While crossing the river, the state highway passes through a sliver of Chesterfield County before entering the independent city of Colonial Heights.

SR 144 passes through a commercial area that includes the Southpark Mall and the world's largest Arby's restaurant.

West of the freeway, SR 144 reaches the western end of Temple Avenue and turns north to run concurrently with US 1 and US 301 along the city's main north–south thoroughfare, Boulevard.

There, the state highway has a brief concurrency with four-lane undivided SR 10 (West Hundred Road) to cross the North End Subdivision rail line.

[5] In 1943, it was extended west along SR 407 for a short length, then 5.3 miles (8.5 km) south to US 1 and US 301 using the routing of what was at the time State Route 621, a secondary road; the Commonwealth Transportation Board's justification for replacing it with SR 144 was that it was "a heavily traveled feeder road serving a rapidly developing portion of [Chesterfield County]".