Cumberland Family-Friendly Fall Activities 2026

36 family-friendly fall activities in Cumberland and nearby

Family-Friendly Fall Activities this weekend Oct 23–25

Sat24Oct Halloween Trunks-of-TreatsTaunton Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (Halloween Trunks-of-Treats) Sat24Oct Fall-o-ween on the FarmLincoln Illustration of a red tractor pulling a wooden wagon of small costumed figures past pumpkins and autumn trees near a red barn (Fall-o-ween on the Farm) Sat24Oct Pick or Treat Halloween Family FunNorthborough Illustration of costumed clay children and a witch playing among pumpkins, hay bales and tents on an autumn lawn (Pick or Treat Halloween Family Fun) Sat24Oct Truck or TreatShrewsbury Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees (Truck or Treat) Sun25Oct Winky Providence Monster Dash 5KProvidence Illustration of a Halloween costume contest on an outdoor stage with costumed figures, a ghost, a trophy and a watching crowd (Winky Providence Monster Dash 5K) Sun25Oct PruBoo 2026Boston Illustration of kids in costumes at a table with pumpkins, bowls of treats, and paper bats and bunting overhead (PruBoo 2026)

Other Halloween categories in Cumberland

Illustration of a Halloween party at dusk with costumed characters around a punch bowl, a ghost, pumpkins and string lights CumberlandHalloween Food, Drink, and Parties16 parties & tastings Illustration of a small haunted cottage with glowing windows, ghosts, jack-o'-lanterns and a black cat under a pale moon CumberlandHaunted Experiences16 haunted attractions Illustration of a pumpkin character and a ghost performing on a small stage with red curtains before a costumed audience CumberlandHalloween Movies, Theater, and Entertainment2 shows & screenings Illustration of a Halloween town at dusk with glowing houses, pumpkins, floating ghosts and a witch flying past a full moon CumberlandUnique Halloween Events10 unique events

About Family-Friendly Fall Activities in Cumberland

As Halloween approaches, Cumberland and surrounding areas host a spectrum of family celebrations. You'll find major ticketed attractions like the Jack O'Lantern Spectacular in Stockbridge, alongside community gatherings such as the free Weymouth's Halloween Trunk-or-Treat. From large-scale light displays to local farm festivals, each event offers a distinct way to mark the season. Consider what atmosphere suits your family, whether it's a drive for an expansive outdoor show or a neighborhood gathering.

Find Family-Friendly Halloween Fun on Our Map!

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

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Cumberland Halloween events map - Click to view interactive map
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