In 1776, after much preliminary exploration along the Peninsula, mission outposts were established at the northern tip of the Peninsula (Mission Dolores) and at the southern end of the Peninsula (Mission Santa Clara).
In theory, the distance between these two missions was within a hard day’s walk if the trip was begun really, really early in the morning. There were many obstacles to be overcome in the 1700s, however, before this path was safe and easy to travel. Fields of grasses, meadows, sand, solid and loose dirt, gumbo-like mud, deep creeks, and stands of willows had to be traversed to reach the missions in either direction.
The easiest path, along the foothills in many places, became well-worn over the initial years of exploration and establishing the missions. Crude bridges, mainly of logs, were built to span the troublesome creeks that were sometimes deep and difficult to negotiate, especially during the rainy season.
These numerous creeks that flowed out of the steep watershed hills to the west of the paths presented the greatest challenges to the traveler. As wagons and later stagecoaches became more common, they would require a lot of care and effort to negotiate the creeks when bridges washed out or were damaged by use.
Travelers spent a long time getting around the barriers and, over the years, these barriers to travel fostered rest stops that sometimes developed into roadhouses, such as Uncle Tom’s Cabin (the 14-mile house) that served the public for a hundred years.
Because of these land obstacles on the Peninsula, travel remained slow, and isolation of the travelers was the norm. However, in the autumn of 1849, with the impetus of the gold rush, an attempt was made to make the trip from San Francisco to Santa Clara faster and easier when John W. Whistman began a stage line.
The trip started at Portsmouth Square in San Francisco with an old French omnibus and a few mustangs and mules, and ended in San Jose. The trip was neither easy nor inexpensive. The cost was usually two ounces of gold dust — which was about $32. It took nine grueling hours of rough riding by the passengers as they were jostled over the rutted roads. In the winter the trip was even worse as the horses and coach had to contend with a road that had now been turned into a brown mass of mud.
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The gumbo stuck to everything — the horses’ feet, the wheels, boots, and clothes — and removal was impossible until the stagecoach had reached its destination. But other stagecoach owners were undeterred and by July 1851, the stage coach was extended to Monterey.
In the early 1860s the San Francisco and San Jose railroad was built and changed the transportation picture completely. No longer did the passengers have to contend directly with the elements, as they rode in comfortable cars that no longer were at the mercy of an uneven roadbed.
The rails were straighter and surer than the well-worn path that had led down the Peninsula since the 1770s. Schedules were set and did not vary due to bridge conditions or mud. Although the railroad was a vast improvement for travel up and down the Peninsula, its rails were set and did not venture to the coastside or the hills where goods, mail and other services were needed.
Crystal Springs Road in San Mateo was the route John G. Moore followed in 1860 when he began his stagecoach route to Pescadero on the coast. This was a very rough and strenuous trip for the horses as the roads were even less improved through the hills to the west. In 1869 a much improved toll road, the San Mateo/Half Moon Bay Toll Road, was built and this eased the trip considerably.
The lumbering communities of Woodside and Searsville were jubilant when, in 1864, Mr. Blanchard began running a stage from Redwood City to their areas carrying mail and passengers. His stage left Redwood City after the train arrived from San Francisco with the mail, and the day-long circular trip met the trail again in Redwood City in the afternoon. S. L. Knight bought the line in 1865 or ’66 and the stage continued service to Searsville and Woodside until 1872 when the route was extended to San Gregorio after the Redwood City and San Gregorio Turnpike was formed. Later it was extended down to Pescadero and operated daily, weather permitting, until about 1910.
The stagecoach trips were extremely important to the travelers for maintaining contact with the isolated farms and businessmen along the coast, although the stagecoach did not serve the one function many along the coast wanted — a way to get their products to the market.
This problem was solved in 1907 when the Ocean Shore Railroad began operations along the coast. It also rang the death-knell for the stagecoaches, although it wasn’t until 1910 that the last stagecoach ceased operation to Pescadero. By 1913, all stagecoach activity had ceased and a romantic era faded into memory.

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