From Droitwich to Low Hill (south of Kidderminster) the road is probably ancient, as it is referred to in the Saxon charter for Whitlinge (in Hartlebury) dated AD 980 as a stræte.

[2] North of Kidderminster it was a 'way' in the Saxon bounds[clarification needed] of Wolverley before being joined by the great street at Shatterford.

At Shatterford, the Prior of Worcester was authorised to assart (i.e. to clear) 100 acres (0.40 km2) of wood and heath "for the greater security of persons going through the said pass".

The stretch immediately beyond Sutton Cross was part of the Madeley turnpike district, going to the Bucks Head on Watling Street.

This was turnpiked in 1764, continuing southeast to the New Inn on Rudge Heath, but that stretch of road was evidently not improved until the 1960s, when it was upgraded to become the B4176.

The northern terminus was altered in 1827 when the road from Balls Hill in Dawley to Bucks Head was discontinued in favour of an alternative route to Watling Street.