Although it began as a track across farmland, High Street was the principal road to the Upper Hunter Valley and northern New South Wales from the 1820s until the town was bypassed in modern times.
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In the beginning it gave access to the estates of the Upper Hunter but in the late 1830s it led the squatters and their flocks north to the great untouched pastures of the colony.
As these farmers and graziers prospered they sent their produce back down the track through Maitland to be shipped from Morpeth and Newcastle and the business people of High Street prospered as never before, particularly in the retail and wholesale trades.
Eventually the bullock waggons gave way to steam trains but until the Great Northern Railway reached Singleton in 1863, making that town the temporary railhead, the bullockies and their teams dominated the life of High Street.
Dozens of these teams, drawing drays or waggons, would pass through on a single day bringing wool from stations as distant as Roma in Queensland to Morpeth.
They would then return with goods from the steamers and take on supplies at the West Maitland stores. Even when the teams ceased to come from the distant interior, they were still to be seen bringing the produce of the Hunter district and supplying the farmers from Wollombi in the south, to Paterson in the north.
Consequently High Street was always a highway although this function was less important between the coming of the railway and the age of the internal combustion engine.
In the 20th century, as trucks and cars came to dominate the transport scene, heavy traffic on the New England Highway once again made High Street a thoroughfare for long distance travel.
