The road was first formed during the 1870s.[1] From the 1940s to the 1970s there were proposals for a railway line, the Haywards–Plimmerton Line, via this route.
In June 2010 a road assessment programme found that the Haywards Hill road was amongst the worst in the Wellington region, scoring only 2 out a possible 5.[2]
In November 2014 upgrades costing $30 million were announced, with $2.5 million of work starting immediately.[3]
Construction of an elevated interchange at the intersection of SH2 and SH58 at Haywards began in 2015 and was completed in 2017 for a cost of $42 million.[4] The project included a new park and ride car park at the adjacent Manor Park Railway Station and a pedestrian footbridge across SH2 to replace an existing underpass.[5] Further safety improvements are under construction and estimated to be complete by 2023. These include building median and road-side safety barriers, two new roundabouts at the intersections of Flightys Road and Moonshine Road identified as having high crash statistics, and widening parts of the road to four lanes.[6]
