15 Halloween Activities Kids & Adults Will Love

From family-friendly pumpkin festivals to spine-tingling ghost tours 

Visiting the Berkshires in October? Get into the spirit of the spooky season with our guide to the best haunted houses, awesome costume parties, and the not-so-scary Halloween events of 2026. If you love all things Halloween, we’re here to help you plan a month of scary-good fun. Get started with this short list of spooktacular ideas—and consider booking in advance, these popular attractions get busy fast!

1. Ride on a vintage rail car to a pumpkin patch with Hoosac Valley Trains (or the more chilling ghost-story version just for adults).
2. Head to Jiminy Peak’s 13 Nights attraction for the super-creepy haunted house tour, eerie woodland walk, and thrilling nighttime Mountain Coaster ride.
3. Visit Hancock Shaker Village for the Pumpkin Extravaganza family day or spine-chilling Haunted Hancock tours.
4. Dress in a costume inspired by your favorite artwork in The Clark collection for free admission to Halloween at the Clark.
5. Join a guided ghost tour for bone-chilling tales of paranormal activity at Edith Wharton’s The Mount.
6. Attend the themed Masquerade Macabre Ball at Ventfort Hall Gilded Age Museum.
7. Bring the family to Ioka Valley Farm for PYO pumpkins, hayrides, and a mini corn maze (plus maple and pumpkin treats at the Calf-A Snack Bar).
8. Learn about owls, bats, spiders, and other iconic Halloween creatures on a Twilight Nature Walk at Mass Audubon Pleasant Valley Wildlife Sanctuary.
9. Create a fun costume for Pittsfield’s 80th themed Halloween parade: Futuristic Frights.
10. Contact the Berkshire County Historical Society for notable burial sites and cemeteries you can explore on a self-guided tour.
11. Build a Halloween-themed LEGO wreath with Bottomless Bricks at their October Brick & Sip party (18+).
12. Pick up your favorite sweets at Coco’s Candy, then wander Main St. past the ghoulish and goofy Halloween scenes painted on store windows by local students.
13. Join in the community spirit at the Mohawk Theater Haunted House tour.
14. Discover the magic of Naumkeag’s Incredible Pumpkin Show, where thousands of carved jack-o-lanterns light a walking trail through the landscaped grounds.
15. Add some altitude and adrenaline. Catamount Mountain Resort, Ramblewild and Berkshire East Mountain Resort have their own thrills which include scenic rides, ziplining and aerial adventures.

The Mount, Edith Wharton Cultural Center

Ready to plan a memorable Halloween in the Berkshires? In addition to all the frighteningly fun stuff going on, a getaway to the Berkshires in October also means beautiful fall landscapes, great restaurants serving seasonal farm-fresh fare, and plenty of comfy places to stay where you’re close to all the action (some of them are even haunted)!

For more seasonal events during your visit, check out our Events Calendar.