In August 1840, the Governor of Spanish California granted the land, later called Rancho Canada de Raymundo, to John Coppinger, an Irishman who had become a naturalized Mexican citizen. This 12,545-acre rancho contained the 973 acres, which are now Huddart Park.

In 1850, the California Gold Rush was booming, and the demand for lumber to build San Francisco resulted in extensive logging operations in the rancho area. Near the present borders of the parks, 5 sawmills operated between 1853 and 1860. Richard's sawmill, built in 1853, operated just outside the present park boundary west of Skyline Boulevard. From this mill, Richard's Road led down the mountain. Wagons loaded with lumber and drawn by teams of oxen traveled down it towards Redwood City, where the lumber was barged to San Francisco. Today, Richard's Road Trail follows the route of this old road.

Near the park is the historic Woodside Store built in 1853 by Dr. Orville Tripp. Tripp's store was at the hub of activity during this early logging boom since about 15 sawmills were within five miles of its door.

James Huddart was a wealthy San Francisco lumberman and long-time resident of Woodside. He was raised in an orphanage with his sister and apparently spent a rather miserable youth. It was his desire to do something with his holdings in San Mateo County, particularly for the youth in the area.

Before his death on in 1935, Huddart deeded 900 acres of his property to the County of San Francisco with the provision that it would be accepted and developed into a public park. Due to water rights problems along Squealer Gulch Creek, San Francisco held it only two years. When the State of California also had problems with the water rights, the property was willed to the County of San Mateo, who has owned and operated the land as a public park since 1944.

In the hundred years since the Huddart Park area was logged, a new forest of redwoods and other trees have grown, covering much of the evidence of this early logging activity. However, still visible are large stumps of the virgin redwoods and "skid roads" over with the teams of oxen dragged logs to the sawmills.