Stockbridge Main Street at Christmas – December 6-7, 2025 -Tickets to the annual event are now on Sale!

Rediscover the joys of the holidays in Stockbridge, MA, where the town transforms into a magical New England village, adorned with twinkling lights and charming holiday wreaths that evoke the spirit of the season. This enchanting destination offers a delightful array of family-friendly activities that promise to create cherished memories for all. From captivating live performances and historic property tours to bustling holiday markets and the mesmerizing Winterlights display, there’s truly something for everyone to enjoy. As the weekend culminates on Sunday, Stockbridge comes alive with a heartwarming reenactment that beautifully embodies the spirit of Norman Rockwell’s iconic holiday scene, “Home for Christmas.” The festivities celebrate Rockwell’s popular depiction of what for many is the quintessential small New England Town, with all the longing for a simpler time that it represents.

STOCKBRIDGE, MA

Berkshire Botanical Garden Holiday Marketplace and Gallery of Wreaths, 5 West Stockbridge Road, Stockbridge, MA (413) 298-3926

Friday, Saturday and Sunday, December 5-7
An eagerly awaited tradition continues at Berkshire Botanical Garden with Holiday Marketplace featuring the legendary Gallery of Wreaths.

The festivities begin Friday evening, December 5, with the Holiday Wreath Preview Party in the Center House from 5 to 7 pm. The party includes early wreath-buying opportunities, live music, hors d’oeuvres, libations, and merriment! For tickets, visit BerkshireBotanical.org

The Holiday Marketplace runs Saturday and Sunday, December 6 & 7 from 10 am to 4 pm. 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. Free Admission.

Berkshire Theatre Group, Box office (413) 997-4444

At the Unicorn Theatre, 6 East Street, Stockbridge, MA

Thursday, December 4 – Sunday, December 21
A Christmas Carol
Celebrate this timeless Berkshire County 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. Journey back to Victorian England and experience the classic story filled with holiday carols and the wonderment of the season.
Production by Charles Dickens adapted by Eric Hill

At the Colonial Theatre, 111 South Street, Pittsfield, MA
Saturday, December 13 at 7:30pm
An Evening of Holiday Jazz with Tim Jones in The Garage at the Colonial Theatre
Celebrate the season with Berkshire Theatre Group at An Evening of Holiday Jazz with Tim Jones, an intimate and spirited concert at The Garage. Join BTG alum Tim Jones and a stellar lineup of the Berkshires’ finest jazz musicians as they bring beloved holiday classics to life in a warm, close-up setting.

Sunday, December 14 at 2pm
Mutts Gone Nuts: Santa Paws
at the Colonial Theatre

Get ready for a tail-wagging, laugh-out-loud holiday treat for the whole family! Mutts Gone Nuts: Santa Paws returns to The Colonial Theatre with more mayhem, more mischief and even more four-legged fun. This festive canine spectacular stars an all-rescue cast of outrageously talented pups in a high-energy show packed with jaw-dropping tricks, belly laughs and heartwarming moments.

Saturday, December 20 at 7:30pm
The Wizards of Winter
at the Colonial Theatre

Celebrate the season with a spectacular holiday rock opera that will leave you filled with wonder and cheer! Returning for their third year at The Colonial Theatre, The Wizards of Winter will light up the stage with The Christmas Dream—a theatrical musical journey that blends the excitement of rock with the heart of the holidays.

For tickets, visit BerkshireTheatreGroup.org

Chesterwood at Christmas, 4 Williamsville Road, Stockbridge, MA (413) 298-3579

Open Friday, Saturday and Sunday in December (closed December 6th for Stockbridge Main Street at Christmas tours)
Visit Chesterwood decorated in style for the holidays!
* Self-Guided Touring in the Residence & Studio
* Complimentary Hot Cider
* Pop-Up Holiday Gift Shop
Family Day with Santa in the Studio:
Sunday, December 21, 11:00-4:00pm

Naumkeag Winterlights, 5 Prospect Hill Road, Stockbridge, MA

Friday, November 28, 2025 – Saturday, January 3, 2026 Every Wednesday – Sunday
This holiday season the beautiful garden property sparkles with thousands of shimmering, artfully designed holiday lights. Bring the whole family for a magical, fun, outdoor experience – with food, refreshments, and more.

