Arthur and Mona Hofmann House

Hillsborough is an incorporated town in San Mateo County, California, in the San Francisco Bay Area. It is located 17 miles (27 km) south of San Francisco on the San Francisco Peninsula, bordered by Burlingame to the north, San Mateo to the east, Highlands-Baywood Park to the south, and Interstate 280 to the west. The population was 11,387 as of 2020.

Crystal Springs Uplands School is an independent, coeducational, college prep day school in Hillsborough, California, United States. Founded in 1952, the school includes grades 6-12, with approximately 220 students in the middle school and 320 students in the upper school. In late 2007, The Wall Street Journal identified Crystal Springs Uplands School as one of the world's top 50 schools for its success in preparing students to enter top American universities.

Odyssey School is a private middle school in San Mateo, California, a town about 15 miles (24 km) south of San Francisco. Odyssey caters to students in grades 6 through 8. Its five academic core subjects consist of writing, mathematics, science, humanities, and Japanese. Offerings in creative arts include drama, choir, music history, pottery, set design, costume design, and photography. The school also teaches swimming, dance, karate, and stage combat under its movement program.Odyssey's theater program includes visits to the Oregon Shakespeare Festival in Ashland, Oregon, where students see and study a cross-section of Shakespeare's plays. The school's Japanese program includes hosting Japanese exchange students each autumn, followed by a three-week trip to Japan at the end of eighth grade, in which students stay at temples and Japanese homes.Odyssey students have won a variety of prizes in outside academic competitions. These include a first place in Notre Dame High School's 2009 Middle Math Contest (out of 190 contestants), and a first place in the 2008 Japanese speech contest of the Japanese Consulate General. Odyssey's programs for helping students cope with stress have attracted regional attention.Many Odyssey graduates attend college-preparatory schools such as San Francisco University High School, Woodside Priory School, Crystal Springs Uplands School, and Menlo School. Others go on to local public high schools. Odyssey graduates later continue their studies at four-year colleges and universities such as UC-Berkeley, Cornell, Occidental, Reed, and Carnegie Mellon.Odyssey was founded in 1998.Odyssey's founding Head of School, Stephen K. Smuin, has been a teacher and school administrator for many years. He had been head of the middle school at the Nueva School, a private elementary and middle school in Hillsborough, California, but was ousted by the school board following allegations of abusive behavior towards a former student. He is the author of three books on writing technique, including "More than Metaphors: Strategies for Teaching Process Writing.". He retired in June 2010. In July 2010, Daniel Popplewell joined Odyssey as its new Head of School. He had been dean of teaching and learning at Bentley School in Lafayette, California. He was succeeded in July 2013 by Stephen P. Lane, who had been head of Santa Barbara Middle School.

College of San Mateo (CSM) is a public community college in San Mateo, California. It is part of the San Mateo County Community College District. College of San Mateo is located at the northern corridor of Silicon Valley and situated on a 153-acre site in the San Mateo hills. The campus was designed by architect John Carl Warnecke. The college currently serves approximately 10,000 day, evening and weekend students. The college offers 79 A.A./A.S. degree majors, 75 certificate programs and approximately 100 transfer areas and majors.

Carolands Chateau is a 46,050-square-foot (4,278 m2), 4.5 floor, 98 room mansion on 5.83 acres (2.36 ha) in Hillsborough, California. An example of American Renaissance and Beaux-Arts design, the building is a California Historical Landmark and is listed on the National Register of Historic Places. Carolands is one of the last of the houses built during the Gilded Age, a period of great mansion-building that included famous houses of the Vanderbilt family, such as Marble House, Biltmore Estate and The Breakers, and stately California houses such as Filoli and the Huntington family's mansions.

The Flintstone House is a free-form, single-family residence in Hillsborough, California overlooking and easily seen from the Doran Memorial Bridge carrying Interstate 280 over San Mateo Creek.

Aragon High School is a public co-educational high school in San Mateo, California. It is part of the San Mateo Union High School District (SMUHSD). It is located in San Mateo County, a large suburb just outside San Francisco. The school is accredited by the Western Association of Schools and Colleges (WASC).

The Bridge School is a non-profit organization in Hillsborough, California for children with severe speech and physical impairments. It aims to allow the children to achieve full participation in their communities through Augmentative and Alternative Communication (AAC) and Assistive Technologies (AT). The school was founded by Pegi Young, Jim Forderer and Dr. Marilyn Buzolich in 1986, and has since become a world recognized leader in AAC and AT.

The Doran Memorial Bridge is the twin pair of steel girder bridges that carry eight lanes of road traffic on Interstate 280 over San Mateo Creek near Hillsborough, California in San Mateo County.

The San Mateo County Community College District is a community college system in California with three institutions: College of San Mateo in San Mateo, Cañada College in Redwood City, and Skyline College in San Bruno. The district serves more than 25,000 students each day with both day and evening classes.

Crystal Springs Dam is a gravity dam constructed across the San Mateo Creek which is in San Mateo County, California. It impounds water to form the Lower Crystal Springs Reservoir which sits atop the San Andreas Fault in a rift valley created by the fault. The dam itself is located about 300 yards (273 meters) east of the fault. It was among the first concrete gravity dams built in the western United States. Skyline Boulevard runs over the dam, which also forms the trailhead of the popular Sawyer Camp Trail.

Crystal Springs Regional Trail is a county park located between San Bruno to the north and Woodside to the south. The park comprises three main trails: Crystal Springs Trail on the south, Sawyer Camp Trail in the middle, and San Andreas Trail in the northern section, which run along the eastern shore of San Andreas Lake in San Mateo County. Settled thousands of years ago by the Shalshone Indians, the Crystal Springs Reservoir (separate from San Andreas Lake to the north) is currently part of the City of San Francisco's Hetch Hetchy Reservoir water system. Crystal Springs reservoir is long and narrow because it lies atop the San Andreas Fault. The famous fault runs right through the Crystal Springs Reservoir. Satellite images and maps show the long narrow San Andreas rift continuing north of San Francisco in Tomales Bay, in Point Reyes National Seashore in a straight line. The Crystal Springs Dam survived both the 1906 earthquake and the 1989 Loma Prieta quake with no damage whatsoever, according to the U.S. Geological Survey.