Hillsborough, CA Area Guide

Hillsborough's story begins with the former Rancho San Mateo land grant and a vision of permanent residential calm. William Davis Merry Howard, whose family came from Hillsborough, New Hampshire, purchased the land in 1846, and the town that grew around it took his hometown's name. On May 5, 1910, residents voted to incorporate.

That decision gave rise to some remarkable architecture. The Carolands Chateau stands as a Gilded Age estate with Beaux-Arts details including Mansard rooflines, grand entrances, and bas-relief panels. The Tobin Clark Tudor mansion, built in 1931, anchors its own neighborhood on the eastern edge of town. Equally memorable is the Flintstone House, a cartoonish dome structure visible from Interstate 280 that has become one of the most recognizable roadside landmarks on the Peninsula.

Dining around Hillsborough means crossing into Burlingame or San Mateo, where the options are genuinely strong. Burlingame Avenue has earned a reputation as the Peninsula's go-to dining corridor, with a broad range of restaurants and a Thursday and weekend farmers market. RASA, an Indian restaurant in Burlingame, and Pausa Bar & Cookery, an Italian spot in San Mateo, have both earned recognition in the Michelin Guide.

Downtown San Mateo extends the options further, including Japanese, Taiwanese, and Mongolian cuisines -- including sushi restaurants, bubble tea shops, and Mongolian hot pot destinations.

Getting around means relying primarily on a car. Interstate 280 runs along the western edge of town and connects directly to San Francisco, about 20 miles north, and to Palo Alto and San Jose to the south. San Francisco International Airport is just six miles from town, reachable in roughly 15 minutes.

For rail commuters, several Caltrain stations are within a short drive, including Burlingame Station about seven minutes away and San Mateo Station roughly nine minutes out. BART is accessible at the Millbrae station, approximately 11 minutes by car, where it connects with the Caltrain platform. SamTrans bus service provides a limited number of stops within the town itself.

Crystal Springs Trail and the Sawyer Camp Trailhead sit on the southwest edge of town, giving hikers access to the expansive Crystal Springs Reservoir area with open views across the Peninsula foothills. The Crystal Springs Golf Course weaves through that same natural landscape and is open to the public.

In central Hillsborough, the Burlingame Country Club, established in 1893, operates a private 18-hole golf course with views of San Francisco Bay. A short drive east, San Mateo Central Park covers 16 acres and includes a mini train ride, playground, and ice-skating rink. The Japanese Tea Garden and San Mateo Arboretum are both within nine minutes of town, and Bayside Park offers waterfront access along the bay.

Very little retail exists within Hillsborough's borders, so Burlingame and San Mateo handle all shopping needs. Burlingame Avenue serves as the area's main retail corridor, lined with shops, jewelry stores, coffee spots, and grocery options. A farmers market runs on Thursdays and weekends and draws steady crowds.

San Mateo's downtown adds broader variety, and practical shopping centers including Safeway Center and The Landmark are reachable within six to seven minutes by car -- keeping everyday errands close even without anything commercial inside town limits.

A rare residential town with landmark estates like the Carolands Chateau and the iconic Flintstone House, Hillsborough pairs quiet hillside streets with easy access to Crystal Springs trails, Peninsula golf, and San Francisco International Airport just six miles away.