Happy Holidays in the Berkshires

‘Tis the season for merry making!

Get your friends and family together for these festive events, craft fairs, and other cheerful opportunities to get into the holiday spirit. Check out the following ideas for some season fun #intheberkshires of Western Massachusetts!

Note: Please be sure to check dates and times with each venue for accurate planning.

Norman Rockwell: Home for the Holidays
November 9, 2024 – February 25, 2024
On view November 4 through February 25, 2024. A heartwarming collection of the artist’s iconic holiday-themed works from Valentine’s Day, Independence Day to Thanksgiving, Christmas, and New Year’s. Renowned for his ability to capture the spirit and warmth of American life, Rockwell’s paintings in this exhibit reflect the joy, nostalgia, and togetherness of the holiday season.

Dressing the Christmas Tree at Bidwell House
November 21 at 4:00 pm
Presented by antiques expert Lorraine German, Dressing the Christmas Tree is a fascinating look at both antique and vintage Christmas decorations. Lorraine will discuss the history of adorning holiday greens from their pagan beginnings through the mid-20th century and will provide examples of ornaments from her own collection.

NightWood at The Mount
November 22 – January 4, 2025
NightWood is an innovative and immersive sound and light experience set against the backdrop of Edith Wharton’s historic home. Wander the illuminated 3/4-mile route through the woods and gardens for an otherworldly experience that evokes wonder and awakens the imagination.

Festival of Trees: Aquatica at Berkshire Museum
November 23 – January 5, 2024
Festival of Trees: Aquatica is on display in Berkshire Museum’s second floor November 23, 2024 – January 5, 2025. This year, the Museum celebrates the sea, river, and wetland animals that we all know and love as it builds a brand new aquarium coming in 2025. This event is free with admission. during regular hours (Monday to Saturday: 10 AM-5 PM; Sunday: 12 PM-5 PM). Opening reception is November 22 from 5:30 – 8:00 pm.

Tinseliner Christmas Scenic Train Rides
November 24-December 17, 2023
Santa will be visiting the Berkshires again this year and will join Berkshire Scenic Railway onboard their Tinseliner train for Christmas carols and good cheer.

Winterlights at Naumkeag
November 29 – January 4, 2024
Experience the sparkle of the holiday season as Winterlights returns to three special places: Stevens Coolidge House & Gardens in North Andover, Naumkeag in Stockbridge, and Eleanor Cabot Bradley Estate in Canton. Enjoy dazzling light displays, festive music, seasonal treats, and time with loved ones outside among the trees and snow.

North Adams Tree Lighting
November 27, 2024
On the evening before Thanksgiving, North Adams gears up for the holiday season with the annual Tree Lighting Ceremony and Hometown Holidays kick-off event! Join the crowd at 6:00 pm around the tree at Monument Square on Main Street as thousands of twinkling lights come to life. After the ceremony, Santa always makes a special visit with free goodie bags for the little ones.

LumiNAMA Lights
November 27, 2024 – January 3, 2025
Take in all the lights along the downtown loop of North Adams by walking down Main, Holden, Center and Eagle Streets this holiday season!

Festival of Trees – Cheshire
December 1, 2024
The Festival of Trees opens to the public Dec.1 at 4:30 p.m., at Cheshire Community House at 191 Church St. Hayrides to the tree lighting in the town Center will leave at 5:30 , and return at 6:30 p.m. for a celebration, with Santa, caroling, a bonfire and more.

Holiday Tea at Arrowhead
December 1 and December 15, 2024
Enjoy a tasty holiday tea in the historic parlors at Arrowhead, with 19th century readings and more. December 1 and December 15, 2024.

Lenox Tree Lighting and Winterland
December 2, 2024
The lighting of the Lenox tree will happen in Lilac Park at6:00 pm on December 2. Be seranaded by the Lenox Community Choir, and get a photo with Santa. Follow the link above for more events, including a fun run and student art show.

Sheffield Christmas Tree Lighting
December 3, 2023
Save the date for the community tree lighting, Dec. 3 at 5:30 p.m.

