Jamaica Plain Halloween Events 2026
Your guide to the best Halloween events in Jamaica Plain and nearby
Jamaica Plain counts down to spooky season with Halloween happenings that bring neighbours together around community centres and lively streets. Trick or treat traditions, masquerade-style costume gatherings, and hayrides give families and adults different ways to participate. Ghost tours and pumpkin carving events add a more mysterious layer as evening falls, while glowing lights brighten the route through local neighbourhoods. With its creative spirit and welcoming public spaces, Jamaica Plain makes Halloween feel social, expressive, and full of memorable activities.
Browse Halloween Near Jamaica Plain by Category
Halloween Food, Drink, and Parties
Strictly 21+ costume party featuring a cash prize costume contest.
Family-Friendly Fall Activities
Includes picking bag, orchard access, corn maze, and play areas.
Halloween Movies, Theater, and Entertainment
Youth theater classes concluding with a staged student production.
Haunted Experiences
Nightly walking tour exploring Boston's darkest historic and haunted sites.
Unique & Unusual Halloween Events
Narrated nighttime trolley tour exploring Boston's haunted sites and historic burying grounds.
Editor's Picks
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Ghosts & Gravestones Nightwalk Tour
· Boston
Narrated nighttime trolley tour exploring Boston's haunted sites and historic burying grounds.
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Boston Ghosts Haunted Tours
· Boston
Nightly walking tour exploring Boston's darkest historic and haunted sites.
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The Rocky Horror Picture Show 50th Anniversary Tour
· Boston
Screening in 4K with a live shadow cast and original cast appearances.
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Boston Halloween Bar Crawl
· Boston
Multi-venue crawl featuring waived covers, costume contests, and drink specials.
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The Salem Witch Trial Tour
· Salem
Historical walking tour covering the true events of the 1692 trials.
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Belkin Family Lookout Farm Fall Festival
· South Natick
Includes picking bag, orchard access, corn maze, and play areas.
Events Happening Soon
Jamaica Plain Halloween Events Map
See every Halloween event, haunted attraction, and pumpkin patch on one map.
