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Top Things to Do in Pittsfield, MA Places to Visit in Pittsfield All Things to Do Tours Outdoor Activities Attractions Concerts & Shows Food & Drink Shopping Traveller Resources View map Top Attractions in Pittsfield Sort by: 1. Swing by Hot Dog Ranch for one of our fun events. You will walk past cascading streams Things To Do Tips and articles Bear Swamp Orchard An ultra-green picking experience can be had at this intimate orchard in western Massachusetts that … Search for restaurants, hotels, museums and more. Top things to do in Pittsfield, MA : Discover the best activities this weekend and beyond in Pittsfield with deals of up to 70% off. 1. The creators of this market aim to And right outside our front door you’ll find a neighborhood sprinkled with restaurants, culture, shopping, and history. Whether you're a local, new in town or just cruising through we've got loads of great tips and events. PITTSFIELD ATTRACTIONS Albany Berkshire Ballet51 North Street, Pittsfield, Ma. 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