The region was platted by William Robbins, the founder of Hinsdale, in 1865. The Chicago, Burlington and Quincy Railroad's (CB&Q) passenger station prompted several small businesses to develop across the street. Fifty-eight of the listed buildings were built for commerce, three for government, and nine for transportation. The remaining building is a theater. The shops are densely clustered in orthogonal patterns, and are mostly found on the south side of the railway tracks. The government buildings, including the Village Hall (Hinsdale Memorial Building) and U.S. Post Office are on the north side.
An article entitled "Hinsdale the Beautiful" in Campbell's Illustrated Journal prompted city officials to further beautify the city. The first major project was a state-of-the-art train station, which was designed by CB&Q architect Walter Theodore Krausch. The station became a model for the future construction of other stations on the line. The region north of the tracks became the next target, focusing on the Railroad Park (modern day Burlington Park). Commercial demand spiked in the early 20th century, even causing some gablefront residential buildings to be rezoned as commercial. The 1200-seat Hinsdale Theater was constructed in 1925 for $160,000. Chain retailers began to move into the downtown district starting in the 1920s, starting with a Loblaw food chain in 1929 (which was purchased in 1932 by the Jewel Tea Company). A Piggly Wiggly and a Walgreens also moved in during this period. In the 1920s, the city of Hinsdale overhead plans by a local car dealership to build the largest automobile garage "east of the Mississippi". To curb this plan, the city bought the proposed site and constructed a building dedicated to those who served and died in World War I. Construction on the Memorial Building finished in 1927.
Hinsdale is notorious for the aggressive teardown policies pursued by real estate agencies in its residential districts, but the commercial district has remain intact. The earliest buildings are on First and Washington Streets, which date from the 1880s and are in the Late Victorian, Italianate, and Queen Anne Styles. Colonial and Renaissance Revivals featured in early 20th century buildings until the Hinsdale Plan of 1923 dictated the use of Georgian Revival architecture. Eight of the properties were built after 1955. The district is served by three asphalt-paved parking lots.
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