Cumberland Highway then follows Hart Drive in a southwesterly direction, changing name to Freame Street once it crosses under the North Shore and Western railway line in Wentworthville, and then intersects with and changes name to Emert Street shortly afterwards, before reaching the intersection with Great Western Highway.

Cumberland Highway was created from a series of pre-existing roads through western and north-western suburban Sydney, not all contiguous at the time, with Pennant Hills Road in particular already declared as a major arterial route 60 years before it was eventually incorporated into the modern-day highway.

The construction of a ring road around Parramatta and increasing traffic levels in western Sydney in the late 1970s became the precursor to today's highway.

State Highway 13 eventually assumed the role of a western bypass of Sydney, made official when it was declared as part of Ring Road 5 in 1964.

With the conversion to the newer alphanumeric system in 2013, Cumberland Highway was re-designated part of route A28, replacing the last remnant of Metroads 6 and 7 along Pennant Hills Road.

[11] Since its opening, all trucks and buses over 12.5 metres long or over 2.8 metres clearance height (except vehicles transporting dangerous goods, oversize vehicles, or that have a genuine destination only accessible via Pennant Hills Road) travelling between the M1 and M2 are forbidden to use Pennant Hills Road and must use the NorthConnex tunnels instead.

A fine of A$194 with no demerit points will also be imposed on truck and bus drivers detected (with the use of cameras mounted on gantries) using Pennant Hills Road with the traffic flow.