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Things to do in Berkshires + Western Massachusetts

From classic must-see sights to insider hot spots and local haunts, there are countless things to do in Berkshires + Western Massachusetts. How do you decide? Start with our travel guide and get our favorite Berkshires + Western Massachusetts attractions and activities—shops, museums, parks, nightclubs, coffee shops, tours, and more.

Our international team of editors and writers handpick the best things to do in Berkshires + Western Massachusetts to help travelers discover authentic, local experiences. Whether a hidden boutique with handcrafted products, a popular local festival, a bakery with a cult following, or a picnic-worthy park, Travel + Leisure guides the way, providing information and inspiration. From beaches and bars to cultural attractions and up-and-coming neighborhoods, our list will help you make the most of your romantic getaway, family vacation, or trip with friends. Below find Travel + Leisure’s top picks for what to do in Berkshires + Western Massachusetts.

  • Bear Swamp Orchard

    An ultra-green picking experience can be had at this intimate orchard in western Massachusetts that has offered PYO only since 2008. Orchardists Je... More
  • Bizarro

    Brace Yourself: There are three versions of the Bizarro coaster in the U.S.: one at Darien Lake in New York State, one at Six Flags American in Mar... More
  • Brimfield Antique Show

    Three times a year, the 18th-century town of Brimfield is overwhelmed by a series of antiques shows set up in humongous open fields for a six-day s... More
  • Buggy Whip Antiques

    Four centuries of American life gather under one roof in a retired buggy whip factory in Southfield, which now rounds up some 35 antique sellers. F... More
  • Dr. Seuss National Memorial Sculpture Garden

    While you’re at the Springfield Museums, stop by this sculpture garden to see the Cat in the Hat; the author was born in town. More
  • Fine Arts Center, University of Massachusetts at Amherst

    The concrete box, designed by architects Kevin Roche and John Dinkeloo in 1975, contains a concert hall and a little-known contemporary art gallery... More
  • Great Falls Discovery Center

    Head north to Turners Falls and bike the four-mile Canalside Rail Trail over the Connecticut River. More
  • Hancock Shaker Village

    Head west along the Mass Pike toward Hancock Shaker Village, the Shaker Museum & Library in Old Chatham, and what is left of the buildings that onc... More
  • MASS MoCA

    The museum is a village in miniature spread over 13 acres, with 26 buildings dedicated to art, music, dance, film, and theater. The institution can... More
  • Massachusetts State Fair

    Opens late September. More
  • Mead Art Museum

    The institution is known as a compact bastion of American treasures - Robert Henri's Salome (1909) is housed here. The museum has recently acquired... More
  • Mount Holyoke College Art Museum

    The campus museum boasts 10 galleries dedicated to Asian, Renaissance, and contemporary art. More
  • Mount Sugarloaf State Reservation

    The mountain's peak offers an incredible vista of the Connecticut River snaking through the valley. More
  • Museums10

    A collective of 10 of the area's best museums. More
  • Naismith Memorial Basketball Hall of Fame

    The museum has everything hoop-related. More

Explore things to do in Massachusetts for more options.

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