Holiday Events

Thankful 5k

Registered runners are asked to bring a non-perishable food item(s) to the start of the race. Berkshire Running Center will also be collecting food anytime in the month of November. If you are not running or walking and would like to support local food pantries, please consider purchasing a Thankful Beanie (winter hat) for $25

Non perishable food items will be collected at BRC up until race day.

All participants get extra savings with your hat during Small Business Saturday in Pittsfield!

November 24. Learn more here.

Twas the Night Book Talk

Celebrate the bicentennial of the beloved American poem with the release of a new book.

Meet Pamela McColl, the writer of new book Twas the Night: The Art and History of the Classic Christmas Poem, during the Berkshire Museum’s Winter Fest. Join us as Pamela reads aloud Clement Moore’s “Twas the Night Before Christmas” along with a passage from her book, participates in a Q&A, and signs copies of the book.

November 27. Learn more here.

Hancock Holiday Nights

Our beloved Shaker village sparkles in this multi-sensory experience. Immerse yourself in wonder as our historic buildings are illuminated with artist Joe Wheaton’s spirited light projections. Enjoy a winter stroll through the 19th-century village festively dressed. Journey to the iconic Round Stone Barn to see farm animals like those that might have been present at the first Nativity. Gather for holiday cocktails by the fire. Let time slow and your spirits rise in our new Berkshire tradition.

December 1-31. Learn more here.

Tree Lighting Ceremony

The Taconic High School Chorus will perform a variety of carols around 5:45 p.m. before the ceremony begins, Berkshire Hills Chorus will perform more carols once the tree has been lit, and Santa & Mrs. Claus will arrive following the tree lighting. Those planning to attend the ceremony are asked to bring non-perishable food items that will be donated to the Christian Center’s food pantry.

Otto’s Kitchen & Comfort, 95 East Street, will host a free Hot Chocolate Bar with all the fixins and a Photo Booth.

December 2. Learn more here.

Wreath Auction

Dozens of local artists and members of the Springside Greenhouse Group have donated their talent, time, and materials to create one-of-a-kind, original holiday wreaths, centerpieces, kissing balls, and more. 100% of the proceeds from the sale of these original works of art will be donated to the South Congregational Church’s food pantry.

December 2. Learn more here.

Holiday Artswalk

Save the date and stay tuned for the Holiday Artswalk this December.

December 2. Learn more here.

Kiddo Craft Making Fun

Lee Bank will have free hot chocolate and drop-in ornament making.

Berkshire Art Center (BAC) for a Free Family Drop-In Holiday self-guided art activity.

Witch Slapped, will have a free kids' ornament making and a Drag Storytime as Island Fawn reads a children's holiday story. Free Blue Q gift with purchases! 

The Berkshire Athenaeum, will host a free winter-themed drop-in craft in the Children’s Library.

December 2 & 3. Learn more here.

Elf Invasion Pub Crawl

Locations include Patrick’s Pub, Flat Burger Society101 Restaurant & BarThistle & Mirth, and Methuselah Bar & Lounge. Crawlers should purchase a “Elf ID” ticket in advance which will give them a “tasting” of a specific Berkshire Mountain Distillers’ product at each location, plus some fun elf accessories. Specialty beverages using the highlighted Berkshire Mountain Distillers' product and small plate offerings will be available for purchase at each location.

December 2. Learn more here.

Santa is Here

Come meet Santa and take a free photo with him at the Beacon Cinema!

If you are able, Downtown Pittsfield, Inc. asks that you bring a new pair of socks to donate in exchange for the photo. .

December 3. Learn more here.

Holiday Kids’ Paint & Sip

This free event is best suited for ages 5 to 12, although older children are welcome. All materials, instruction, snacks, and juice will be provided. Children are welcome to drop in anytime over the course of the event. All children must be accompanied by an adult.

December 3. Learn more here.


Visit with an underwater scuba diving Santa Claus, and participate in kayaking, canoeing, and underwater Christmas Tree decorating. Out of the pool, there will also be cookie and wreath decorating and refreshments.

December 3. Learn more here.

The Wizards of Winter

This holiday season, The Wizards of Winter will bring their musical intensity, stage theatrics and holiday fun to The Colonial Theatre. Join The Wizards of Winter as they embark on a musical journey in search of the true meaning of holidays performing their rock opera.

December 3. Learn more here.

Carols of the Bells

Celebrate the holiday season with the First Congregational Church of Lee Handbell Choir, performing festive music around the Museum’s 15-foot Christmas tree in the Santa Classics exhibition.

December 4. Learn more here.

Meditation for a Calm December

Find wellness and peace during the stressful holiday season through meditation. Join Dr. Andrew Vidich to learn a simple yet powerful technique to enrich your life on many levels. There will be a short meditation sitting.

December 6. Learn more here.

Beer and Carols

Come sing along with friends and strangers as we warm up the night with holiday cheer. With beer from Hot Plate Brewing and Zion's own Amy Renak on the piano, you're sure to laugh and make merry! A freewill offering will benefit the Common Room's ongoing efforts to be a welcoming, accessible, and affordable venue for nonprofits, performing arts groups, and community organizations that enrich the Berkshires.

December 8. Learn more here.

