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Fall 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.

Fall Festivals in the Berkshires

  • Lenox Apple Squeeze

    September 22-23, 2018- 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. 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. 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. 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. more

  • Lee Founder's Weekend

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

  • 3rd Thursday

    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. 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. more

  • Hawthorne Valley Farm Fall Festival

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

  • Freshgrass Festival

    September 14-16, 2018- 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. more

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

  • Greylock Works

    FESTIVE Holiday Market

    FESTIVE Holiday Market! FALL INTO THE BERKSHIRES @ gWorks Our FESTIVE 2018 holiday marketplace will be Saturday, NOVEMBER 17th! Join us for Greylock WORKS’ 2nd annual Fall FESTIVE – a handmade holiday market celebrating local food and design from t more

    Nov 17, 2018

    10:30 AM

    Greylock WORKS

    North Adams & Williamstown

  • Naumkeag Winter Lights.jpg

    Winterlights: Naumkeag

    Premiering this holiday season, the garden at one of our most popular historic homes, Naumkeag in Stockbridge will be illuminated with thousands of shimmering holiday lights and designed light installations. Each weekend features performances and act more

    Nov 23, 2018

    5:00 PM

    Naumkeag

  • Naumkeag Winter Lights.jpg

    Winterlights: Naumkeag

    Premiering this holiday season, the garden at one of our most popular historic homes, Naumkeag in Stockbridge will be illuminated with thousands of shimmering holiday lights and designed light installations. Each weekend features performances and act more

    Nov 23, 2018

    5:00 PM

    Naumkeag

  • Naumkeag Winter Lights.jpg

    Winterlights: Naumkeag

    Premiering this holiday season, the garden at one of our most popular historic homes, Naumkeag in Stockbridge will be illuminated with thousands of shimmering holiday lights and designed light installations. Each weekend features performances and act more

    Nov 24, 2018

    5:00 PM

    Naumkeag

  • Naumkeag Winter Lights.jpg

    Winterlights: Naumkeag

    Premiering this holiday season, the garden at one of our most popular historic homes, Naumkeag in Stockbridge will be illuminated with thousands of shimmering holiday lights and designed light installations. Each weekend features performances and act more

    Nov 24, 2018

    5:00 PM

    Naumkeag

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