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.

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

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Annual Fall Festivals in the Berkshires

Heres a list of the upcoming festivals this season!

  • Freshgrass Festival

    September 20-22, 2019- Surrounded by the beautiful backdrop of the Berkshire mountains in northwestern Massachusetts, the two day festival takes place at Mass MoCA, promoting innovative grassroots music. Read more

  • Berkshire Botanical Garden Harvest Festival

    October 6th and 7th- A festival highlighting all things autumnal at the Berkshire Botanical Garden's Harvest Festival. Over 100 craft & food vendors plus family & farm activities. Read more

  • Fall Folliage Festival

    A parade on the first weekend of October that starts on Curran Memorial Highway. It runs down Main Street and ends on Ashland Street. 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

  • Hawthorne Valley Farm Fall Festival

    Over the years, the Festival has grown into a seasonal favorite with over 3,000 people attending. Read more

  • Josh Billings Triathlon

    September 16, 2018- 500 teams bike 27M from Great Barrington to Lenox, paddle 5M at the Stockbridge Bowl, and run 6M to Tanglewood with awards, band, food, kid's run all at Tanglewood. Read more

  • The Big E

    The Big E, also known as The Eastern States Exposition, is billed as "New England's Great State fair". It is the largest agricultural event on the eastern seaboard and the seventh-largest fair in the nation. Read more

  • Lenox Apple Squeeze

    One of the newer and much celebrated annual traditions with a lot of popularity celebrating the apple harvest with a lot of food and artisan vendors in addition to great live music. Read more

  • Lee Founder's Weekend

    Celebrating Lee's founding the second weekend of September. Food, fair, parade, and a grand Latino Festival. Read more

  • 3rd Thursday 2019- Downtown Pittsfield

    This free, family- friendly, cultural street festival offering live music and performances, local food and craft vendors, street performers, and more, runs every third Thursday from May-October. Read more

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