In 1865, a franchise was issued to build a toll road from San Mateo to Half Moon Bay.
Construction costs were not to exceed $20,000. It was to connect with the route that led to San Mateo Creek and up to the Crystal Springs Valley where the San Mateo Creek entered Crystal Springs Valley. The road was hacked out alongside of the creek and then turned to the south in Crystal Springs Valley before it turned west again and climbed to the spine of the northern Santa Cruz Mountains. Following Indian and Spanish trails that had been established over the years, the construction up the east side of the mountain was steep, but relatively easy compared to the sheer drop-off that was encountered on the west side of the mountain. The west side had to be negotiated by a great number of switchbacks. The vegetation that consisted of chaparral had to be hacked down to facilitate the twisting road. The road as it continued west entered a small pleasant valley. From this point the valley was narrow, but with a flat bottom that allowed fairly easy construction in the town of Half Moon Bay.
The road was called San Mateo Road, and the main transportation along this road was the stagecoach that ran from the railroad station in San Mateo to the Occidental Hotel in Half Moon Bay. It was a two-hour ride one-way for the passengers. There was another small hotel in the Crystal Springs Valley by the confluence of the San Mateo Creek. This was later flooded when the Crystal Springs Dam was constructed between 1887 and 1890.
In 1879, the county constructed a road over Montara Mountain. This road was called the Half Moon Bay-Colma Road. It solved the transportation problem Half Moon Bay had getting their produce to the San Francisco Market, but over time it proved to be inadequate as well as too dangerous, and it was closed in 1915. Meantime, another form of transportation was tried — a railroad along the coast. The San Mateo toll road did not produce enough revenue for its investors, and the county bought it for $7,500 in 1881.
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In the 1910s, the coastside was still plagued by inadequate roads and the county began a road along the northern portion of the Santa Cruz Mountains by creating Skyline Boulevard. At the same time, the coast was blessed by another attempt for better roads with the building of the Coastside Boulevard. On Oct. 31, 1915 thousands drove over Montara Mountain, honking their horns at every one of the 250 curves of the road. Skyline Boulevard construction did not progress as fast as the coastside route.
At this point, San Mateo and other Bay cities were expanding and business opportunities abounded. In 1923, the pressure to build a bridge across the Bay to Hayward resulted in the San Mateo/ Hayward Bridge being erected in the late 1920s. However, the bridge exited into San Mateo at Third Avenue and the road essentially stopped at the newly developed Bayshore Highway. The route to Half Moon Bay out of San Mateo remained along the San Mateo Creek to Skyline Boulevard. Half Moon Bay was being left out of business opportunities and access to the Bay due to lack of a good, straight road to the Bay.
The state of California bought the San Mateo-Hayward Bridge in 1951. That year, there was an average of 5,200 cars using the bridge every day. In 1955, the average rose to 9,000 cars a day. In the early 1960s, Foster City was to be constructed and the highway from the bridge was to be extended across the old Brewer Island Dairy to Bayshore, then continue to the west to hook up with the San Mateo Road to Half Moon Bay. Construction of a new bridge and the realigned highway began in 1961 at a cost of $70 million. In 1966, 5,000,000 cars crossed the old bridge. On Oct. 20, 1967, the new bridge opened and 9,100,000 vehicles crossed the following year.
The highway across the San Mateo-Hayward Bridge, as well as the extension from the Bayshore, through San Mateo’s western section, to Half Moon Bay was now connected and given the designation of State Route 92. Most people have forgotten that the section from Skyline Boulevard to Half Moon Bay was designated as San Mateo Road.

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