Happy Holidays in the Berkshires

‘Tis the season for merry making!

Gather your friends and family 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 22, 2025 – February 22, 2026
On view November 22 through February 22, 2025. A heartwarming collection of the artist’s iconic holiday-themed works from Thanksgiving and Christmas to New Year’s. Renowned for his ability to capture the spirit and warmth of American life, Rockwell’s paintings reflect the joy and nostalgia of the season as inspired by classic tales, holiday festivities and greetings, and the artist’s unique brand of gentle humor.

NightWood at The Mount
November 21, 22, 26, 28,29
December 6, 12, 13, 18-23, 26-31
January 2-3, 2026
Inspired by the natural world, NightWood combines cinematic music, theatrical lighting, and scenic elements to create encounters that evoke wonder, delight, and mystery throughout the forest and gardens of Edith Wharton’s Home. The NightWood Café will be serving drinks and seasonal treats in the Mansion courtyard. The bookstore will be open for holiday shopping.

Festival of Trees: Barn to Be Wild!
Friday, Saturday, and Sundays November 21 – December 28, 2025
Festival of Trees: Barn to be Wild! is a collaboration between Berkshire Museum and Hancock Shaker Village. Hosted by Hancock Shaker Village, come view trees decorated by different Berkshires-based organizations and businesses designed around the theme in a fun and unique way, celebrating the animals on the farm.
 
Berkshire Grown Winter Market 
November 22 at 10 am – Housy Dome, Great Barrington
November 23 at 10 am – GreylockWorks, North Adams
Berkshire Grown’s Winter Farmers Markets bring farmers and makers from Berkshire County and the surrounding region.

Hoosac Valley Train Rides

Tinseliner Christmas Scenic Train Rides
November 29, 30
December 6, 7, 13, 14
Santa will be visiting the Berkshires again this year!  The Tinseliner includes a ride on our festively decorated train with holiday music. The Tinseliner features festive decorations and joyful music during a scenic journey through the Hoosac Valley. Kids can write letters to Santa Claus, then meet him and (on most dates) Mrs. Claus in person to receive a special gift!

Winterlights at Naumkeag
November 28 – January 3, 2026
Wednesdays-Sundays from 4:30-9:00 pm
Experience the sparkle of the holiday season as Winterlights returns to Naumkeag. Enjoy dazzling light displays, festive music, seasonal treats, and time with loved ones outside among the trees and snow.

North Adams Tree Lighting
November 26, 2025
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 26, 2025 – January 3, 2026
Take in all the lights along the downtown loop of North Adams by walking down Main, Holden, Center and Eagle Streets this holiday season!

Adams Holly Days
November 30 – December 6
Kick off the holiday season at the Town of Adams’ annual tree lighting on November 30, featuring hay rides, festive music, hot chocolate, and treats with Mr. and Mrs. Claus. The celebration continues all week with town-wide events, including the Tinseliner Scenic Christmas Train, a Craft Fair, and the Holly Days festivities. Visit the website for details on each day’s programming.

A Christmas Carol
December 4-21, 2025
Gather your loved ones and join us for one of Berkshire County’s most cherished holiday traditions—A Christmas Carol, the timeless tale that continues to warm hearts and inspire audiences of all ages. Check the website for specific days and times.

The Nutcracker Ballet
December 5-7
The Albany Berkshire Ballet will perform that epic battle between giant mice and wooden princes called “The Nutcracker” at the Colonial Theater in Pittsfield. See the website for times and tickets.

Berkshire Art Show and Holiday Sale
December 5, 2025 from 5-7 pm – Cocktail Party
December 6, 2025 from 10 am – 5 pm
Kick off the weekend with an evening of art, conversation, and holiday cheer; shop all day for one-of-a-kind gifts created by our talented faculty artists.

Lenox Tree Lighting
December 5, 2025
The lighting of the Lenox tree will happen in Lilac Park at 6:00 pm on December 5. Community caroling at 5:45 pm, and get a photo with Santa.

Pittsfield Christmas Tree Lighting
December 5, 2025
The Pittsfield High School Chorus will perform a variety of carols around 5:45 p.m. before the ceremony begins, and Santa & Mrs. Claus will arrive following the tree lighting.  Additionally, two artists, Peter Vacchina and Robert Markey, will be creating holiday-themed ice sculptures in the park during the event. Their live ice sculpting will start before the ceremony and continue throughout the evening for attendees to watch, subject to favorable weather conditions. Those planning to attend the ceremony are asked to bring non-perishable food items that will be donated to the Christian Center’s food pantry.

