Wilmette Family-Friendly Fall Activities 2026

Wilmette $$

Family Halloween fun with inflatables, hayrides, pumpkin decorating, and a costume contest

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (Central Street Trick Or Treat)

Central Street Trick Or Treat

Evanston

Features neighborhood trick-or-treating, fall selfies, crafts, and a DJ dance party.

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 10 mi Free

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

Illustration of a ghost, a witch and a pumpkin figure on a dusk street with glowing houses, autumn leaves and pumpkins (Downtown Evanston Trick or Treat Stroll)

Downtown Evanston Trick or Treat Stroll

Evanston Free

Free trick-or-treating at local businesses with a fall photo backdrop.

Illustration of glowing jack-o'-lanterns, candles, pumpkin seeds and small figures on a wooden table under string lights (Night of 1,000 Jack-o'-Lanterns)

Night of 1,000 Jack-o'-Lanterns

Oct 7 – Oct 25

Glencoe 6 mi $$

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

BOO-seum Bash

Sun, Oct 25

Chicago 11 mi $$

Family Halloween fun featuring animal encounters, owl pellet dissection, and crafts.

Lincoln Square Apple Fest

Oct 2 – Oct 4

Chicago 8 mi $

Autumn celebration with fresh Midwest apples, cider, live music, and family entertainment.

Jack's Pumpkin Pop-Up

Sep 19 – Nov 1

Chicago 12 mi

Features downtown Chicago's only corn maze and over 10,000 pumpkins.

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

Lincoln Scared & Ravenswoooood Trick-or-Treat

Sun, Oct 25

Chicago 8 mi Free

Business district trick-or-treating and pumpkin decorating for costumed kids.

Lincoln Park Zoo Fall Fest

Sep 25 – Nov 1

Chicago 11 mi Free

Free harvest festival featuring animal enrichment, rides, and pumpkin carving.

Oaktoberfest

Sep 25 – Sep 26

Oak Park 13 mi Free

Free festival featuring live music, local food, and craft beer.

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

BooPalooza and BarkPalooza

Sat, Oct 17

Chicago 11 mi Free

Community festival featuring all-ages and dog costume parades, music, and games.

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

Northcenter Halloween Trick-or-Treat

Sat, Oct 31

Chicago 8 mi

Trick-or-treat across the town square and neighborhood storefronts.

Illustration of two costumed figures in a festive autumn street at dusk with pumpkins, string lights and a glowing bonfire (Roscoe Village Halloween Block Party)

Roscoe Village Halloween Block Party

Sun, Oct 18

Chicago 9 mi

Family-oriented street celebration with live music, photo ops, and candy.

Spooktacular Trunk-or-Treat

Oct 24 – Oct 25

Chicago 11 mi

Neighborhood trick-or-treating at local businesses across Lincoln Park.

Pumpkin Fest at Cosley Zoo

Oct 1 – Oct 31

Wheaton 24 mi $

Thousands of pumpkins line the zoo lawn alongside daily scavenger hunts.

Hamilton Boo Bash

Chicago 9 mi

Features a costume parade, carnival games, and a student-hosted haunted house.

Fall Fest at Oak Park

Sun, Sep 27

Oak Park 14 mi Free

Carnival rides, live bats and skunks, and pumpkin carving demonstrations.

Harvest Fest

Medinah 18 mi Free

Annual community festival featuring live music, hayrides, games, and food trucks.

Halloween 3K Fun Run

Fri, Oct 23

Northbrook 6 mi

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

Trick or Treat Trail

Fri, Oct 30

Buffalo Grove 13 mi Free

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

Pumpkin Walk

Buffalo Grove 14 mi $

Stroll a nature path illuminated by over 100 lighted pumpkins.

Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees (10/16: Spooktacular Halloween Stroll)

10/16: Spooktacular Halloween Stroll

Wheaton 24 mi $

Evening zoo stroll featuring seasonal decorations and pumpkin decorating.

Halloween Hoopla

Park Ridge 8 mi

Family scarecrow stuffing, pumpkin carving, campfire s'mores, and hayrides.

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Haunt on Hirsch Street – Family Block Party)

Haunt on Hirsch Street – Family Block Party

Melrose Park 13 mi Free

Free family block party with Halloween displays and train rides

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn (Monster Fun Halloween Wristband)

Monster Fun Halloween Wristband

Sat, Oct 31

Lombard 21 mi $$

Unlimited indoor attractions and free parkwide trick-or-treating in costume.

Trick or Treat Trail

Carol Stream 24 mi

A 1.1-mile trick-or-treat trail featuring games, candy, and a bouncy house.

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (Norwood Park Fall Fest)

Norwood Park Fall Fest

Chicago 7 mi Free

Free autumn festival featuring games, a candy hunt, and a pumpkin patch.

Illustration of small purple clay characters carving glowing jack-o'-lanterns on a wooden table with candles and seeds (Family Pumpkin Carving Party)

Family Pumpkin Carving Party

Fri, Oct 23

Melrose Park 13 mi $

You carve the pumpkin and park staff handles the cleanup.

Halloween Hoot and Howl

Fri, Oct 2

River Forest 14 mi Free

Family event featuring pumpkin painting and live music.

Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (C1 Fall Carnival and Trunk or Treat)

C1 Fall Carnival and Trunk or Treat

Chicago 7 mi Free

Features trunk-or-treating, a chili cook-off, and carnival games.

Illustration of small costumed figures and a witch playing on a sunny lawn with pumpkins, hay bales, a tent and orange trees (Hands-On Family Spooky Snacks and Sweet Treats)

Hands-On Family Spooky Snacks and Sweet Treats

Sat, Oct 31

Chicago 7 mi $$$

Kids and adults cook festive savory bites and sweet treats together.

Illustration of glowing jack-o'-lanterns, candles and scattered seeds on a wooden table under string lights at dusk (Pumpkin Carving & Painting at Midwest Coast Brewing Company)

Pumpkin Carving & Painting at Midwest Coast Brewing Company

Thu, Oct 29

Chicago 13 mi $$$

Includes a pumpkin, carving supplies, paint, and your first drink.

Illustration of small costumed figures and a witch playing on a sunny lawn with pumpkins, hay bales, a tent and orange trees (Spooktacular Fun Night)

Spooktacular Fun Night

Fri, Oct 30

Westmont 23 mi Free

Free family games, crafts, and silly fun with Wacky Drac.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (Autumn Equinox Celebration)

Autumn Equinox Celebration

Tue, Sep 22

Wheaton 25 mi Free

Outdoor nature play, crafts, and family activities celebrating fall's arrival.

Pumpkin Spice Pilates

Fri, Oct 9

Chicago 8 mi $$

Mat Pilates session followed by a seasonal pumpkin drink.

Boo Bash

Thu, Oct 15

Wheaton 24 mi $

A low-sensory Halloween event designed for neurodiverse children and families.

Northbrook Autumnfest

Northbrook 6 mi Free

Free community fall festival with classic activities

Pumpkin Smash & Bash

Sat, Nov 7

Park Ridge 8 mi Free

Roll, smash, and launch pumpkins into compost piles at Centennial Sled Hill.

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 25 mi $

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

Monster Madness

Sat, Oct 17

Lisle 27 mi $$

Festive autumn fun fair for children with games, inflatables, and hayrides.

Howl-O-Ween Dog Costume Event