C onnecticut’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. lc1 lc2 lc3
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.

At-Large Guide to the Northeast, Brett Klein is a Maine native currently residing in Connecticut with his wife and two Maine Coon cats. Any chance to get rural is a mental vacation. Find him online at,, and
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If you are in Litchfield County, you can dart on over to the Norman Rockwell Museum located about an hour away.