Can't Miss Winter Events 2026

By Breanna Steele
December 26, 2025


In winter, the Berkshires settle into a peaceful hush as some animals hibernate and birds migrate south to escape the cold. Yet, the community embraces the frosty season, infusing the region with vitality through lively events featuring campfires, sled contests, and much more.

Here is a list of events to make your visit to the Berkshire truly unforgettable.

North Adams WinterFest
Downtown North Adams
Saturday Feb. 16 from 9 a.m. to 3 p.m. 

Downtown North Adams transforms into a winter wonderland with  a variety of activities for you and your family to enjoy. 

Explore the city on a horse drawn carriage ride, which will take you throughout the downtown area where you can participate in a craft fair, street hockey, children's games, and more.

Activities line-up here.

10 X 10 UpStreet Arts Festival
Various Pittsfield Venues
Feb. 12 through 22 

Pittsfield comes alive as the 10x10 Festival transforms the city into a vibrant playground of creativity. Over two thrilling weeks, experience an explosion of theater, music, visual arts, dance, and outdoor adventures.

Dive into the acclaimed 10x10 New Play Festival at Barrington Stage Company, indulge in A Taste of Downtown, explore dazzling mural exhibitions, watch the colorful display of fireworks, and celebrate at the lively winter festival—each event promising unforgettable moments.

List of events here

Pittsfield WinterFest
Clapp Park, Pittsfield 
Feb. 16 10 a.m. to 1 p.m.

Round up the whole family for a day packed with winter excitement! Zoom down snowy slopes in the cardboard sled contest, unleash your creativity in the snow sculpture competition, and jump into a variety of spirited games. 
Cap off the adventure by gathering around the campfire for gooey s'mores—guaranteed to make this winter break unforgettable for kids and grown-ups alike.

More information here.

ThunderFest
Adams Visitor Center, Adams
March 21
Enjoy a free festival filled with music, entertainment, food, and more. There are many kids activities like face painting and you can also enjoy a campfire with smores to warm you up. You can also enjoy a historic train ride by Berkshire Scenic Railway.

More information here.

Stockbridge Main Street Christmas 
Main Street, Stockbridge
Dec. 6 through 7

Main Street in Stockbridge transforms into a living Norman Rockwell painting, bursting with holiday magic. The town sparkles with festive lights and wreaths, while families enjoy cheerful activities, live music, historic property tours, and plenty more merry moments.

You can also visit the Norman Rockwell Museum to view many of his pieces, including the exhibit “Home for the Holidays” on view until Feb. 22

The exhibit is a collection of holiday themed works by Norman Rockwell—from Thanksgiving and Christmas to New Year’s.  More information here

Winterlights at Naumkeag
Naumkeag, Stockbridge
Nov. 28 though Jan. 3

Visit Naumkeag and view the thousands of lights strewn over the property. There is also food and drinks to warm you up while you walk. More information here

Berkshire Museum Festival of Trees
Hancock Shaker Village, Pittsfield
Nov 28 through Dec 28

Every Friday, Saturday, and Sunday, the historic Hancock Shaker Village will welcome visitors to gaze at more than 75 trees throughout the museum, culminating in a magical display in the Round Stone Barn.

This year there are more than 75 trees on display, 23 decorated by schools and 52 main entries across 42 organizations including banks, businesses, and nonprofits. 

More information here

Nightwood
The Mount, Lenox
Dec. 12, 13, 18-23, 26-31
 
The Mount has decked out its grounds for the annual Nightwood installation with lights and music to provide an immersive experience to its visitors. More information here