In the early days of the Tehachapi Valley traveling was arduous as there were only trails and wagon tracks, a few toll roads and the stage routes. The road to Bakersfield from Tehachapi followed the current Woodford - Tehachapi Road, curving and climbing along the hillsides and skirting the Tehachapi Loop before winding eventually to the valley floor to reach Bakersfield.
To improve traveling to the east, on July 18, 1913 a bond issue was approved for $2,500,000 and in 1916 a road 28.2 miles was completed from Tehachapi to Mojave.
The construction of a modern two-lane highway to connect from Tehachapi to Bakersfield and Mojave began in 1937, with prison labor, at the Bear Mountain Ranch which was on the south side of highway 58 between Hart Flat and the Caliente cutoff. Construction continued until 1943 when restrictions on materials due to World War II stopped the project. The final link of the new road was finally completed on October 31, 1948 when the section between Keene and Tehachapi and points east was finished.
In the early 1960s, construction of the 58 freeway was started in the San Joaquin Valley and proceeded east, partially following the old State Highway 466. Due to rerouting in certain areas, it wasn't until 1968 that it reached Tehachapi and took quite few more years before it reached Mojave.
Route 202, today following Tucker Road and Valley Boulevard, was constructed in the latter half of the 1960s to provide a more direct route from highway 58 to the prison when the new medium security prison was built.
As Tehachapi has experienced major growth in more recent years, the City and County has widened roads, installed curbs and sidewalks and added connecting links to aid traffic flow, such as Red Apple Road and the extension of Valley Boulevard through to Dennison Road.