[11] Captain Frederick William Beechey in 1827 traveling with the hills on their right, known in that part as the Sierra del Sur, began to approach the road, which passing over a small eminence, opened out upon "a wide country of meadow land, with clusters of fine oak free from underwood...

It strongly resembled a nobleman's park: herds of cattle and horses were grazing upon the rich pasture, and numerous fallow‑deer, startled at the approach of strangers, bounded off to seek protection among the hills...

[12]: 32  William Davis Merry Howard purchased Rancho San Mateo from Arenas[13]: 93  in 1846 for US$25,000 (equivalent to $848,000 in 2023) and spent an equal sum erecting a fence around the property.

[12]: 44 In the 1850s, following the American Conquest of California, many San Franciscans began building summer homes in the mid-Peninsula, because of the milder climate.

[14] The area that is now the city of San Mateo was owned by a few large landowners, including Howard, whose Rancho San Mateo occupied 6,438 acres (2,605 ha) in 1853[13]: 93 [15] north of San Mateo Creek,[16]: 92  pushing most of this early settlement into adjacent Hillsborough, Burlingame, and Belmont; other significant landowners in the area included John Parrott, who purchased 500 acres (200 ha) in 1860[12]: 51  south of the creek and southwest of El Camino Real and Alvinza Hayward, who owned the land south of the creek and east of El Camino.

[19] The Howard Estate was built in 1859 on the hill accessed by Crystal Springs Road; the building, named El Cerrito, eventually was moved to Hillsborough and served as its Town Hall starting from in 1910, but it has since been demolished.

[citation needed] Hayward Park, the 1880 American Queen Anne-style residence of Alvinza Hayward (often said to be "California's first millionaire" from his silver and banking fortunes), was built on an 800-acre (3.2 km2) estate in San Mateo which included a deer park and racetrack, roughly bounded by present-day El Camino Real (on the west), 9th Avenue (on the north), B Street (on the east) and 16th Avenue (on the south).

[citation needed] Although Joseph (José) Evencio (the younger) was reported to be his descendant living at Coyote Point until World War II, "Indian Joe", (Joe Mestes) was the American Indian who was actually hired by the Howard family to oversee their land holding at Coyote Point.

His final whereabouts were reported to be a care facility in Oakland after he had been removed from Coyote Point when a Merchant Marine Academy was established there.

[23][24] In the early 20th century, Japanese immigrants came to San Mateo to work in the salt ponds and flower industry.

Although Japanese-Americans only account for 2.2% of the population today, they continue to be a major cultural influence and a draw for the rest of the region.

[30][31] Linda would travel to Vietnam to meet with the men of Alpha Company for Christmas in 1968 and deliver personalized medallions from the City of San Mateo.

[27] In 1988, Joseph Brazan wrote a screenplay entitled A Dove Among Eagles chronicling the adoption of Alpha Company by San Mateo and the real-life romance between Linda and Artavia's commander, Lt. Stephen Patterson.

The best-known natural area is Coyote Point Park, a rock outcropped peninsula that juts out into the San Francisco Bay.

The variety of natural habitats includes mixed oak woodland, riparian zones, and bayland marshes.

One endangered species, the California clapper rail, was sighted feeding on mudflats by the Third Avenue bridge in San Mateo.

[40] In the late 20th century, this mixed oak woodland and chaparral habitat was a site of controversy related to proposals to develop a portion of the mountain for residential use.

Sawyer Camp Trail, located on the western edge of San Mateo along the Crystal Springs Reservoir, is another popular destination for joggers, pedestrians, and bikers.

[41] Central Park is considered to be San Mateo's signature park with a baseball field, tennis courts, sculptures, picnic areas, playground, Japanese tea garden, recreation center, miniature train, rose garden and the San Mateo Arboretum.

Segments of South B Street between 1st and 3rd Ave. and the southbound lane between Baldwin and 1st Ave. were temporarily closed to vehicular traffic in 2020 to allow for expanded outdoor dining.

[43] The San Mateo City Council extended the temporary closure through the end of 2021 and voted in September 2021 to create a permanent pedestrian mall between 1st and 3rd Ave.[44] The plan requires a 12-foot (3.7 m) fire lane in the center of the street for public safety vehicles and necessary garbage or delivery services.

The city aims to conduct the project in two phases: First, by installing retractable bollards and updating traffic signals and signage, then by raising the level of the street to be flush with sidewalk and reimagining its landscaping.

[48] New entertainment additions include luxury movie theater Cinépolis and a Pinstripes bowling alley off El Camino Real.

Hispanic or Latino people of any race were 25,815 (26.6%); 14.4% of San Mateo is Mexican, 2.8% Guatemalan, 2.6% Salvadoran, 1.2% Peruvian, 0.9% Nicaraguan, 0.5% Puerto Rican, 0.3% Colombian, 0.3% Chilean, 0.2% Honduran, and 0.2% Cuban.

[64] The economy of San Mateo is considered very diverse, with jobs in the technology, health care, financial services, government, and retail trade fields being among the most numerous.

[66] In the mid-2000s, the second stories of downtown San Mateo buildings became a hub for startup companies, including Roblox, GoPro and YouTube.

The campus of over 10,000 students is located on 153 acres (0.62 km2) in the western foothills of the city which offer a panoramic view of the San Francisco Bay.

[71] The newest Main Library building, at 55 West 3rd Avenue near Central Park in downtown, opened in 2006 after residents passed a $35 million bond measure; the remaining funds came from state ($20 M) and private sources ($10 M).

One of the more memorable works is the large, brightly colored 1963 mosaic mural designed by Louis Macouillard and constructed by Alfonso Pardiñas.

[85] AC Transit provides transbay bus service via the San Mateo Bridge to Alameda County.