A Christmas Carol
December 5-22, 2024
See A Christmas Carol December 5-22, 2024 at Berkshire Theatre Group’s Unicorn Theatre, a Berkshire County holiday tradition. Revel in the joy and redemptive power of Christmas as told in the timeless tale of Ebenezer Scrooge, the infamous miser who is shown the error of his ways and reformed by four spirits. Journey back to Victorian England and experience the classic story filled with holiday carols and the wonderment of the season.

Berkshire Theatre Group’s A Christmas Carol, 2023. Photo by David Dashiell.

Stockbridge Main Street at Christmas
December 6-8, 2024
The town of Stockbridge, made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday wreaths and festive lights, as the town celebrates Stockbridge Main Street at Christmas. Sponsored by the Stockbridge Chamber of Commerce, the holiday celebration offers a full range of holiday activities for the entire family to enjoy. Capping off the weekend on Sunday the town reenacts the spirit of Norman Rockwell’s famous holiday scene Stockbridge Main Street at Christmas, complete with vintage automobiles parked in the spots occupied in the painting. The day’s activities are sure to delight the child in everyone.

Downtown Festive Frolic – Pittsfield
December 6-7, 2024
Friday, December 6: Tree lighting Ceremony at Park Square; Wreath Art Auction at Lichtenstein Center for the Arts; hot chocolate and pictures with the Grinch at Otto’s
Saturday, December 7: European Holiday Market on Duham Mall; Berkshire Bazaar by Thistle ‘n Thorn Floral at Holiday Inn; free children’s activities downtown; free kids’ Paint & Sip at St. Stephen’s; photo ops with Santa; holiday Where’s Winston? scavenger hunt kick-off

Pittsfield Christmas Tree Lighting
December 6, 2024
A chorus will sing holiday carols, and Santa and Mrs. Claus will make a special appearance after the tree is lit.

Williamstown 40th Annual Holiday Walk and Events
December 6-8, 2023
Enjoy holiday festivities with a traditional New England flair! Old-fashioned caroling, horse-drawn carriage rides, a Penny Social, Santa Claus, and much more, including the signature Reindog Parade! Dog owners are welcome to deck the hounds and join the fun.

Radiant Nights at Hancock Shaker Village
December 7-31, 2024
Radiant Nights at Hancock Shaker Village is a unique multisensory holiday experience where the Village will once again sparkle with more lights, farm animals, music, festive spirits, and holiday fun for the entire family.

Breakfast with Santa at Ioka Valley Farm
December 7 & 8, 2024
Have breakfast with Santa, 8:00 am – 12:00 noon, at Ioka Valley Farm.

Tinseliner Train, Hoosac Valley Train Rides

Berkshire Botanical Garden Holiday Marketplace
December 6-8, 2024
An eagerly awaited tradition continues at Berkshire Botanical Garden on Friday evening, Saturday and Sunday, Dec. 6-8 from 10:00 am – 4:00 pm, with Holiday Marketplace featuring the legendary Gallery of Wreaths. Select from a collection of 100 unique, one-of-a-kind designer wreaths as well as an assortment of holiday-blooming amaryllis and paperwhites in decorative and clay containers, succulent arrangements, garlands, hanging terrariums and gift items presented by regional artisan vendors.

Christmas at Chesterwood
December 8-22 (Fridays-Sundays)
Chesterwood announces the return of the annual Christmas at Chesterwood. Hear stories of the French Family’s Christmas traditions while visiting the historic Studio and ground floor of the Residence, decorated in style for the holidays. Includes complimentary hot cider and doughnuts.  Advanced purchase of timed tickets required, available on the half hour.

Annual Community Chanukah Celebration
December 29, 2024
The Jewish Federation of the Berkshires is hosting this Channukkah Celebration from 5:00-7:00 pm.

New Year’s Eve Ball Drop for Kids of All Ages
December 31, 2024
This is a kid-friendly event and free to the public! The ball will drop at 8:00 pm, rather than midnight, for all to enjoy and then still be able to make it to your New Year’s Eve gatherings.

Joyful Family Holidays
Various
Enjoy Joyful Family Holidays at the historic Red Lion Inn, a Main Street landmark for hospitality for 250 years.