The entire highway serves as a bypass of downtown Knoxville and as a direct connector to the University of Tennessee (UT) campus and athletic facilities.

Serving as the primary means of access to facilities such as Neyland Stadium and Thompson–Boling Arena, the route experiences congestion on game days, with a contraflow lane reversal implemented to mitigate this.

[4] It also serves as a spur into downtown and provides access to a number of local landmarks and historic sites, including the Blount Mansion and James White's Fort.

[8] SR 158 begins as a secondary highway known as Neyland Drive at an intersection with Kingston Pike on the western edge of the University of Tennessee (UT) campus.

[9] The road passes by the UTK Sorority Village before meeting the north bank of the Tennessee River and running alongside a Norfolk Southern Railway track.

[10] The route then turns southeast and passes underneath the J. E. "Buck" Carnes Bridge, which carries US 129 (Alcoa Highway), a major freeway in Knoxville, across the river.

The road passes by a number of other UT facilities, including the university's veterinary school, before gradually turning east along the State Botanical Garden of Tennessee and crossing Third Creek.

[9][11] Turning north-northeast, the road passes under a Norfolk Southern crossing of the Tennessee River,[10] and has a signalized intersection with Lake Loudoun Boulevard.

SR 158 then passes directly under the Gay Street Bridge, where the controlled-access portion begins at an eastbound-only exit for Volunteer Landing, a public park.

[9][11] Turning sharply north, the highway transitions away from the riverbank, passes by the Blount Mansion and James White's Fort, and underneath the Hill Avenue Bridge.

[23] At the same time, the University of Tennessee and the city of Knoxville were looking to relieve game-day traffic congestion around Neyland Stadium, which was then called Shields–Watkins Field.

On October 23, 1950, Tennessee Governor Gordon Browning instructed state highway commissioner Charles F. Wayland Jr. to begin work on a two-lane extension of Front Street, initially known as Lakefront Drive, to Kingston Pike.

[40] After multiple weather-related delays, this section opened to traffic on September 15, 1973,[3] and was dedicated in a ceremony by Governor Winfield Dunn and Knoxville Mayor Kyle Testerman four days later.

The eastern terminus of SR 158 with I-40 quickly developed a high crash rate, largely due to left-hand entrance and exit ramps on I-40 westbound.

[52] Additional public hearings were held between November 1995 and January 2000, and the environmental impact statement for the project was approved by the FHWA on February 28, 2002.

[56] For the next part of the first phase, the James White Parkway portion of SR 158 was closed to all traffic between December 17, 2006, and September 21, 2007, to accelerate the reconstruction of this segment.

[57][58] The northern portion of this stretch was widened, the Church Avenue bridge was replaced with the transit center viaduct, and a new ramp from I-40 eastbound to SR 158 westbound was constructed.

[64] From March 1997 to January 2000, a connector between SR 158 and the South Knoxville Bridge was constructed, requiring expansion of the interchange with Hall of Fame Drive and Cumberland Avenue.

[66] Between April 2015 and August 2017, the city of Knoxville undertook a streetscaping project which transformed a short stretch of Cumberland Avenue east of the western terminus of SR 158 from an urban thoroughfare into a pedestrian and bike friendly corridor.