Fairs and Festivals

Fairs & Festivals brighten the Berkshires every season of the year

In a landscape like this with so much natural beauty, history, creative and performing artists, craftsmen, food purveyors, wine and beer makers, there are lots of reasons and occasions to hold celebrations of every kind. Year-round this part of Massachusetts is filled with fairs, festivals and other events highlighting the richness found here. Each fall brings with it a special blend of activities for the whole family, as do the holidays and warmer months. Come for a family getaway to this sweet spot in New England and be delighted.

The Dragon Boat Festival. Courtesy of Massachusetts Office of Travel & Tourism. Photo by Kyle Klein

Our picks

  • Lenox, MA

    BSO - Tanglewood

    Surround yourself with the sounds of music at this famous festival in the Berkshires

    The sound of music, in all its spell-binding forms, is everywhere at Tanglewood, summer home of the Boston Symphony Orchestra and site of one of the world’s most beloved music festivals. Whether your tastes run to Beethoven, or to James Taylor – or to the movies! – you will find something to engage the music-lover in you at this magnificent property in the Berkshires. The festival runs from late June through August, this year featuring everything from Kool and The Gang and “Jurassic Park in Concert” to chamber-music ensembles, guest artists Yo-Yo Ma and Joshua Bell, and an all-Strauss program with leading soprano Renee Fleming. Tanglewood also offers summer guided tours. Dining options include elegant picnics, a bistro buffet and three-course dinners at Highwood Manor House.

    297 West Street 617-266-1200

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