Salem Haunted Happenings Marketplace
A walkable downtown Salem circuit featuring curated artisan makers and food.
Family-Friendly Fall Activities Near Gloucester 2026
28 family-friendly fall activities near Gloucester.
Gloucester families can find Halloween happenings from local trick-or-treating to a drive to Stoneham for Stone Zoo Boo.
Events include indoor activities like the Boston Children's Museum Halloween celebration and outdoor farm visits.
All Family-Friendly Fall Activities Around Gloucester
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Food, Drink, and Parties
1 of 20
Boston Fenway Halloween Bar Crawl
Boston
Costumed pub crawl through bars around Kenmore Square and Lansdowne Street.
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Haunted Experiences
1 of 17
Salem Witch Museum October Events
Salem
Timed presentations and exhibits explore the 1692 Salem witch trials.
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Movies, Theater, and Entertainment
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Witches Amongst Us: A 1692 Experience
Salem, MA
Immersive, comical retelling of the Salem Witch Trials with audience interaction
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Unique & Unusual
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Festival of the Dead
Salem
Exploration of death's mysteries through diverse rituals and events
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Find Family-Friendly Halloween Fun on Our Map!
See all trunk-or-treats, pumpkin patches, and kid-friendly events nearby.
Frequently Asked Questions
Which weekend is best for family Halloween events in Gloucester?
The first weekend of October has full activities and the thinnest crowds; the two weekends before Halloween are wall-to-wall wagons. If you want the buzz, go peak; if you want photos without strangers in them, go early. Late September often means opening deals. For trunk-or-treats and costume parades, the weekend before Halloween is usually the only option, so book patches around it.
Are hayrides at Gloucester farms okay for babies and toddlers?
Daytime, non-spooky hayrides are generally fine from infancy if a lap adult holds the child the whole ride; wagons bounce hard over field ruts. Sit toward the center, away from wheel edges, and skip rides where kids sit on loose hay bales without sides. Evening "haunted" versions with actors are a different product, so check which one you're queueing for.
How do we make Halloween costumes work in cold or wet Gloucester weather?
Build the costume a size up over a thermal base layer, and choose designs where a coat reads as part of the look, capes, robes, and animal onesies win October. Face paint beats masks in drizzle, and clear ponchos exist for downpour parades. For evening events, add reflective tape and glow bracelets. Test the full layered outfit at home once before the night.