Get Spooked This Halloween at These Historical Trustees Homes

Featuring a ’20s-themed cocktail party, a yoga class with a twist, and so many pumpkins.

Photo provided by The Trustees

As Halloween floats closer each day, it brings with it a barrage of questions: Do you need a costume change for every party, what’s the magic number of candy bars for trick-or-treaters, what events are family-friendly, and most important of all: What’s actually scary? To answer all of the above and more, the Trustees of Reservations has orchestrated haunted happenings at several of their Massachusetts properties this month, from a 400 pumpkin jack-o-lantern display at a National Historic Landmark in the Berkshires to a hair-raising tour through a late poet’s old homestead. And though beautiful, these very old homes are the perfect places to revel in the year’s most haunted holiday.

With options from the northeast to the southwest, these historical sites are a unique way to embrace the Halloween spirit while also enjoying a new corner of the state.

The Incredible Naumkeag Pumpkin Show

We all recognize the Berkshires as one of the most beautiful places to peep leaves this time of year. But if you head over to Stockbridge this fall, you’ll catch hundreds of unexpected orange surprises amongst the foliage. The Trustees have lit up the grounds of the 44 room Gilded Age retreat with more than 400 hand-carved jack-o-lanterns (plus over 1,000 gourds and pumpkins), but they’ve also set up a “shire-inspired woodland village” for guests to explore. Throughout the month, live music and bonfire-browned s’mores will also be on offer at Naumkeag, as well as a night of trick-or-treating on October 31 (free for kids and Stockbridge residents).

Separate tickets are also being sold for a slew of other spooky activities, including a haunted house and a live-action version of the beloved board game Clue—this one is inspired by the life of the estate’s original 19th-century owner, attorney Joseph Choate. Mystery solvers must be 18+, and dressing up in 1920s garb is highly encouraged.

$9 for members or $15 for non-members, 4-8:30 p.m., Thursdays-Sundays, October 3-31, Naumkeag, 5 Prospect Hill Road, Stockbridge, MA.

Homestead Haunted House

Tread carefully as you wander through the woods and into the one-time home of American poet and newspaper editor William Cullen Bryant—twigs may snap underfoot, floorboards may creak unexpectedly, and scholarly ghosts may lurk about the 200-year-old property. Hold your breath as the tour ventures through the former servant’s quarters, up seldom-used back stairways, and around the third floor. Only the bravest should opt for this historical Halloween experience, and the Trustees advise against bringing along any children under the age of 12.

$7 for members or $12 for non-members, 6:30-9:30 p.m., Saturday, October 26, William Cullen Bryant Homestead, 216 Bryant Road, Cummington, MA.

Boos and Brews: Adult Pumpkin Trail

During the Nocturnal Animal Pumpkin Trail, costumed kids are welcome to roam around Stevens-Coolidge Place, the Colonial Revival home that originally belonged to one of North Andover’s founding families, using the self-guided walk to spot nocturnal critters. But earlier in the week, adults can leave the kids with a sitter and head to North Andover on their own for a night of enjoying the gardens, counting the pumpkins (there are 400 jack-o-lanterns in total), and pairing drinks and bites from on-site vendors.

$5 for members or $10 for non-members, 6-9 p.m., Thursday, October 24, Stevens-Coolidge Place, 1 Chestnut St., North Andover, MA.

The Cabinet of Dr. Caligari: A Castle Hill Halloween Party

If you missed the Crane Estate’s Roaring Twenties Lawn Party back in August, here’s a second chance: Clean the cobwebs from your flapper dress and make your way to the Great House atop Castle Hill, where an old-timey murder mystery cocktail party of sorts will unfold around you. Based on the silent horror film The Cabinet of Dr. Caligari, released in Germany in 1920, the mysterious affair will feature asylum director and hypnotist Dr. Caligari himself. Throughout the night, be on the lookout for deaths, a kidnapping, and plenty of custom cocktails making the rounds. And for anyone looking for a healthy refresher the morning after a night of madness, swing back around to the Crane Estate, where a “pumpkin yoga” class will take place in the barn. Novices and seasoned yogis alike are welcome to bend and stretch with help from an unconventional tool: pumpkins.

Halloween Party: $44 for members, $55 for non-members, 7-9 p.m., Saturday, October 26, Castle Hill on the Crane Estate, 310 Argilla Rd, Ipswich, MA.

Pumpkin Yoga: $24 for members, $30 for non-members, 10-11:30 a.m., Sunday, October 27, Castle Hill on the Crane Estate, 310 Argilla Rd, Ipswich, MA.

Adult Night! Halloween Owl Prowl

Leave out a bowl of candy with a “please take two sign” and drive over to the Fruitlands Museum, about 40 miles west of Boston. Rather than standing by the front door on Halloween night, this woodsy walk is an active (though decidedly less adorable) alternative to idly passing out candy. Naturalist Laurie Nehring will educate the adults-only group on some owl facts and calls, and then take them out into the woods around Fruitlands—a Trustees site once home to author Louisa May Alcott, and more recently used as a filming location for the new star-studded movie iteration of her book Little Women. The trek is under a mile long, but in that time hikers will try to catch the glowing eyes and flapping wings of the nocturnal owls soaring around the dark forest. And of course, post-hike fireside s’mores, wine, and beer are the quintessential autumn way to warm up inside and out. Though there are also family-friendly happenings taking place at Fruitlands the weekend before Halloween, this 21+ owl prowl is one of the coolest.

$12 for members, $20 for non-members, 7-10 p.m., Thursday, October 31, Fruitlands Museum, 102 Prospect Hill Road, Harvard, MA.