For the past few years, 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.  

If you couldn’t make it this year, have no fear — Connecting Point’s Brian Sullivan brings us there. 

This segment originally aired on October 29, 2021.


Read the full transcript:

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. 

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.

And while the carvings of Star Wars characters and witch’s cauldron that boils over with smoke filled bubbles may be a big draw for the little ones, I suspect 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. 

As day turns to night, 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.