New England's Connecticut River meanders 410 miles south from the Canadian border to Long Island Sound. After thousands of years of peaceful habitation by Indigenous people came 400 years of development around European settlements, farmsteads, shipping ports, and manufacturing mills. Farmers, boatbuilders, quarrymen, and industrialists benefitted from the river valley's fertile plains, geological resources, and waterpower. Ready access to markets at Boston, New York, the West Indies, and Europe fueled the growth of the valley's towns and major cities such as Hartford and Springfield. The valley has been home to consequential social reformers, authors, and intellectuals. Its bucolic settings attracted artists who came to the renowned colonies at Cornish and Lyme, steamboat tourists, and urban transplants with modern lifestyles. The most important houses they built, many of which are designated national historic landmarks and open to the public, and some newly discovered properties are highlighted here for their architectural significance and rich historical associations.