Pittsfield

We’ve compiled the best of the best in Pittsfield - browse our top choices for the top things to see or do during your stay.

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  • Canoeing

    Empty Activity...

  • Hiking

    Ashuwillticook Rail Trail. Passing through the Hoosac River Valley, the paved 12.7-mile Ashuwillticook (pronounced Ash -oo-will-ti-cook)...

  • Skiing

    Bousquet Ski Area. On the tamer side of Berkshire ski options, Bousquet has 23 trails if you count merging slopes separately. Experts will...

  • Zip-Lining

    Ramblewild. One of the Northeast's largest tree-to-tree adventure parks, Ramblewild has eight trails with over a hundred physical challenges...