The road was established as a stage coach route circa 1856, and paralleled a railroad line built in the late 1860s.

It was part of the main road connecting San Jose to Monterey, and incorporated parts of the historic route of El Camino Real connecting California's missions.
The towns of Gilroy and Morgan Hill sprang up as coach stops along it.
In one incident in July 1873, notorious highwayman Tiburcio Vásquez robbed Twenty-One Mile House, a hostel named for its location 21 miles from San Jose along the road, in what is now Morgan Hill.

The Northern California black walnut trees seen along this highway were planted by horticulturist Horace G. Keesling of San Jose.
While passing this way by camp wagon on a summer day in 1900, Keesling could find no road-side tree offering shade to relieve his sweltering family and horses, and he resolved to "plant shade" at his own costs.
This resulted in a 30-mile row of trees on each side of Monterey road from San Jose to Gilroy, a project that Keesling, assisted by his son Hayes Keesling, finished in 1911.
Except for stretches where urban growth and modern highway construction have required removal, these trees still provide the shade that Horace wanted.
There is a plaque that is hard to access located on the west side of Monterey Highway (next to the train tracks) in San Jose.

0.5 (one-half) mile south of Capitol Expressway, or 0.34 mile south of Senter Road, or 0.16 mile north of Skyway Drive.

The road became part of the state highway system in the early 1900s and, eventually, it became incorporated into U.S. Route 101 (US 101).
By the 1970s, as an expressway with only three lanes (for both directions combined) and high volumes of traffic, it had so many traffic accidents that it became known as "blood alley".

In 1973, the section from Monterey Road's southern terminus to Cochrane Road in Morgan Hill was realigned to a 6-lane freeway to the east, and in 1984, US 101 was realigned to a freeway to the east from Cochrane Road to County Route G10 (CR G10).
These two realignments restored Monterey Road as a separate road again.

Monterey Road continues to exist as a six-lane arterial road within San Jose and as a four-lane highway continuing to Gilroy,
and is used as an alternative route to the freeway for commuters.

Monterey Road north of CR G10 was once part of State Route 82 (SR 82), a route that was once US 101 before US 101 was realigned to the Bayshore Highway (now the Bayshore Freeway) to the east in the 1940s.
In 2013, a section of SR 82 was relinquished and given to the city of San Jose.
The road was established as a stage coach route circa 1856, and paralleled a railroad line built in the late 1860s.
It was part of the main road connecting San Jose to Monterey, and incorporated parts of the historic route of El Camino Real connecting California's missions. The towns of Gilroy and Morgan Hill sprang up as coach stops along it. In one incident in July 1873, notorious highwayman Tiburcio Vásquez robbed Twenty-One Mile House, a hostel named for its location 21 miles from San Jose along the road, in what is now Morgan Hill.
The Northern California black walnut trees seen along this highway were planted by horticulturist Horace G. Keesling of San Jose. While passing this way by camp wagon on a summer day in 1900, Keesling could find no road-side tree offering shade to relieve his sweltering family and horses, and he resolved to "plant shade" at his own costs. This resulted in a 30-mile row of trees on each side of Monterey road from San Jose to Gilroy, a project that Keesling, assisted by his son Hayes Keesling, finished in 1911. Except for stretches where urban growth and modern highway construction have required removal, these trees still provide the shade that Horace wanted. There is a plaque that is hard to access located on the west side of Monterey Highway (next to the train tracks) in San Jose.
0.5 (one-half) mile south of Capitol Expressway, or 0.34 mile south of Senter Road, or 0.16 mile north of Skyway Drive.
The road became part of the state highway system in the early 1900s and, eventually, it became incorporated into U.S. Route 101 (US 101). By the 1970s, as an expressway with only three lanes (for both directions combined) and high volumes of traffic, it had so many traffic accidents that it became known as "blood alley".
In 1973, the section from Monterey Road's southern terminus to Cochrane Road in Morgan Hill was realigned to a 6-lane freeway to the east, and in 1984, US 101 was realigned to a freeway to the east from Cochrane Road to County Route G10 (CR G10). These two realignments restored Monterey Road as a separate road again.
Monterey Road continues to exist as a six-lane arterial road within San Jose and as a four-lane highway continuing to Gilroy,
and is used as an alternative route to the freeway for commuters.
Monterey Road north of CR G10 was once part of State Route 82 (SR 82), a route that was once US 101 before US 101 was realigned to the Bayshore Highway (now the Bayshore Freeway) to the east in the 1940s. In 2013, a section of SR 82 was relinquished and given to the city of San Jose.
Monterey Road