15 Holiday Things To Do In The Berkshires!

I love this time of year in The Berkshires.   Here is a list of 15 Holiday Things To Do In The Berkshires.  The first winter I spent in The Berkshires was  a time of exploration.  I had decided that i wanted to buy a country home.  Being the cautious person that i am I rented a beautiful house first in Stockbridge, Ma.  The rental  was for 6 months, hoping that would be long enough for me to see if  The Berkshires was the right spot for me.  The  rental house  was way big for me and my dog Spike,  but i figured i was going to be inviting many friends to visit me in  The Berkshires for weekends and i wanted to have plenty of room for entertaining.  The house was owned by the Boston Symphony Orchestra and used in the Summer months during Tangelwood.   As i look back so many years later,  I believe it was that first snowy Holiday Season, and Winter in Stockbridge, Ma. that made me fall in love with The Berkshires.

Here Are 15 Things To Do during this Holiday Season.

1. 26th Annual Festival of Trees

Each year, the Berkshire Museum spruces up the galleries with scores of festive trees decorated by community organizations, businesses, and school children. This year’s theme is Storybook Forest.

November 13 – January 2

Berkshire Museum



2. Home for the Holidays

Norman Rockwell presents a special holiday installation of original artworks and objects, including greeting card and cover illustrations, which brought the spirit of the holiday’s home.

November 13 – January 16

Norman Rockwell Museum



3. Holiday Farmers Markets

Williams College Field House on Latham Street in Williamstown 10:00 am–2:00pm.

Old railroad station on Castle Street in Great Barrington 9:00 am–1:00pm

Each location will be offering components for holiday meals from farms and artisan producers in the region along with live entertainment.

November 20

Berkshire Grown

Great Barrington


4. Michael Feinstein Holiday Show

A Broadway Classics Crooner!

November 26

8:00 pm.

Mahaiwe Performing Arts Center, Inc.

Great Barrington


5. Home “Made” for the Holidays

Featuring juried artisans from the Berkshires and surrounding towns will be held from 11am – 4pm.  There will be door prizes and Goodie bags will be given to the first 50 (adult)attendees!  A small entrance fee of $2 is charged to offset the cost of advertising.

November 27

Jae’s Spice (2nd floor)


297 North St., Pittsfield

6. The Sound of Christmas ~Elisabeth von Trapp & The Empire Brass

Elisabeth von Trapp, was born and raised in Vermont, Elisabeth is the granddaughter of the legendary Maria and Baron von Trapp, whose story inspired The Sound of Music. The Empire Brass, led by Berkshires’ own Rolf Smedvig, dazzles audiences worldwide with their virtuosity and charisma. Their entertaining holiday program combines the classic and the new; covering holiday standards, classical transcriptions, traditional carols and original Empire Brass arrangements.

November 30

The Colonial Theatre



7. The Santaland Diaries

A warm and festive little one-man tale that has just the right mix of humor, charm, wit and edge to have everyone rollicking in the aisles. Occasionally subversive, alarmingly clever, engagingly poignant and always side-splittingly funny, this true account of Mr. Sedaris’ time spent working as a Christmas elf in Macy’s Department Store is well on its way to becoming a modern holiday classic.

December 2 – 30

Shakespeare & Company



8. Williamstown Holiday Walk Weekend

An annual event for shopping, entertainment and a fun-filled weekend of holiday cheer. The Festivities begin on Friday, December 3rd at 8:00 PM with the Dave Bennett Septet at the Sterling and Francine Clark Art Institute.

On Saturday, December 4 Images Cinema will host the holiday movie “ELF along with Habitat for Humanity’s Christmas Tree Showcase and the Alternative Gift Fair at the First Congregational Church. The New Toy Collection will be held at The American Legion. The Annual Reindog Parade kicks off on Spring Street and don’t miss the holiday sounds of The Williams Handbell Choir or the Holiday parade with the Williams College Marching Band, Williams College Equestrians and a special visit from Santa. Shops will offer a variety of unique holiday gifts, including jewelry, handmade ornaments, and more. The evening caps off with a Tree Lighting on Spring Street.

On Sunday, December 5 the Williamstown Elementary School hosts the annual Pancake Breakfast and Crafts Fair. Families join in for the free Family Skate at the Williams Rink and a special Tree Lighting will take place at Five Corners in South Williamstown.

December 3 -5

Williamstown Chamber of Commerce



9. Holiday Tree Lighting

At Lilac Park with a visit from Santa Claus.

December 3


Lenox Chamber of Commerce


10. Chanukah Puppet Show

The Mystery of Hanukkah Harry
Join Joshua Finkelstein and his best friend Danny as they go on a quest for the identity of the mysterious Hanukkah Harry.  They’ll ask for help from the audience as they try to sort out the clues they get from their family and community.  Their shenanigans will have the whole audience laughing, yet the show also contains an important lesson about the essence of Hanukkah.  As Josh and Danny discover, Hanukkah Harry doesn’t deliver presents; he is alive in anyone who stands up for him or herself and creates a miracle for the people he or she loves.  4:00- 5:30pm. A family show for all ages.

December 4

Hevreh of Southern Berkshire, Inc.,

Great Barrington

11. Lenox Inn Tour

Tour historic inns (Apple Tree Inn, Birchwood Inn, Rookwood Inn, Garden Gables Inn, Kemble Inn, Gateways Inn, Summer White House, Village Inn) on the Lenox Inn Tour each festively decorated for the Holidays. Tickets are $20.00.

December 4

Noon – 5:00pm

Lenox Chamber of Commerce


12. 21st Annual Stockbridge Main Street at Christmas

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, offering a full range of activities, with highlights including a holiday house tours, caroling, and a holiday concert, along with a recreation on Sunday of the scene depicted in Main Street at Christmas, complete with vintage automobiles.

December 4 & 5

Stockbridge Chamber of Commerce


13. A Merry Nutcracker Tea Party

A Merry Nutcracker Tea Party will include traditional as well as new dance themes performed by the dancers from American Dance Institute Ensemble, Albany Berkshire Junior Company, and Academies of Cantarella School of Dance. The ballet will be followed by a Holiday Victorian Tea.

December 5

3:30 pm

Ventfort Hall



14. Holiday Stroll

The Annual Holiday Stroll from 3:00 – 9:00pm in downtown Great Barrington will feature Santa, carolers; vendors; and the town tree lighting. Restaurants and businesses will be open for holiday shopping/dining and will be offering holiday specials.

December 11

Southern Berkshire Chamber of Commerce

Great Barrington

15. Rumpelstiltskin

Puppeteer Carl Sprague will bring to life the classic fairy tale Rumpelstiltskin.   The audience will have the opportunity to meet this wizard, who knows how to pull a few strings, over a Children’s Holiday Tea.

Ventfort Hall




For a more complete list of goings on


Got A Question?

Ask Marlene  413 717-0773

E-mail:  marlene@berkshirecountryhomesrealestate.com

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Marlene Goldstein
Berkshire Country Homes, LLC
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