Rockwell Holidays at Norman Rockwell Museum, 9 Glendale Rd/Rte 183, Stockbridge, MA (413) 298-4100

See Rockwell’s original panorama painting of Main Street Stockbridge at Christmas, among other iconic holiday paintings, plus special exhibitions including Jazz Age Illustration, Norman Rockwell and the Illustrators of Light, The Art & Life of Deb Koffman, and more. The annual display of the miniature Village of Stockbridge and train set; plus tours of Norman Rockwell’s art and holiday favorites complete your Rockwellian experience in Stockbridge. Events throughout December welcome all ages for a memorable visit, including family artmaking, Saturday Jazz music, gallery tours, and December Vacation programs; see more at NRM.org/events. For tickets visit NRM.org

Home for the Holidays, the Museum’s annual exhibition exploring Norman Rockwell’s most iconic holiday imagery—on view now through February 22, 2026.

Saturday, December 6,10:30am – 3:30pm
Special Main Street at Christmas program
Norman Rockwell’s Stockbridge Walking Tour
Take a guided walking tour of downtown Stockbridge and discover how the town and its inhabitants both inspired Norman Rockwell and appeared in some of his most iconic works of art. Explore the history of this 1734 village–including its Mohican origins. Stops will include Norman Rockwell’s home on South Street, his first studio on Main Street, the Old Corner House (site of the original Norman Rockwell Museum), Chief John Konkapot’s property, the Red Lion Inn, the former site of Alice’s Restaurant, and more!

Joyful Family Holidays at the historic Red Lion Inn, a Main Street landmark for hospitality for over 250 years, (413) 298-5545

All December long, The Red Lion Inn comes alive with festive pop-ups, events, and special programming to celebrate the season.

The Women’s Service League of the First Congregational Church Holly Fair, 4 Main Street, Stockbridge, MA (413) 298-3137

Saturday, December 6 from 10:00am-1:00pm
Sponsored by the Women’s Service League, the Fair features hand-made crafts, gifts and decorations, holiday greens, baked goods, Tea Room, Grandma’s Attic, Santa Claus, silent auction cross-stitch, and more. All proceeds to charity. Free Admission.

Stockbridge Library, Museum & Archives, 46 Main Street, Stockbridge, MA (413) 298-5501

Friday, December 5, 5:00-5:30pm and Saturday December 6, 2:00-2:30pm & 3:00-3:30pm
Olga Dunn Dance Company performance “The Nutcracker Seedling” Three Performances, All first-come, first served basis

Saturday, December 6, 10:00am-2:00pm
Winter Family Fun Day and Nutcracker Collection Display All day long they will have a craft table available where children can decorate a snowflake, indoor winter games and a scavenger hunt, and an outdoor StoryWalk© and decorated gardens that you can walk through. At 10:45 a.m. there will be a winter-themed story time with the youth librarian.

ADAMS, MA

Hoosac Berkshire Valley Train Experiences

December 20, 1:30 or 3:00pm
Mrs. Claus Cookie Express, One Day Only

November 29th & 30th, December 6th, 7th & 13th
Tinseliner Scenic Christmas Train
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!

GREAT BARRINGTON, MA

Mahaiwe Performing Arts Center, 14 Castle Street, Great Barrington, MA, (413) 528-0100

Friday, December 5, 5:30pm and 8:30pm
Jazz pianist Isaiah J. Thompson will be performing A Guaraldi Holiday with a quartet at the Mahaiwe’s Indigo Room

Saturday, December 13 at 4:00 pm – 7:00 pm
Mickey’s Christmas Carol (1983). Indigo Room 20 Castle Street, Great Barrington, MA
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.

