Celebrate the Season
We hope you enjoy our rundown of holiday events in the region. Just click on the titles and you will link directly to each event site for further information. This is a glorious time to live (or visit) where we do! All of us at BerkshireStyle wish you a season filled with peace, joy and, above all, love.
WEEK OF NOVEMBER 23 2025
MESSIAH SING
Saturday, November 29 at 4 PM
Berkshire Bach invites all singers and lovers of Baroque choral music to raise their voices in popular choruses accompanied by The Berkshire Bach Players. Bring your own score, buy or borrow one of theirs, and kick off the holiday season with this magical musical tradition.
The First Congregational | Church 251 Main Street Great Barrington MA | 413.528.9277
SALISBURY HANDMADE
Saturdays, November 29th and December 13th 10AM-5PM
Featuring different artisans at each market.
White Hart Inn | 15 Under Mountain Rd, Salisbury, CT | 860.435.0030
WEEK OF NOVEMBER 30 2025
CHRISTMAS TOWN FESTIVAL
Friday December 5th, from 5-9:30PM; Saturday December 6th from 9:30AM-4PM.
Celebrate the holiday in Bethlehem, the town dubbed “The Christmas Town" for its annual Christmas Town Festival featuring buildings and churches decorated and brimming with holiday crafters and delicious food.
On the Green | Bethlehem. CT 06751 | 203.266.7510 Extension 400
BERKSHIRE BOTANICAL GARDEN HOLIDAY MARKETPLACE
Friday-Sunday December 5th through 7th, 10 AM-4 PM
An eagerly awaited tradition continues at Berkshire Botanical Garden on Friday, Saturday and Sunday, with a Holiday Marketplace featuring the legendary Gallery of Wreaths. The festivities begin Friday evening with the Holiday Wreath Preview Party from 5 to 7 p.m.
5 West Stockbridge Road | Stockbridge MA | 413.320.4794 for reservations
HOLIDAY MARKET
Saturday December 5th through Sunday December 6th, 10AM-4PM
Noble Horizon will hold its festive holiday market offering a wide variety of locally crafted gifts, artisanal goods and holiday decorations.
17 Cobble Road | Salisbury CT | 860.435.9851
WILLIAMSTOWN HOLIDAY WALK
Saturday December 6th 8AM-6PM
Join in the annual Holiday Walk in Williamstown. The street will be filled with holiday sounds and spirit featuring festivities with traditional New England flair. Check out the fun scheduled for Saturday and Sunday too.
Town of Williamstown MA | 413.458.9077
HUDSON HALL WINTER WALK
Saturday December 6th 5-8PM
The Winter Walk features a bevy of outdoor attractions that can be safely enjoyed by people of all ages and abilities, including locally grown music, art, dance and family fun.
327 Warren Street | Hudson NY 12534 | 518.822.1438
STOCKBRIDGE MAIN STREET AT CHRISTMAS
Friday December 6th and Sunday December 7th
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.
Town of Stockbridge | 413.298.5200 | StockbridgeChamber.org.
HOLIDAY WREATH WORKSHOPS
Saturday, December 6th and Sunday, December 7th, 9-Noon; 1-4PM
Two sessions of wreath-making at the Great Mountain Forest office barn. Advanced registration
Great Mountain Forest | 200 Canaan Mountain Road | Falls Village CT | 860.824.8188
WEEK OF DECEMBER 7TH 2025
VIVACE CHAMBER ORCHESTRA
Saturday December 7th 5PM
Close Encounters with Music will present the Vivace Chamber Orchestra play works by Mozart, Mendelssohn, Britten and Bruch.
The Mahaiwe 14 Castle Street | Great Barrington MA 01230 | 413.528.0100
AN ARROWHEAD CHRISTMAS
December 7th and 14th at 2 PM
Arrowhead, former home of author Herman Melville, will celebrate the season winter season with cozy traditional teas with readings by local authors Michelle Young and Kevin O’Hara. Capacity is extremely limited and pre-registration is required.
