In the early decades of the 19th century, New Preston housed an iron works, as well as manufacturers of twine, hats, cheese boxes, ax handles, shoes, and harnesses.

With the arrival of the Shepaug Railroad in 1872, passenger service was introduced between New Preston Station and New York City, which gave rise to the construction of summer homes and inns around the perimeter of Lake Waramaug.

In the mid-1980s, a transformation of the village center began with the opening by Timothy Mawson of a store specializing in antique gardening books and horticultural prints. Antique shops and other upscale retail establishments soon followed, and many of New Preston's historic commercial structures underwent renovation. By the mid 1990s, the village center had been completely made over into a picturesque, high-end retail destination.