In the area that now stretches from South San Francisco to Belmont, the Ohlone tribe flourished, fished and crafted canoes from reeds along the Bay for nearly 4,000 years before a group of Spanish explorers made camp there for the first time. In 1776, thirteen Spanish soldiers and a priest on a scouting trip, set up camp near a stream they named San Mateo Creek. 20 years later, a Spanish mission in San Francisco built an outpost on the stream to expand the reach of the church and oversee converts. It was the first building constructed in the territory that would later become the city of San Mateo.

In 1822, Mexico won independence from Spain, which led to the missions being secularized open to free trade. The Mexican governor some thirteen years later granted massive tracts of land to a few residents and associates. One of the grants was called Rancho San Mateo and it was so large (nearly 6,500 acres) that it would one day comprise parts of modern day San Mateo, northern Burlingame and all of Hillsborough.

The owner of Rancho San Mateo was east coast merchant, William Davis Merry Howard, who purchased it for $4 an acre and built the first great estate in the area, called El Cerrito. At the same time, the abandoned mission outpost was converted into a stagecoach stop, which established the main street of the town that would follow later. 

Howard’s mercantile business in San Francisco and the whole Bay Area experienced a boom following the gold rush. San Francisco businessmen wanted country and weekend homes outside the city. After train stations were built in San Mateo and two of its neighboring cities in the second half of the 1800s, these idyllic towns could be reached from San Francisco in a little more than half an hour. They became popular destinations for wealthy San Franciscans due to their mild mediterranean weather, rolling green hills and genteel society. Some of the most powerful figures in the West built Peninsula estates in the middle of the 19th century, creating a culture of luxury and serenity that exists still today.

Several, almost simultaneous, events changed the town starting in 1889. The Crystal Springs dam was completed, the first newspaper was established and the Howard estate began to subdivide and sell parcels of land. Within five years, the city of San Mateo was officially incorporated.

Today, San Mateo has a population of around 104,000 and covers roughly 16 square miles. The city varies from urban neighborhoods to oak woodlands to bayland marshes. It is home to Sony Interactive Entertainment and giant tech headquarters such as Roblox, Go-Pro and YouTube.

San Mateo hosts a community college, Japanese Tea Gardens, a network of bikeways, a zoo, a hands-on science museum and a 670 acre park on the coast, called Coyote Point Park, where locals go to windsurf and sail.

The downtown is crossed by a freshwater creek and many of the 800 shops and restaurants in are located in historic buildings dating back to the late 1880’s, which adds a unique sense of history and charm to the largest downtown in all the San Francisco Peninsula.