On September 26, 1939, this route was renumbered from part of SH 14. Prior to June 28, 1989, SH 289 began north of downtown Dallas, Texas in the Oak Lawn neighborhood at an 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. Less than a mile later at an intersection with Oak Lawn Avenue, the highway designation turned northeast up Oak Lawn, which it followed into Highland Park. There it was known as Oak Lawn Avenue until an intersection with Armstrong Parkway, where it became Preston Road. On October 30, 1958, SH 289 extended northward 3.6 miles. Preston Road is one of the most congested highways in the Dallas/Fort Worth Metroplex; however, due to urban growth along the highway there is minimal room to add additional lanes, and no means to upgrade the road to freeway status without incurring significant cost to demolish businesses along the path. Instead, the nearby Dallas North Tollway generally parallels Preston Road. On June 28, 1989, the section of SH 289 from Loop 12 to a deleted section of Loop 354 was cancelled. Before that, SH 289 began north of downtownDallas, Texas in the Oak Lawn neighborhood at an 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. Less than a mile later at an intersection with Oak Lawn Avenue, the highway designation turned northeast up Oak Lawn, which it followed into Highland Park. There it was known as Oak Lawn Avenue until an intersection with Armstrong Parkway, where it became Preston Road. 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. SH 289 officially ends at Elks Boulevard; the actual road continues for another 3–4 miles before ending at a local street in the Preston Bend community. This provides another access route to North Texas Regional Airport, which has been proposed as a third airport for the DFW area. Approximately US$63 million in bonds were sold by Grayson County, Texas. The Texas Department of Transportation has promised US$85 million in reimbursements for the bonds sold by the county.
Business State Highway 289-C is a business loop that runs on the former routing of SH 289 through Celina. The route was bypassed in 1969 by SH 289 and redesignated Loop 483. Loop 483 was redesignated as Business SH 289-C on June 21, 1990.
Prosper bypass
Business State Highway 289-D is a business loop that runs on the former routing of SH 289 through Prosper. The route was bypassed in 1966 by SH 289 and redesignated Loop 439. Loop 439 was redesignated as Business SH 289-D on June 21, 1990. On May 28, 2009 the section from FM 1193 north to FM 1461 was returned to Prosper and Celina.