7 Most Pleasant Restaurants for Gourmands in Cheshire, Massachusetts

Cheshire, Massachusetts belongs on your restaurant bucket list. Super food secrets seem to be hidding in plain sight.

Trust us: Cheshire, Massachusetts actually ain’t no flyover libertarian land, friendly ladies and gentlemen of earth. Yet, impressing food snobs from New York City is not a prerogative. Old school Massachusettsians grasp what is truly good.

This is the type of smaller Massachusetts town that Steven Tyler would appreciate and that makes us proud. So many classic recipes will come from families that go back generations around Cheshire, Massachusetts.

What are they baking these days with lobsters and cantaloupes? Anticipate astonishment. To all folks who are fans of the Americana aesthetic, you will love the feeding troughs that rock vintage diner decor. Meanwhile in the center of town, modern places have poured money into chic interior designs and booming sound systems. The goal is to entice vain millennials to take selfies and make their friends envious on Facebook. There’s nothing like free promotion!

The dining clubs below have all the tastiness and variety you need to eat right and live right. You will be so happy you decided to feast in Cheshire, Massachusetts. Friends from Manhattan, join us for the best cuisine in Red Sox Nation.

District Kitchen & Bar


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40 West St
Pittsfield, MA 01201