidewalk past glowing jack-o'-lanterns and cozy houses at dusk (Trunk or Treat at Trademark Events)

Trunk or Treat at Trademark Events

Sun, Oct 18

Woodstock 31 mi Free

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

Illustration of cars with open trunks decorated with pumpkins and balloons, with a child figure beside an orange car at dusk (Paddock Lake Halloween Party)

Paddock Lake Halloween Party

Sat, Oct 24

Elkhorn 32 mi Free

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

Northbrook Autumnfest

Sat, Oct 3

Northbrook 30 mi Free

Free community fall festival with classic activities

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees (October 3 "Halloween Fun" First Fridays)

October 3 "Halloween Fun" First Fridays

Racine 14 mi $

Halloween-themed First Friday with free pumpkins and face painting.

Downtown Racine Candy Crawl

Racine 14 mi Free

Free candy crawl and Halloween scavenger hunt

Illustration of toy goats, a pony and white ducks among pumpkins and hay in a fenced pen with two costumed children (Stade's Farm & Market Fall Festival)

Stade's Farm & Market Fall Festival

McHenry 19 mi $$

Nine weekends of family fun with over 40 attractions

Illustration of two costumed figures in a festive autumn street at dusk with pumpkins, string lights and a glowing bonfire (Free Fall Family Fun Fest)

Free Fall Family Fun Fest

Racine 14 mi Free

Annual costume contest and parade with prizes.

Halloween Skelebration

Glenview 33 mi $$

Fright-free indoor/outdoor Halloween bash for kids

Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (West Allis Downtown Halloween Hunt)

West Allis Downtown Halloween Hunt

West Allis 32 mi Free

Community-wide trick-or-treating with over 20 businesses

Illustration of cars with open trunks decorated as tiny haunted houses with pumpkins and costumed kids at dusk (Trunk or Treat at Hidden Creek AquaPark)

Trunk or Treat at Hidden Creek AquaPark

Highland Park 27 mi Free

Kids trick-or-treat from decorated car trunks.

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (Justin Roberts & the Not Ready for Naptime Players: Trick or Treat! A Halloween Show)

Justin Roberts & the Not Ready for Naptime Players: Trick or Treat! A Halloween Show

Highland Park 28 mi $

Family Halloween show with trick-or-treating

Family-Friendly Fall Activities this weekend Oct 18–18

Sun18Oct Boo at the ZooMilwaukee

Sun18Oct Trunk or Treat at Trademark EventsWoodstock

thru1Nov Fall at the Farm - Jerry Smith FarmKenosha

thru1Nov Richardson Adventure Farm Corn Maze and Pumpkin PatchSpring Grove

thru25Oct Harvest FestMukwonago

thru25Oct Harvest FestEast Troy

Other Halloween categories in Pleasant Prairie

Illustration of a Halloween party at dusk with a ghost above string lights, two witches by a table, and glowing pumpkins

Pleasant PrairieHalloween Food, Drink, and Parties12 parties & tastings

Illustration of a small haunted cottage with glowing windows, ghosts, pumpkins and a black cat under a big pale moon

Pleasant PrairieHaunted Experiences12 haunted attractions

Illustration of a small ghost and a jack-o'-lantern performing on a stage with red curtains, watched by a crowd at dusk

Pleasant PrairieHalloween Movies, Theater, and Entertainment3 shows & screenings

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

Pleasant PrairieUnique Halloween Events6 unique events

About Family-Friendly Fall Activities in Pleasant Prairie

Pleasant Prairie families can find Halloween activities across several nearby towns. Events range from the extensive Racine Zoo Halloween Celebration to the Great Highwood Pumpkin Festival, offering diverse experiences for all.

Consider the family-focused trick-or-treating opportunities or, if you're looking for a drive, events like Halloween on the Square in Woodstock await.

Find Family-Friendly Halloween Fun on Our Map!

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

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Pleasant Prairie Halloween events map - Click to view interactive map

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Halloween Events Near Me

48 family-friendly fall activities in Pleasant Prairie and nearby

Family-Friendly Fall Activities this weekend Oct 18–18

Other Halloween categories in Pleasant Prairie

About Family-Friendly Fall Activities in Pleasant Prairie

Find Family-Friendly Halloween Fun on Our Map!