Christmas Concert

Traditional and contemporary a cappella carols by Anton Bruckner, Kenneth Leighton, Alice Parker, John Rutter, Anson Olds, and Bob Chilcott will take advantage of the splendid acoustics of this large gothic church. The 70 voice Berkshire Lyric most recently sang a program of Brahms and Mozart at Seiji Ozawa Hall Tanglewood. They will be joined by Lyric’s young women’s ensemble Melodious Accord and by soloists Lily Lothrop, Madeleine Redpath, Rich Geiler and John Demler. All is under the direction of artistic director and conductor Jack Brown and assisted by Joe Rose at the pipe organ.​

December 9. Learn more here.

Natural Holiday Door Swag Workshop

Join farmer and educator Lauren Piotrowski as we use sustainably gathered local materials to create a traditional holiday door swag. In this beginner level workshop we will draw inspiration from the winter landscape and learn the skills needed to make unique and beautiful decorations to grace your home and give as gifts. All materials provided. 

December 10. Learn more here.

The Doo Wop Project Holiday Show

Charl Brown returns to the Colonial with The Doo Wop Project featuring stars from Broadway hits Jersey BoysMotown: The Musical and A Bronx Tale.

This holiday season, The Doo Wop Project will get you into the Spirit! Hear old school holiday classics like The Drifters’ “White Christmas,” The Temptations’ “Rudolph the Red Nosed Reindeer” and Frankie Valli and The Four Seasons’ “Santa Claus is Coming to Town.” The audience will also love contemporary hits like “This Christmas” and “Last Christmas” with a doo wop twist.

December 11. Learn more here.

A Christmas Journey - Yuletide Readings

Please join us for an unforgettable evening as noted Pittsfield author Kevin O’Hara shares joyous and heartfelt tales of his Pittsfield childhood. Kevin will read a selection of his own Christmas tales from his illustrated book,  A Christmas Journey.

December 14Learn more here.

Come Home for The Holidays: A Colonial Family Concert

Berkshire Theatre Group invites you back home to The Colonial Theatre with a very special concert for the whole family. There is no better way to celebrate the spirit of the holidays than with the Berkshire tradition of story and song. Enjoy performances by some of the area’s best known and respected artists from the diverse Berkshire County music community along with our very own BTG Youth Chorus. 

December 18. Learn more here.

The Art of Hanukkah

Nancy Kotz will explore an overview of artworks related to the miracle of the oil and the re-dedication of the Holy Temple. It is both the ‘Holiday of Freedom’ and the ‘Holiday of Lights.’ Illuminated manuscripts, etchings, woodcuts, photographs, paintings, and Hanukkah Lamps of marble, brass, silver, stone, iron, and glass are all included. The Art of Hanukkah tells the story of this holiday through art objects from many centuries.

December 18. Learn more here.

Holiday Lights

A virtual program that offers a tour of Arrowhead decorated for the holidays, seasonal readings, 19th century holiday recipes, and a peek at some objects from our collection that are not often on view. Lizzie Melville, as portrayed by actress and Arrowhead docent Francine Ciccarelli will also be on hand to welcome you to her home.

December 21. Learn more here.

Holiday Lights

Habari Gani! The Women of Color Giving Circle cordially invite you to celebrate Kwanzaa. Stay tuned for more details on their Facebook page.

December 29. Learn more here.

Santa Classics Exhibition

Philadelphia-based artist Ed Wheeler places Kris Kringle into your favorite classical works of art!

This exhibition features a selection of 31 works from Ed’s catalog along with the Museum’s 15-foot tall, decorated tree in the center of the Ellen Crane Memorial Room.

Now - January 8. Learn more here.

Shop Local This Season

Small Business Saturday - Passport to Downtown

To highlight our local businesses, shoppers are invited to shop our bustling district on and by doing so, have the chance to win a Downtown Pittsfield Prize Package! Pick up your Passport to Downtown Pittsfield at participating businesses on Saturday, November 26. Collect one stamp from every business where you make a purchase, and the more stamps you collect, the greater your chance to win the Downtown Pittsfield Prize Package.

November 26. Learn more here.

Shop & Sip 

Do mimosas make shopping better? We say yes. Skip the long lines on Black Friday and relax with a free mimosa at our all-day Shop & Sip. Choose the perfect gift from a selection of jewelry made by local artisans, handcrafted oval boxes, honey and jam, cookbooks, Christmas ornaments, toys, and more.

November 27. Learn more here.

Give the Gift of Local Art

The Artists at the historic Clock Tower will host a Holiday Open Studios weekend inviting you to come check out their newly created, original small paintings and printed items perfect for gift giving.

December 2 - 4. Learn more here.

Holiday Shindy

The 15th Annual Holiday Shindy is brimming with the best in local artisans and magically festive destination shopping.

For thirteen years the Holiday Shindy has been a magical shopping tradition, showcasing artisan vendors from across the region. The Shindy features the chance to meet and watch local farms and makers weave, sew, preserve, and whittle.

Vendors are listed on the website.

December 10. Learn more here.

Mingle & Jingle

Downtown Pittsfield is the destination for last-minute holiday shopping. Shop local businesses downtown for great holiday gifts; and visit an indoor Holiday Shop + Sip Pop Up Market featuring holiday gifts from local makers, crafters, and artisans organized by CozQuest, and featuring specialty drinks from Berkshire Mountain Distillers!

Times and locations and more information will be announced soon.

December 17. Learn more here.

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