Happy Holidays in the Berkshires

‘Tis the season for merry making!

The Berkshires is chock full of 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.

NightWood at The Mount

November 17 – January 6, 2024
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 at Berkshire Museum

Through January 7, 2024
Festival of Trees: Nostalgia is on display in Berkshire Museum’s second floor through January 7, 2024.

Norman Rockwell: Winter Wonderland

November 4 – February 25, 2024
On view November 4 through February 25, 2024. Among Norman Rockwell’s best-known illustrations are heartwarming scenes that capture the essence of American holiday traditions celebrated throughout the year – from Valentine’s Day and Independence Day to Halloween, Thanksgiving, and the magic of the Christmas season.

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 24 – January 6, 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.

Lenox Annual Tree Lighting

December 1, 2023
On December 1st, the Lenox Community Center will host the Annual Tree Lighting with special guest – Santa! Follow the above link for other events, too.

Holiday Craft Fair at Simon’s Rock

December 1, 2023
Support local craftspeople and stock up on gifts for the holidays on the Simon’s Rock Campus! December 1, 2-6PM at the Daniel Arts Center.

Stockbridge Main Street at Christmas

December 1-3, 2023
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

December 1-3, 2023
Downtown Pittsfield, Inc. (DPI) will host the Downtown Festive Frolic on Friday, Saturday and Sunday, December 1, 2 and 3. Activities will include the Park Square Tree Lighting Ceremony, The Grinch at Otto’s, free admission to the Festival of Trees, the Holiday First Fridays Artswalk, Pictures with Santa, a Free Kids’ Paint & Sip, a Festive Frolic LEGO® Drop-in, and a Festive Frolic Holiday Market featuring a Krampus Beer Garden.

Lenox Christmas Tree Lighting

December 1, 2023
Lenox Community Center is hosting the Lenox Christmas Tree lighting ceremony, featuring a performance by the LCC Chorus, Dec. 1 at 5:45 p.m. in Lilac Park. Take pictures with special guest: Santa Claus!

Pittsfield Christmas Tree Lighting

December 1, 2023
A chorus will sing holiday carols, and Santa and Mrs. Claus will make a special appearance after the tree is lit, Dec. 1 at 6 p.m.

Williamstown 40th Annual Holiday Walk

December 1, 2023
Williamstown kicks off the 40th Annual Holiday Walk on Friday, Dec. 1, with fun family events happening all weekend long. A Christmas Tree Lighting and caroling will take place on The Williams Inn lawn at 5 p.m., Saturday, Dec. 2.

Stockbridge Main Street at Christmas Holiday Concert featuring The Berkshire Bach Players 2023

December 2, 2023
Celebrate the magic of the season with a joyful holiday musical program located at the First Congregational Church Stockbridge.

Breakfast with Santa

December 2 & 3, 2023
Have breakfast with Santa, 8am to 12pm noon, at Ioka Valley Farm.

Festival of Trees

December 3, 2023
The Festival of Trees opens to the public Dec. 3 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.

Sheffield Christmas Tree Lighting

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

Berkshire Botanical Garden Holiday Marketplace

December 8-10, 2023
An eagerly awaited tradition continues at Berkshire Botanical Garden on Friday evening, Saturday and Sunday, Dec. 8-10, 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.

Holiday-inspired Events at Ventfort Hall

Various
Ventfort Hall, an imposing Jacobean Revival-style mansion built in 1893, has many holiday offerings including a theatrical performance of A Christmas Carol, ghost tours, and Holiday Cabaret “Swingin’ in the Season.”

Joyful Family Holidays

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

Fun Events at Dare Bottle Shop

Various
Check out the latest events focused on food, drinks, and fun – such as Oyster Party Pop-up, Cassis Free Tasting, Shire Donuts Pop-up, and Holiday Tasting Series – at this lovely shop in Lenox.