Connecticut’s largest county, Litchfield, is also its least populous. Tucked in the northwest corner of the state, bordering both New York and Massachusetts, Litchfield is fairly rural with lots of farmland and small town centers that look and feel like they were plucked from a Norman Rockwell painting—which they certainly could have been, as Rockwell’s home was not far away in Stockbridge, Mass. 

Connecticut has over 500 miles of dirt roads and you’ll find the majority of them here in Litchfield. In the summer this is an area that city people retreat to, to breathe the fresh air of the outdoors that the county offers with its camping and hiking; taking advantage of the Berkshire Mountains, the Housatonic River, the antique stores and the farmers markets. 

In the winter, Litchfield seems more isolated and it becomes apparent why private schools like Kent and Hotchkiss are situated in an area that is so quiet, removed from anything that might distract from their studies. It’s a quiet time of year; the farmers’ fields seem larger and the woods seem deeper without their foliage, and the deer have fewer places to hide.

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Guide to the Northeast Brett Klein lives in Connecticut and works in New York, but prefers small town life and his homestate of Maine. Any chance to get rural is a mental vacation. Follow Klein on Tumblr at The Coast is Clear. His curatorial collection of Americana, rural life, other artists and ephemera can be seen on Tumblr at Tons of Land.