See all Pittsfield Halloween happenings this year!
Pittsfield kicks off Halloween 2025 near the main district and historic Park Square with ghostly tours and frightful events throughout October. Halloween offerings include Halloween adventures, autumn gatherings and supernatural fun featuring pumpkin carving, haunted walks and family-friendly festivals.
Find the best Pittsfield Halloween happenings this year!
Top Halloween In and Around Pittsfield
- Pittsfield Halloween Parade
- Naumkeag Pumpkin Show (Stockbridge)
- Depot After Dark: Teen Dance Party Edition
- Berkshire Scenic Railway Museum Halloween Train Ride (Adams)
- 13 Nights at Jiminy (Hancock)
- The Mount Ghost Tours (Lenox)
- Field of Horrors (Troy)
- Fright Fest at Six Flags New England (Agawam)
- Nightmare Acres (South Windsor)
- DementedFX Haunted House (Holyoke)
See even MORE Halloween events below!
Pittsfield Halloween
Pittsfield Family-Friendly Fall Activities
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Naumkeag estate in Stockbridge, Massachusetts, transforms into a breathtaking autumn spectacle with its annual Pumpkin Show. Wander through enchanting displays featuring over 1,500 illuminated jack-o'-lanterns, complemented by hundreds of vibrant mums and gourds. The event offers expanded hours, including special early access daytime slots for a more serene experience, making it a must-visit fall attraction.
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All aboard for a spooky-fun, family-friendly Halloween Train Ride! Departing from Adams, MA, this festive journey offers scenic views of the Berkshire region with a touch of railroading history. Passengers are encouraged to wear costumes and embrace the holiday spirit on this approximately 60-minute adventure.
Pittsfield Haunted Experiences
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Dare to enter The Plantation of Jericho at 13 Nights at Jiminy, an outdoor haunted attraction set on a farm with a sinister past. Originally built to ward off an unknown menace, this location has become a place of chilling truths and sensory shocks. Prepare for a terrifying journey where darkness holds secrets too frightening to ignore.
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Step into the shadows of Edith Wharton's historic home for a chilling ghost tour. Guides lead you through darkened halls, sharing tales of reported eerie encounters, spectral shapes, and unexplained sounds. Decide for yourself if the creaking floors and slamming doors are mere imagination or something more.
Pittsfield Other Halloween Activities
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The historic Pittsfield Halloween Parade, a cherished community tradition since the mid-1940s, continues to bring the spooky spirit to life. This year's 'Haunted Hometown Spooktacular' theme encourages participants to draw inspiration from the parade's nearly 80-year history of elaborate floats and creative costumes. Watch as Tyler Street transforms into a festive route for this beloved annual event.
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Get ready for Depot After Dark: Teen Dance Party Edition! This event is exclusively for Berkshire County high school students, offering a fun and safe night out. Enjoy music from a live DJ, get creative with complimentary glitter and glow face painting, and show off your Halloween spirit with encouraged costumes. Beverages will be available for purchase, and adult chaperones will be present to ensure a great time.
Halloween Near Pittsfield
Albany Halloween
Troy Halloween
Holyoke Halloween
Springfield Halloween
Schenectady Halloween
Enfield Halloween
West Hartford Halloween
Hartford Halloween
Bristol Halloween
East Hartford Halloween
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Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
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