Cheshire Family-Friendly Fall Activities 2026

36 family-friendly fall activities in Cheshire and nearby

Family-Friendly Fall Activities this weekend Oct 23–25

Sat24Oct West Hartford Halloween StrollWest Hartford Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (West Hartford Halloween Stroll) Sat24Oct Día de Muertos Community CelebrationHartford Illustration of clay skeleton figures in folk outfits by an altar with lit candles, orange marigolds and paper banners (Día de Muertos Community Celebration) Sun25Oct Mountain Mist Halloween HarvestMeriden Illustration of a miniature carnival at dusk with a glowing ferris wheel, a small carousel, game booths and jack-o'-lanterns (Mountain Mist Halloween Harvest) Sun25Oct Spooktacular on the GreenGuilford Illustration of a giant pumpkin on a stand in a grassy field near striped booths with small figures and pumpkins (Spooktacular on the Green) Sun25Oct Shubert Theatre Free Family Fun DayNew Haven Illustration of costumed children carrying pumpkin buckets along a winding path past glowing cottages at dusk (Shubert Theatre Free Family Fun Day) thru1Nov Bishop's Fall FestivalGuilford Illustration of a pumpkin patch with many orange pumpkins, a scarecrow, a wheelbarrow, a fence and a red barn at sunset (Bishop's Fall Festival)

Other Halloween categories in Cheshire

Illustration of clay figures in costumes and a floating ghost at a Halloween party with a punch bowl and glowing pumpkins CheshireHalloween Food, Drink, and Parties10 parties & tastings Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and a black cat among bare trees at twilight CheshireHaunted Experiences18 haunted attractions Illustration of a small character with arms raised on a stage with red curtains, glowing lanterns and a pumpkin audience CheshireHalloween Movies, Theater, and Entertainment7 shows & screenings Illustration of a Halloween town at dusk with glowing houses, pumpkins, floating ghosts and a witch flying past a full moon CheshireUnique Halloween Events7 unique events

About Family-Friendly Fall Activities in Cheshire

Cheshire has over 40 family-friendly Halloween events happening. From lively festivals like the Chuck E. Cheese Boo-tacular Halloween Event to free community gatherings such as Halloween on the Green in Danbury, there are many ways to celebrate.

Consider the bustling atmosphere of downtown Milford's Hall-O-Weekend, or the agricultural charm of Lyman Orchards Pumpkin Festival. Indoor and outdoor activities abound, catering to various preferences across the county.

Find Family-Friendly Halloween Fun on Our Map!

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

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Cheshire Halloween events map - Click to view interactive map
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