Guides

Guiding you through the exciting world of events around you and Zeitcaster's Community Calendar Platform

Must-do Holiday Events in the Berkshires

winter-events

The most magical time of the year is almost upon us, and there’s no better place to celebrate the joy of the season than in the picturesque Berkshires.  Whether you’re a local or visiting the Berkshires from out of town, Zeitcaster has you covered for fun holiday festivities. Come cozy up with these top picks!

  1. Festival of Trees – Barn to Be Wild: November 21-December 28, Hancock Shaker Village. Come explore the Village as you gaze upon beautifully decorated trees, each ornamented by a different Berkshires-based organization or business designed around our theme. The theme, Barn to be Wild, celebrates this year’s unique partnership between Berkshire Museum and host site Hancock Shaker Village – the oldest working farm in the Berkshires and home to one of the region’s most iconic round stone barns! 
  2. Winterlights at Naumkeag, November 28-January 3. Behold the magic of thousands of sparkling lights along the garden paths. Bundle up and take keepsake photos by the whimsical displays and then warm up with hot cider. This event is not to be missed!
  3. A Christmas Carol: December 4-21, Unicorn Theater. Allow yourself to be transported to Victorian England as this classic tale comes to life. A Christmas Carol is guaranteed to inspire and uplift you and is the perfect way to celebrate the magic of the season. 
  4. The Nutcracker: December 5-7, The Colonial Theater. Going to this ballet is one of my family’s own holiday traditions and it never disappoints.  Take your family to the Colonial and be mesmerized by these talented dancers as they tell the story of Clara and her magical Christmas Eve dream. 
  5. Stockbridge Main Street at Christmas: December 6-7. Bring the family to Stockbridge and experience the magic of small town New England. This beloved community event transforms Main Street into an enchanting destination that offers something for everyone in the whole family. Come get transported back to the days of yore, and we’ll toast the season together.
  6. Holiday Marketplace: December 6-7, Berkshire Botanical Gardens. A popular event amongst locals, the Holiday Marketplace is a wonderful opportunity to shop from regional artisan vendors for unique gifts and holiday blooming plants. 
  7. Holiday Shop, Sip & Stroll:  December 13, Downtown Great Barrington.  The Stroll features dozens of free activities like crafts, games with prizes, encounters with holiday characters and more! Fun for the whole family and bound to put you in the holiday spirit!
  8. Holiday Shindy: December 13, Downtown Pittsfield. A much anticipated artisan fair, the Holiday Shindy has been going strong for the past 18 years and is always a magical shopping experience. Support our local farms and vendors while picking out special gifts for your loved ones. 
  9. It’s a Wonderful Life:  December 19, Mahawie Theater. Indulge in nostalgia while enjoying a free screening of this holiday favorite. This annual traditional screening can’t be missed!
  10. The Mount Holiday House Tours: Dates are to be announced, but the estate will be decorated for the holidays.
  11. Norman Rockwell Museum Guided Tours: Dates are to be announced. Tours focus on the artist's life and works, including his "Home for the Holidays" exhibit.
Get Exploring!