780 Holmes Road | Pittsfield MA | 413.442.1793 | melville@berkshirehistory.org
ST ANDREW’S MESSIAH SING-IN
December 12th 8PM
St. Andrew’s Music in the Nave series presents its annual performance of Handel’s Messiah, with Orchestra New England’s James Sinclair conducting the Sherman Chamber Ensemble and guest soloists. Audience members are invited to sing the choral parts and will be provided scores.
St. Andrew’s Parish | 1 Main Street Kent, CT | 860.927.3486
HOLIDAY SHOP, SIP & STROLL
Saturday, December 13th, 3-8:00 PM,
Downtown Great Barrington will have lots of holiday and family-friendly fun in activities throughout town.
Town of Great Barrington MA | 413.528.4284
NUTMEG’S NUTCRACKER
Saturday, December 13th, 12:30 and 4:30PM; Sunday, December 14th, 12:30PM
Enjoy the richness and joy of the Christmas Season with The Nutcracker as performed by the Nutmeg Conservatory.
Warner Theatre | 68 Main Street Torrington CT | 860.489.7180
CHATHAM WINTERFEST
Saturday, December 13th 12PM-5PM
The fun includes a cookie contest, dance demonstrations, strolling carolers, Santa Claus, hay wagon rides and more!
Town of Chatham NY | 518.392.2843
WEEK OF DECEMBER 14TH 2025
IT’S A WONDERFUL LIFE
Sunday December 19th 7PM
The Mahaiwe continues its tradition of presenting a free screening of the holiday classic It’s a Wonderful Life.
Mahaiwe | 14 Castle Street Great Barrington MA | 413.528.0100
WEEK OF DECEMBER 28 2025
BACH AT NEW YEAR: A BAROQUE CONCERTO SHOWCASE
December 31st 6PM
Eugene Drucker, director, leads the Berkshire Bach Ensemble in the six The Brandenburg Concerti.
Mahaiwe | 14 Castle Street Great Barrington MA| 413.528.0100
ONGOING EVENTS
BERKSHIRE MUSEUM: FESTIVAL OF TREES
November 21st-December 28th
Berkshire Museum’s popular winter exhibition comes to the historic grounds at Hancock Shaker Village in Pittsfield, Massachusetts, with Festival of Trees: Barn To Be Wild!
Hancock Shaker Village | 1843 West Housatonic Street, Pittsfield, Massachusetts | hancockshakervillage.org
WINTERLIGHTS AT NAUMKEAG
November 28th through January 3rd. Wednesday through Sunday
A magical outdoor experience as Naumkeag sparkles with thousands of shimmering and artfully designed holiday lights. Bring the whole family for a fun and safe outdoor experience.
Naumkeag | 5 Prospect Hill Road Stockbridge MA | winterlights@thetrustees.org
HOOSAC VALLEY TRAIN RIDES
Berkshire Scenic Railway Museum
Saturdays and Sundays, beginning November 29th, 30th, December 6th, 13th, and 14th Saturdays, 1, 3:30 and 6PM; 11:30AM, 2:00PM.
The Tinsel Liner, a Christmas-themed event, seeks to capture a moment in time and a sense of nostalgia by evoking a 1955 Christmas. Mrs. Claus Express, one day only, 1 and 3 PM, December 20th
98 Crowley Avenue |North Adams MA. 01240 | 413.637.2210
A CHRISTMAS CAROL
December 4th - December 21st
Celebrate this timeless holiday tradition with the whole family, and 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.
Unicorn Theatre | 6 East Street Stockbridge MA 01262 | 413.997.4444
FAMILY FUN IN THE SEASON OF LIGHT
December 22- 23 and 26-29 10AM-3PM
Celebrate the season with family friendly activities during winter break. Join a guided tour to explore the Illustrators of Light exhibit.
Norman Rockwell Museum | 9 Route 183 Stockbridge MA | 413.298.4100
