[1] Its area was increased in 1992 to include the Hall and Bill building on North Street, built in 1889 by one of Willimantic's leading printers.

A 90-foot (27 m) drop further west on the Willimantic provided an additional source of water power, which was exploited in the early 19th century for the production of textiles.

Main Street, laid out in 1707, formed part of the major east-west Windham Turnpike established in 1799, bringing travelers through the village as well.

Later in the 19th century it became a railroad hub for the region, with two major railway lines crossing.

The oldest surviving commercial/industrial buildings in the district are a pair of early wood-frame mill buildings dating to the 1830s; they are located near the southwestern end of the district.