The origins of Maitland's main street go back to the earliest European settlement: it was the jumping-off point for those headed for the upper Hunter, the squatting leases of the Liverpool and Western plains and even southern Queensland.

Maitland was the principal gateway to a vast area about to be colonised and developed.

From the 1820s the volume of traffic from Newcastle and Morpeth through Maitland was considerable. A track was worn by bullock teams driven by people travelling inland to establish new farms or service existing ones.

It is possible that the track followed a songline developed over the millennia by local Aboriginal people, as is known to have occurred elsewhere. Between the river and the wetland of Louth Park, the relatively high round of the natural river-side levee would have been suited to such a track.

The track as it developed in the 1820s was informal and unsurveyed. It traversed the land occupied and farmed by the former convicts who made up the first European settlers of Maitland.

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When the economy of the inland became established, wool and other agricultural products came back via Maitland and Morpeth to Sydney and the world.

By the 1830s, High St was a busy route, dozens of bullock teams passing through on some days.

From the Port of Maitland at today's Smyth Park the track followed the shortest route to 'The Falls' just above the present Belmore Bridge. Here the road divided, one track heading to Paterson and the other across Veterans Flat to Campbells Hill, the upper Hunter and the interior.

There were large trees to avoid, and after they were felled their stumps remained until they rotted or were burnt out of existence. Some straightening of the route would have become possible.

Between the Port and Hunter Street, a distance of 400 yards, the track became lined with buildings - inns, blacksmiths, saddleries and all manner of shops. This was the area of Maitland's original Central Business District. Other buildings straggled along High St north and south of this dense cluster.

The track initially was more undulating than it is now. Natural depressions in the ground became tiny creeks which took flows to the river after rain and (when flooding occurred) river water onto the floodplain. These depressions were often boggy and difficult to traverse.

Gradually, they were filled in and some were piped to the river: one was on the alignment of Free Church St. There were others.

High Street, for decades vital to the developing inland, remained muddy for many years, but investments were made in it. Timber footpaths were created for ease of pedestrian movement, and troughs for bullocks and horses to drink from. Eventually it was gravelled and later again hard-topped.