For the third straight year, the famed Stockbridge estate known as Naumkeag has been transformed into a Halloween oasis.  

For the month of October, the Trustees of Reservations decorate a half-mile trail on this hillside property with flowers, lights, and over a thousand carved pumpkins to give visitors the ultimate New England Halloween experience. The Incredible Naumkeag Pumpkin Show is sold out this year, but have no fear — Connecting Point’s Brian Sullivan managed to get a ticket and takes us there. 


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Zydalis Bauer, Connecting Point: For the third straight year, the famed Stockbridge Estate known as Naumkeag has been transformed into a Halloween oasis.

For the month of October, the trustees of Reservations decorate the half-mile trail on this hillside property with flowers, lights, and over a thousand carved pumpkins to give visitors the ultimate New England Halloween experience known as the Incredible Naumkeag Pumpkin Show.

The event is sold out for this year, but have no fear — Connecting Point’s Brian Sullivan managed to get a ticket, and takes us there.

Brian Sullivan, Connecting Point: It’s early afternoon in late October on the eight-acre property in Stockbridge, Massachusetts, known as Naumkeag.

Right now, aside from the staff putting on some finishing touches for the pumpkin display, or some hanging carved jack o’ lanterns gently blowing in the breeze, all is quiet on this palatial estate.

But even for neighbors who’ve lived close by for decades, the scenery here is still something to behold.

Micheline Laguilhomie, Stockbridge Resident: This is a place it’s so beautiful that, you know…I mean, for a French person, you must understand that we have magnificent castles, but we necessarily don’t have such space. It’s amazing.

Brian Sullivan: It doesn’t take long, though, for that silent serenity to be replaced by the sounds of parents and children making their way along these pumpkin decorated paths.

This is, after all, the third annual Incredible Naumkeag Pumpkin show, this year featuring over 1,500 hand-carved pumpkins.

And while the carvings of Star Wars characters and a witch’s cauldron that boils over with smoke filled bubbles may be a big draw for the little ones, I suspect that it doesn’t take a lot of arm twisting to get the adults to come out this way.

Joanne Conroy, Stockbridge Resident: It’s wonderful. They have pumpkins and chrysanthemums, all fall colors. It’s gorgeous and they’re all through the grounds and they have extraordinary lighting.

Brian Sullivan: My first trek along the trails was during the daylight hours, so I still had a little time to soak in the natural beauty of this display before they turned on that extraordinary lighting.

What I like is the obvious Halloween spirit here, but there’s also a real fall vibe going on, and because of this location, there’s definitely an old New England feel to this place. As a first time visitor, I can understand why tickets sold out so quickly.

As day turns tonight, the transformation from New England autumn walk through the woods to the coolest trick-or-treating trail ever begins to take shape. That one time seemingly harmless kettle blowing out bubbles earlier in the day, has suddenly turned itself into something resembling a volcano by night. The very welcoming Chinese garden by day becomes a gothic playground as the daylight fades.

And none of this is by accident.

Brian Cruey, The Trustees of Reservations: It’s kind of two different experiences here, right?

We have our daytime experience, which we have a lot more younger families coming to, so they can see it in the day, get their kids home in bed before the sun goes down. So, we try to decorate that with a lot of horticulture, fall decoration, pumpkins, gourds.

And then the lights go out and you can’t see as much of that, but then you really get to enjoy the element of the lights that we hang around the property as well

Brian Sullivan: From across the farmland, we can see cars lining up to turn down the long driveway to 5 Prospect Hill Road. The erstwhile property of Joseph and Caroline Choate has now become something of a destination spot for visitors from near and far for several events throughout the year.

For the month of October, it turns itself into a sort of Halloween wonderland, and that’s thanks in no small part to the tireless efforts put forth by the Trustees.

Brian Cruey: Every year, we try to make it bigger, better, make it feel fresh and new for the people who are returning. And if you’re coming here for the first time, we want you to take away that Naumkeag and the Trustees is a place that you can come for fun, family entertainment, you know, no matter what the season.