Along this stretch of highway, there are 14 structures and buildings. Insofar as the National Register and historic preservation are concerned, eight of those are considered contributing structures to the listing and six are considered non-contributing. There are also 12 highway bridges found along the segment and a box culvert; six of the bridges are considered contributing to the National Register listing, as is the box culvert. Six of the bridges have been replaced since the historic period, and all of the bridges are constructed from concrete. The bridges have various lengths and support structure. The box culvert along the segment of road measures by wide and was built as part of the road's foundation. This particular box culvert, like many, usually went unnoticed by travelers along the road. The section of pavement between Pontiac and Cayuga was part of a larger section of the roadway that began north of Cayuga in Gardner. This entire section was built in 1943 after large parts of Route 66 became badly deteriorated during the mid-1940s. The portion of the roadway that extended south of Pontiac to the newly constructed bypass at Bloomington-Normal was constructed during the early 1940s.