Holidays in the Berkshires

Holiday Happenings in the Berkshires

With twinkling lights aglow, the sweet smell of cider, and winter’s first flakes floating through the chilled air, the festive season is a merry time of year in the Berkshires. Whether you’re planning a relaxing winter escape for two or looking for holiday delights that the entire family will cheer for, the below line-up of merry happenings are sure to warm the hearts of even the grumpiest Grinch.

Lenox Winterland Holiday Tree Walk

Lenox | Month of December
Starting December 1, stroll through Lenox for the Holiday Tree Walk. Admire 15 white, 6-foot trees on display along Main Street, all decorated by local businesses and artists. Plus view smaller green trees in front of businesses downtown.

Holiday Stream of STREB Extreme Action Company’s 2021 Dance Festival

Jacob’s Pillow | December 1, 2021 – January 6, 2022
A special edition of the STREB Extreme Action Company’s 2021 Jacob’s Pillow Dance Festival performance, featuring a unique retrospective of Elizabeth Streb’s work from the 70s and 80s alongside bonus behind-the-scenes content and archival footage, will be available as part of a Holiday Stream offered through the Pillow this holiday season. Tickets are on sale as of Nov. 15 and cost $15. The performance will feature nearly 50 minutes of STREB Extreme Action Company’s performance on the outdoor stage at Jacob’s Pillow this summer, which marked the company’s first return in over 20 years. The works feature STREB’s signature style that combines bravery and sheer athleticism.

Hancock Holiday Nights

Hancock Shaker Village | 15 nights in December
This December, the oldest Shaker Village in New England will sparkle in a new multi-sensory month-long experience called Hancock Holiday Nights. Enjoy five stunning art light projections that immerse you in wonder. Stroll through the 19th-century village transformed with festive decorations. Say goodnight to donkeys, sheep, and other animals. Preview never-before-seen Shaker miniatures. Gather for holiday cocktails by the fire. Let time slow and your spirits rise during 15 wonderfilled nights in December.

Wreath Decorating

Whitney’s Farm Market & Garden Center | December 2 & 9, 2021
Come enjoy an evening out at the farm with your friends and family! The event includes at 12″ wreath, a bow and all sorts of ornaments to make it your own. There will be festive display of wines as well as light refreshments made by our bakery and deli! The cost of the event is $80 per person, tickets can be purchased in the store. We will be requiring everyone to wear a mask regardless of vaccination status. Space is limited, so get your ticket before they sell out!

Irving Berlin’s White Christmas The Musical

Berkshire Theatre Group | December 2 – 23, 2022
Irving Berlin’s White Christmas is a timeless tale of joy and goodwill about a song-and-dance team putting on a show in a magical Vermont inn and falling for a stunning sister act in the process. Full of dancing, laughter, and some of the greatest songs ever written, the dazzling score features “Blue Skies,” “I Love a Piano,” “How Deep is the Ocean?” and of course the unforgettable title track, “White Christmas.” Give everyone the gift they’re dreaming of with this merry and bright holiday musical at the Colonial Theatre.

Berkshire Botanical Garden Holiday Marketplace

Berkshire Botanical Garden | December 3 – 6, 2021
100 unique, one-of-a-kind designer wreaths as well as an assortment of holiday-blooming plants including amaryllis and paperwhites in decorative and clay containers, succulent arrangements and holiday gift items.

Holiday Winter Market!

85 Main St, North Adams | December 4, 2021 at 9AM
December 4th Holiday Winter Market with Bohemian Nouveaux Bakery !! come get Traditional Sour Cream Christmas Cookies, Hand Painted Christmas Cookies, Chocolate Rugelach Rolls, Challah Bread , Gingerbread Cake, Men & Mini Houses and So Much More! All made with Organic & Local eggs, butter etc!! and we may still be making Pies!! Come see us at the North Adams Winter Farmers Market #85 Main St. North Adams MA from 9am -1pm

One Man Play – “A Christmas Carol”

Ventfort Hall Mansion and Gilded Age Museum | Saturday, December 4, 2021 at 3PM
The great-great-grandson of the literary legend Charles Dickens, British actor Gerald Charles Dickens returns to Ventfort Hall to present a one-man theatrical performance of his ancestor’s classic work A Christmas Carol at Ventfort Hall Mansion and Gilded Age Museum on Saturday, December 4, and Sunday, December 5, 2021 at 3:00 pm. An elegant tea will follow. Using his own adaptation of Charles Dickens’ classic Christmas tale, Gerald plays 26 characters using his vocal and physical talents to bring each scene vividly to life. In 1993, he created as his first one-man show, A Christmas Carol, inspired by Charles’ own energetic readings of the 1860s in the United States and elsewhere. Tickets for A Christmas Carol and the tea are $60. Ventfort Hall will be in full Christmas Regalia! Reservations are required and can be made by calling (413) 637-3206. Please note that all tickets are nonrefundable and non-exchangeable. Payment is required to make a reservation for an event. Proof of vaccination, ID and masks are required.

