RSS

Winter Festivals

The Berkshires is abound in fun-filled annual festivals celebrating everything from agricultural harvests to the gifted artisans of this region. Some are steeped in history while others are new to the local culture. All offer something unique for the visitor and are very popular attractions for this region. Whether it’s the Fall Foliage Festival or the Berkshire Fermentation Festival, the food and entertainment is exemplary.

Annual Winter Festivals in the Berkshires

  • Stockbridge Main Street at Christmas

    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 Main St. at Christmas. Read more

  • Festival of Trees at the Berkshire Museum

    Annual Holiday event in November that features decorated trees displayed throughout the galleries. Read more

  • First Fridays Artswalk

    First Fridays Artswalk kicks off a month of art February through December displayed indoors in galleries, retail & hospitality businesses along the North St. Read more

  • Hancock Holidays

    On weekends, after Thanksgiving and in December, we have special programming. Crafts, live music, story times, performances, great food, spirited drinks, and more. The grounds are open for select hours. Get your tickets and explore at your leisure. Read more

  • Winterlights at Naumkeag

    This holiday season, the gardens at the popular historic homes Naumkeag in Stockbridge will sparkle with thousands of shimmering holiday lights. Each weekend features performances and activities for the whole family, from the young to the young at he Read more

  • 10x10 Uptown Arts Festival

    New theatre, art, comedy, dance, music, and more in the middle of winter? You bet!  From new theatre and art shows to comedy and spoken word, 10×10 warms up the Berkshires winter with hot new performances, art and more. Read more

Check out our calendar of events specifically showcasing this season's festivals!

Sorry, no results.

View more Search Events
  • Courtyard Lenox bar.jpg

    Drink, Dine, Decompress

    What better way to end your long day than with a cocktail and appetizer... in bed! the Courtyard by Marriott Lenox offers every convenience under one roof! Read more

  • Courtyard Marriott Lenox Girlfriend Getaway

    Girlfriend Getaway

    The Berkshires is the perfect place for a girlfriends getaway...top notch shopping, amazing restaurants and comfortable lodging. Read more

  • Yankee Suites Extended Stays Pittsfield Ma

    Extended Stays

    Looking to stay a week? Month? Year? Yankee Suites Extended Stays offers fully equipped condo-style living in downtown Pittsfield. Read more

  • Yankee Inn

    Book an in-room massage

    Upgrade your next stay with the ultimate indulgence- an in room massage at the Yankee Inn Read more

Have a question about your trip to the Berkshires?

Ask Us

be in the know

Stay up to date with:

•Events •New and noteworthy happenings 
•Exclusive offers delivered to your inbox each month!

Sign Up