If the television ads and store displays weren’t enough to warn you, the holiday season is already in full swing. Two special Trustees places—Naumkeag and the Eleanor Cabot Bradley Estate—are also getting in the seasonal spirit with their own tradition: Winterlights. But this annual hallmark of dazzling displays would not be possible without many dedicated Trustees staff and volunteers who spend long days outside in the crisp Fall air.

These teams are hard at work long before the first guests stroll through a tunnel of twinkling lights or sip hot cocoa under the stars. Whether it’s a short turnaround between seasonal events in the Berkshires or an ever-expanding endeavor South of Boston, the preparation for Winterlights blends creativity, logistics, and a patient love for creating that holiday magic.

A Short Turnaround in the Berkshires

When the calendar flips to November, it’s all hands on deck in the Berkshires. Trustees staff from every corner of the region congregate in Stockbridge to pack up decorations from The Incredible Naumkeag Pumpkin Show and begin unfurling strings of holiday lights. Pumpkins, cauldrons, and cobwebs are replaced with an estimated 200,000 bulbs spanning approximately 18 miles when strung end-to-end.

“It’s less than a month between our biggest shows of the entire year,” said Amanda Duquette, Trustees Properties Director in the Western Hills and Berkshires. “The massive scale wouldn’t be possible without our amazing staff plus many local volunteers who spend countless hours ensuring each season’s magic is on full display.”

With six years already under its belt, Naumkeag has the short transition down to a science. A whiteboard in the Carriage House—where many of the decorations are stored—neatly outlines the to-dos with assignments and strikethroughs for completed work. People continually bustle in and out from dawn to dusk (and beyond) in an organized chaos only achieved through years of practice.

“Each display is meticulously planned so we don’t blow a fuse, and every light you see is strung up by hand,” said Duquette. “But all the long days are worth it when you run into a starstruck guest shocked to a standstill by the dazzling lights.”

Ever-Expanding South of Boston

While there is a bit more time to set up the displays at the Eleanor Cabot Bradley Estate, the sheer quantity of bulbs and decorations is still daunting. Similar to the Berkshires, Trustees staff from across the South Shore descend on Canton with dozens of dedicated volunteers. They carefully craft displays through the trees, trails, and garden nooks of this 90-acre estate, utilizing approximately 150,000 bulbs that stretch nearly 15 miles across.

“We keep adding new lights—and changing displays—so it is fresh and exciting for our return visitors,” said Elena Gauthier, Trustees Regional Events Manager. “We also brought back many beloved features from past years, including rainbow road, candy cane lane, the gnome home, and a new scavenger hunt.”

Work began in early October with an inventory of the decorations, signage, and other materials. As one might expect, the weather plays a pivotal role in determining what survives each year. Every string of lights needs to be tested when it’s pulled out of storage, and bulbs are routinely replaced before they are sent to be strung up.

“Think how tricky it is figuring out why one string doesn’t light up in your home decorations this time of year, then multiply that by a thousand,” said Gauthier. “Our incredible team is hard at work making sure every bulb is bright and twinkling by Thanksgiving!”

See the culmination of everyone’s efforts at Winterlights in the Berkshires or South of Boston! Members receive special pricing!