Prior to June 28, 1989, SH 289 began north of downtown Dallas in the Oak Lawn neighborhood at its intersection with Pearl Street.

From there, the highway designation followed Cedar Springs Road northeast for less than a block, and upon an intersection with Maple Avenue, ran northwest up that street.

There, it was known as Oak Lawn Avenue until an intersection with Armstrong Parkway, where it became Preston Road.

Preston Road is one of the most congested highways in the Dallas/Fort Worth Metroplex, but due to urban growth along the highway, room to add additional lanes is minimal, and no means exist to upgrade the road to freeway status without incurring significant cost to demolish businesses along the path.

On November 19, 2009, an extension of SH 289 was completed from its previous terminus at SH 56 northward to a new connection with Farm to Market Road 120 near Pottsboro, Texas, another segment of the old Preston Trail, which ends on the south shore of Lake Texoma.

The Texas Department of Transportation has promised US$85 million in reimbursements for the bonds sold by the county.