Located between Boston and New York, Connecticut is the third smallest state in the U.S., stretching just 100 miles east to west and 60 miles north to south. Driving across its varied landscape takes about two hours, transporting travelers from country roads and estates to seaside towns and lighthouses.

In the northwest corner of the state, colonial villages dot farmland and the Housatonic River curves past the Appalachian Trail. The peak foliage season runs from early October to early November, when rolling hills throughout Litchfield County turn bright with fall color. In Woodbury and Putnam, antique aficionados shop storefront boutiques specializing in period furnishings and art. Hopkins…

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