Joyful Holidays Family Day

Norman Rockwell Museum | December 5, 2021 at 11AM
Children’s Book Readings from Jan Brett: Stories Near and Far, on the hour. Throughout the day: Winter Wonderland Scavenger Hunts (for children & families); Drawing in the Galleries – Join chief curator Stephanie Habboush Plunkett and the Museum staff for an interactive gallery drawing experience that will inspire a closer look at the art on view.
Meet Hedgie! Meet and take a pic with the beloved iconic character from Jan Brett’s books. (Costumed character; not a real hedgehog!); Jan Brett-signed books available in the Museum Store. Included with admission; free for kids & teens, and Members.

Stockbridge Main Street at Christmas

Stockbridge | December 4 & 5, 2021
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.

Create ‘n Sip @ Zucchini’s

Zucchinis Restaurant | December 6, 2021 at 6PM
Stop and create for a bit! Grab your friends and plan for a night out. These will make a great gift for yourself or for any host! These centerpieces are made with hearty cedar, boxwood, balsam and will have hints of special winter stems and petals. These greens will fragrantly fill your home with the smell of winter, and last long past the holidays with proper care. Your choice of candle color (white, red, gold) and accent colors (red, green, silver, gold or plaid). $75 per person. Sign up at

Jane Lynch & Kate Flannery – A Swingin’ Little Christmas

Mahaiwe Performing Arts Center | December 10, 2021 at 8PM
Jane Lynch is an actress, singer, playwright, and author. She is currently the two-time Emmy Award-winning host of NBC’s Hollywood Game Night and can be seen on Amazon Prime’s The Marvelous Mrs. Maisel. In 2015, Jane embarked on her own live concert tour, See Jane Sing with Kate Flannery, Tim Davis and The Tony Guerrero Quintet. Their holiday album, A Swingin’ Little Christmas hit Billboard’s Top 10 Adult Contemporary chart. In 2018, Jane and Kate premiered their new cabaret show, Two Lost Souls at NYC’s legendary venue, The Carlyle

Williams College Wind Ensemble

Williams College Department of Music, Chapin Hall | Friday, December 10, 2021 at 7:30PM
Williams College Wind Ensemble returns to the Chapin Hall stage with a program titled, Scenes of Song and Dance. Conducted by Brett Wery, the ensemble presents works by Samuel Barber, William Schuman, Warren Benson, Norman Dello Joio, and Valerie Coleman.

Ginger Bread House Decorating

Red Lion Inn | Saturday, December 11, 2021 at 11AM – 3PM
Grab your spot and get in the spirit! Decorate your own gingerbread house with The Red Lion inn Pastry Chef, Kate Fitzmaurice. Selection of candy and decorations will be provided. Limited seats available $35/ticket. Ticket admits 1 child, 2 adults. 1 House/child. For reservations call the front desk at (413) 298-5545. This event is part of Joyful Family Holidays, a month-long celebration of holiday cheer and happenings throughout December presented by The Red Lion Inn and Norman Rockwell Museum. For the full schedule of events, visit:


Greylock Works | Saturday, December 11, 2021
Fifty of the region’s exceptional artisans will be set up for your intimate engagement and first dibs on exquisite locally handcrafted holiday gifts. Gather your friends and toast to the season and the beauty of community with a complimentary glass of champagne cider crafted at Greylock WORKS by the Berkshire Cider Project. Limited First Look tickets available for advance purchase. $25 each


Berkshire Music School | Saturday, December 11, 2021 at 3pm
Featuring intricate three-part harmonies, dance tunes and several instruments, Wintergreen returns to The Taft with a mix of contemporary and traditional music from the British Isles and America, as well as original songs.  This family concert will reflect the variety of ways we celebrate the holiday season, and will include some familiar and unusual songs that mark the rebirth of the year and the end of dark winter. There will be many opportunities for audience participation!  Reservations recommended. 

