As the peninsula's population grew in the 1890s, there was a strong demand for even more general merchandise establishments in Woodside and the neighboring towns. The Neuman brothers were among the first to take advantage of this early opportunity. The three brothers established their first store in Woodside in 1893, in a redwood grove along Woodside Road and Bear Gulch Creek. They purchased barrels of E. H. Rixford's La Questa Cabernet Sauvignon wine, which they sold for 16 cents a gallon.

Then there's the 1906 San Francisco earthquake, which devastated Northern California's coast along the San Andreas Fault, which runs through the Santa Cruz Mountains. Because so many of the buildings in Woodside were made of wood, they flexed with the shaking ground, preventing total collapse on the occupants and allowing them to escape. The first Neuman Bros. store was demolished, but no one was killed in the town.

The Neuman Brothers Store #2 opened a year later in 1907, located on the south side of Mountain Home Road. The building was later replaced by the original fire station for Woodside Fire District 1.

James Neuman, who was an engineer for San Mateo County, helped survey the layout for Woodside opened Store #3 in 1908. During this time, the town of Woodside began to witness the transition from horse-and-carriage to motorized vehicles.

The 18th Amendment to the United States Constitution wiped out the commercially produced wines and wineries in Woodside and neighboring towns. When the Neuman Brothers built Store #4 in the 1930s, the present location of Roberts Market, the town was dry. It wouldn't be until 1938 that La Questa Cabernet Sauvignon was back on the shelves for only a short time. Unfortunately, this would be the last vintage of the world-famous Cabernet Sauvignon produced by the Rixford family.

In 1950, Emott Caldwell bought out the Neuman Brothers and their location on Cañada Road in Woodside and renamed it Caldwell General Store.