Friday, December 19 at 7:00 pm
It’s a Wonderful Life (1946)
The Mahaiwe presents a free screening of It’s a Wonderful Life per annual tradition.

Saturday, December 20 at 8:00 pm
John Pizzarelli Trio: Tony Bennett – The Art of Excellence
Grammy Award-winning producer and guitarist extraordinaire, John Pizzarelli salutes the legendary Tony Bennett celebrating over 60 years of unparalleled artistry.

Wednesday, December 31 at 6:00 pm
Berkshire Bach Society presents: Bach at New Year’s – The Six ‘Brandenburg’ Concertos
The Berkshire Bach Society presents Bach at New Year’s: The Six ‘Brandenburg Concertos’, an event that has been a holiday tradition since 1993.

LENOX, MA

The Mount’s NightWood, 2 Plunkett St, Lenox, MA (413) 551-5111

November: 21, 22, 26, 28, 29
December: 6, 12, 13, 18-23, 26-31
January 2026: 2-3
The Mount’s popular immersive sound and light installation, returns on November 21 and runs through January 3, 2026. Visitors wander through a dreamlike landscape where story, sound, and setting merge into pure magic. For tickets visit edithwharton.org

Shakespeare & Company, 70 Kemble Street, Lenox, MA (413) 637-1199

December 12-14 2pm & 7pm
Sense and Sensibility Elayne P. Bernstein Theatre
The popular Winter Show returns this year with Sense and Sensibility: a fast-paced, staged reading that brings the wit and romance of Jane Austen’s classic tale to life.
Sense and Sensibility follows the fortunes, and misfortunes, of the Dashwood sisters — sensible Elinor and hypersensitive Marianne — after their father’s sudden death leaves them financially destitute and socially vulnerable.
Set in late 18th-century England, the play is full of humor, emotional depth, and bold theatricality. Sense and Sensibility examines our reactions, both reasonable and ridiculous, to societal pressures. When reputation is everything, how do you follow your heart?

Ventfort Hall Gilded Age Mansion & Museum, 104 Walker Street, Lenox, MA 413-637-3206

Come and visit and enjoy the lavish holiday decorations throughout the mansion. From late November through early January, the mansion is dressed in its holiday best. Twinkling lights, garlands, and the charm of the season fill every room, creating a festive and cozy atmosphere that’s hard to find anywhere else. Be sure to plan your visit. Come early on with family friends for the perfect holiday picture photo-op!

Ventfort Hall will host a Children’s Evening Story Hour again this year during the holiday season. This enchanting evening will bring families together for a cozy celebration of classic winter stories, hot cocoa, snacks, activities, and a memorable reading experience. Get Cozy. Arrive in your favorite pajamas and bring blankets to snuggle up with in the mansion library. Allergy-friendly food options are welcome if brought from home.

On December 15^th the story hour will feature these cherished books: The Hat by Jan Brett, The Snowy Day by Ezra Jack Keats, and Katy and the Big Snow by Virginia Lee Burton.

On December 29^th the story hour will feature these cherished books: The Snowy Day by Ezra Jack Keats, The Mitten, by Jan Brett, Polar Express, by Chris Van Allsburg, and The Tomten, by Astrid Lingren

Ventfort will also offer Tea&Talks, Ghost Tours and marionette shows, Rapunzel, with puppeteer with Carl Sprague.

WILLIAMSTOWN, MA

Clark Art Institute, 225 South Street, Williamstown, MA (413) 458-2303

December 27, 1-3pm
The Met: Live in HD—The Magic Flute (Encore)
A treasured holiday tradition, Mozart’s heartwarming fairy tale takes the stage in the Met’s abridged, English-language production by Julie Taymor—the Tony Award–winning director of Broadway’s The Lion King. Featuring some of opera’s most popular melodies and brought to life with colorful sets and costumes and dazzling puppetry, it’s perfect for audiences of all ag