The earliest historical trail remnant of Montara Mountain is the precolonial Indian Trail which traverses the ridgeline between Willow Brook Estates towards Saddle Pass following the high ridgeline above Green Valley and winding down towards Martini Creek. Remnants of this trail remain visible today.
Colonial history The earliest descriptions of the area are from the
Portolá Expedition in 1769, "We halted near the shore, along which the passage was entirely closed by a steep hill, at the foot of which ran a stream of good water. This stream flowed from a hollow formed by various hills; at the extreme end of this hollow, close to the hills, we pitched our camp, which was thus protected to the north. To-day’s march was one league. The place afterwards known by the name of Rincón de las Almejas." On October 31, the expedition began its climb of Montara Mountain. Portolá wrote: "We travelled two hours of very bad road up over a very high mountain." When they got to the top, the commander noted that "25 heathens came up." These were the
Aramai of
Pruristac. "A village of very fine, well-behaved friendly heathens, …(who brought) a good many black pies made of seeds...There must be many villages...for we have seen many smokes from here; mussels are also very plentiful here, and very large... Many deer have been seen upon the hills here... Bear tracks and droppings have been seen...our sick men since we left the creek of La Salud (Waddell Creek in Santa Cruz County) have been improving more every day..." They had descended the treeless hill and pitched camp in the middle of a small valley (San Pedro).
Mexican period During the Mexican Rancho era, a road known as
Camino Pedro Cuesta also traversed Saddle Pass and connected the
Sanchez Adobe in
Rancho San Pedro in San Pedro Valley with
Rancho Corral de Tierra Palomares in Montara. Following the Mexican–American War of 1848, this routing was known as "Road Trail" and was considered to be nearly impassable to wheeled vehicles. In 1879 this steep and rutted Road Trail crossing of Montara Mountain was replaced by the marginally improved road known as the Half Moon Bay - Colma Road, which included road grades of 24%. This road which routed closer to the ocean and
Devil's Slide terminated in Shamrock Ranch and persisted until 1915. ==Biodiversity==