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Westward expansion in the New World began along the meandering Connecticut River. Dutch explorer Adrian Block first explored the area in 1614, and in 1633 a trading post was set up in what is now Hartford. Within five years, throngs of restive Massachusetts Bay colonists had settled in this fertile valley. What followed was more than three centuries of shipbuilding, shad hauling, and river trading with ports as far away as the West Indies and the Mediterranean.

Less touristy than the coast and northwest hills, the Connecticut River valley is a swath of small villages and uncrowded state parks punctuated by a few small cities and a large one: the capital city of Hartford. South of Hartford, with the exception of industrial Middletown, genuinely quaint hamlets vie for attention with antiques shops, scenic drives, and romantic French restaurants and country inns.