Downtown Festive Frolic – Pittsfield
December 5-6, 2025
Friday, December 5: Tree lighting Ceremony at Park Square;  hot chocolate and pictures with the Grinch at Otto’s
Saturday, December 6: Berkshire Bazaar by Thistle ‘n Thorn Floral at Holiday Inn 11-4 pm; free kids’ Paint & Sip at St. Stephen’s; photo ops with Santa at Dunham Mall; Wreath Art Auction at Lichtenstein Center for the Arts at 4 pm. Check the link as additions are being made.

Williamstown Annual Tree Lighting and Holiday Walk
December 5-6, 2025
Enjoy holiday festivities with a traditional New England flair! Tree lighting  December 5 at Sweetwood of Williamstown at 4 pm. On December 6, join us for 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. Check the website for a complete list of activities.

Berkshire Botanical Garden Holiday Marketplace
December 5-7, 2025
An eagerly awaited tradition continues at Berkshire Botanical Garden with Holiday Marketplace featuring the legendary Gallery of Wreaths. Wreath Preview Party is December 5 form 5-7 pm;  Marketplace runs 10 am – 4 pm Saturday and Sunday, with free admission. 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 5-21 (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.  Santa Day in the Studio is December 21. Advanced purchase of timed tickets required.

Lenox Holiday Market
December 6, 2025
Join us 12:00 – 4:00 pm. Enjoy complimentary cocktails and gourmet bits. A special gift at every stop with purchase. See the website for a list of participating restaurants.

Breakfast with Santa at Ioka Valley Farm
December 6-7, 2025
Have breakfast with Santa, 8:00 am – 12:00 noon, at Ioka Valley Farm.

Stockbridge Main Street at Christmas
December 6-7, 2025
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.

Christmas at Trinity Concert
December 7, 2025 at 3:00 pm
The Cantilena Chamber Choir will present its 22nd annual “Christmas at Trinity” concert on Sunday, December 7, 2025, at 3:00 PM at Trinity Episcopal Church in Lenox. This beloved holiday tradition combines centuries-spanning choral masterworks with contemporary compositions and special guest readings.

Festival of Trees – Cheshire
December 7, 2025
The Festival of Trees opens to the public Dec. 7 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.

Winter Tea Fundraisers at Arrowhead
December 7 and December 14, 2025
Enjoy a tasty holiday tea in the historic parlors at Arrowhead, with special talks.  See the link for details.

Visit Santa at Greylock Federal Credit Union
December 13, 2025 from 10 am – noon
Santa’s sleigh will jingle into the Berkshires this holiday season, sliding into the Kellogg Street branch of Greylock Federal. The credit union is thrilled to host this esteemed guest and invites all children and their families to pop in for a free picture with Mr. Claus.

Holiday Shop, Sip & Stroll
December 13, 2025 at 3:00 pm
The Southern Berkshire Chamber’s annual Holiday Shop, Sip & Stroll returns to downtown Great Barrington on Saturday, December 13. Join in all the free fun, food and activities for the whole family, enter to win prizes, and make a dent in your holiday shopping list!

Mickey’s Christmas Carol (1983)
December 13, 2025 at 4 pm
Animated family favorite Mickey’s Christmas Carol will play on loop for free at the Mahaiwe’s new Indigo Room during Great Barrington’s Holiday Shop, Sip, and Stroll.

Community Chanukah Celebration at NightWood 2025
December 14, 2025 from 5-7 pm
Stroll through an ethereal winter landscape and immerse yourself in sound, light, and color at NightWood 2025. Afterward, join us at 6:30 pm at the Mansion Forecourt as we kindle the menorah lights and celebrate with live music, Chanukah songs, holiday treat and heaters to keep you warm!

Menorah Lighting
December 15, 2025 at 5:45 pm
Rabbi Rachel Barenblat and Rabbi Seth Wax will lead us in this very special outdoor service at The Williams Inn, sponsored by the Williamstown Chamber of Commerce. People of all ages, faiths, and backgrounds are invited to attend.

Christmas Traditions of the Victorian & Gilded Age
December 20 at 3:30 pm
Local Berkshire County resident and Ventfort Hall volunteer will speak at Ventfort Hall about Christmas traditions in the Victorian and Gilded Age. A tea will follow her presentation.

Mistletoe & Michief at Ventfort Hall
December 21, 2025 at 3:30 pm
Join us for songs of the season with Sherri James Buxton and Bob Shepherd in the beautifully decorated Ventfort Hall. A lovely dessert tea shall follow the concert. Tickets include access to Ventort Hall on the day of the event.

Berkshire Back Society: Back at New Year’s
December 31, 2025 at 6:00 pm
The ⁩⁦Six⁩ ‘⁦Brandenburg⁩’ ⁦Concertos⁩.

New Year’s Eve Ball Drop for Kids of All Ages
December 31, 2025 from 8-9 pm
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.