The highway was established in 1927, originally going from Manila to Greendale Junction and continuing south to Vernal.

However, in 1981, the portion from Vernal to Greendale Junction was truncated in order to designate that road a part of US-191.

The route begins at the junction of US-191 on the southern boundary of the Flaming Gorge National Recreation Area, southwest of Dutch John.

Past Sheep Creek Loop Road, the route begins a more unpredictable path with many twists and turns, though remaining in a general northwest direction.

[5] Two major realignments through the Ashley National Forest were made in 1966 and 1971, the first moving SR-44 to the northeast between a point south of Carter Creek and near Summit Springs, and the second moving it east between a point east of Summit Springs and Sheep Creek Gap.