This part of High Street was built between 1850 and 1885, and is lined with masonry buildings in Italianate and Second Empire styles.

[2][3] The district was extended a third time, in 2008, adding a complex of three buildings at Dwight and Maple Streets that now houses the Holyoke Health Center.

In that year, investors from Boston purchased a mill privilege on the Connecticut River, on which they proceeded to develop the industrial sites that fueled the growth of the city.

Many buildings on High Street in the 1986 district boundaries date to this period of rapid growth, which was completely built out by 1880.

[4] Between 1880 and 1930 the area northeast of the early cluster of commercial buildings was developed, spurred by the construction of City Hall in the 1870s, and by the extension of streetcars line for the Holyoke Street Railway in the latter half of the 19th century.