In his 1771 book "Rural Economy of Yorkshire" Arthur Young describes Hambleton Street.
"You are obliged to cross the moors they call Black Hambleton, over which the road runs in narrow hollows that admit a south country chaise (Cart) with some difficulty, that I reckon this part of the journey made a hazard of my neck. The going down into Cleveland is beyond all description, terrible, you go through such steep, rough, narrow, rock precipices, that I would sincerely advise you to go a hundred miles to escape it".
"Of all the ancient trackways running roughly north and south across the high moors, the most notable and for long the dominant road in the area wads Hambleton Street.
It is still largely in it's original condition, of a major trade artery of prehistoric times. Crossing the Tees at Yarm it climbs on to the moor-top at Scarth Nick, skirts Osmotherly, and then follows the western escarpent of the Hambleton Hills over Black Hambleton, southwards to Boltby Bank Top and Sutton Bank Top. Here it forks. One branch descended via Oldstead to Coxwold, Crayke and York. The other and probably more ancient branch, swung eastwards approximatly along the line of the modern road A170 as far as Tom Smith's Cross and then by 'Ampleforth High Street' to Oswaldkirk Bank Top, Stonegrave, Hovingham and Malton. Thence ancient travellers could follow it south again over the Wolds and across the Humber to Brough and so over the Lincolnshire Wolds".
A History of Helmsley Reviaulx and District.
Helmsley & Area Group of the Yorkshire Archaeological Society
Stonegate Press 1963