Jingle Bell Run/B21 Awards

Berkshire Running Center | Saturday, December 11, 2021 at 9AM
The B21 Hoodies are in so that means it’s time to run! Join us for our annual fun and free jingle bell run to raise money for the Eagle Santa Toy Fund. No registration needed, this is a fun run. Participants are asked to donate if they are able for this great cause. The Eagle Santa Fund, which is sponsored by the Berkshire Eagle, strives to raise about $45,000 a year to provide deserving children in Berkshire County with Christmas gifts. This is our ninth year hosting this free and fun event, we hope you join us. Wear your bells and fun outfits and jingle all the way around the Downtown Loop to have fun and help this great cause. Then join us back at BRC for your hoodie award ceremony! Stick around for our best sale of the season and get an additional 10% off your purchase with your B21 hoodie!
For more information email [email protected]

The Wickhams: Christmas At Pemberley

Shakespeare & Company | December 16 – 19, 2021
This holiday season, Shakespeare & Company presents a costumed, staged reading of The Wickhams: Christmas at Pemberley, featuring the many familiar characters of Jane Austen’s Pride and Prejudice, as well as some new faces.

Winter Tours at Arrowhead

Arrowhead | Through December 18
Through December 18, tours of Arrowhead are available on Saturdays only, at 11 am, 12 pm, and 1 pm on a first-come, first-served basis. Tour size is limited to ten; reservations are not accepted.Between December 19–April 1, Arrowhead is available for private guided tours only. Tours must be scheduled at least one week in advance; phone 413 442 1793 or email [email protected].

Holiday Cabaret and Tea – “Swingin’ in the Season”

Ventfort Hall | December 19, 2021
Celebrate the season with a Holiday Cabaret performed by singer Sherri James Buxton with Bob Shepherd accompanying on the beautiful rosewood, six foot Steinway.  The mansion will be beautifully decorated for the holiday season. A lovely tea shall follow. The program will feature seasonal songs from Broadway musicals, the Great American Songbook, traditional favorites and some audience participation.


The Mount, Edith Wharton’s Home | Through December 31, 2022
A sound and light experience that transforms the property into a fantastical winter landscape for the holidays. Inspired by the natural beauty and architecture of The Mount, NightWood will immerse visitors in a series of vignettes designed to evoke elements of fantasy, mystery, and whimsy.

Holiday House Tours at The Mount

The Mount | Through January 2, 2022
The Mount is dressed up for the holidays! While the Whartons did not spend their Christmases at The Mount, we have imagined what it might have looked like. Self-guided house tours featuring festive decorations are available Saturdays and Sundays through January 2 (closed Christmas weekend).

Winterlights at Naumkeag

Naumkeag | Through January 9, 2022
A magical outdoor experience at Naumkeag as it sparkles with thousands of shimmering and artfully designed holiday lights. Bring the whole family for a fun and safe outdoor experience. Tickets are nearly sold out. Book for January today.

Daffodil & Tulip Festival

Naumkeag | Tentative April 21 – May 15, 2022
Stroll through the 8 acres of our world-renowned gardens decorated with over 130,000 daffodils, tulips, and minor bulbs as we celebrate spring in the Berkshires.

Winter Farmers Markets

Berkshire Grown | November 2021- April 2022
The winter markets will feature the abundance of locally grown and produced foods unique to be found in the Berkshires. Vendors offer local products ranging from winter squash, greens, and root crops, to apples, meats, cheeses, honey, and maple syrup, as well as baked goods, jams, ferments, and cider. Admission to the Farmers Markets is free and SNAP is accepted with a 100% match, available at the Market Manager’s table.

Holiday Dining

Haflinger Haus Restaurant, Tavern & Inn

Menu available for takeout, local delivery and curbside pickup.

Mazzeo’s Ristorante

Special holiday menu available for Take Out.

Red Lion Inn

Menus available for Main Dining Room & Tavern locations.

Gift Giving – Keeping it Local

Berkshire Paint & Sip

Purchase a gift certificate for friends or family. Each guest joins the virtual party online from the comfort of their own home. All that’s needed is the DIY Paint Kit provided and the individual’s beverage of choice.

Soma’s Aromas

Soma’s Aromas is a Berkshire based candle maker specializing in 100% soy candles made with quality phthalate-free fragrances infused with therapeutic grade essential oils. Great gift for that special someone!

Ward’s Nursey & Garden Center

Shop online or visit their delightful Christmas Room displays inside the store, filled with seasonal decorations and twinkling trees.

Berkshire Museums

Offers a wide variety of gifts for adults and children alike. Check out the gift shops at Berkshire Museum, Hancock Shaker Village, MASS MoCA, Norman Rockwell Museum, and The Clark. And don’t forget the Eric Carle Museum of Picture Book Art, in nearby Amherst, offering imaginative toys, puzzles, games, and more!