With just some 16 square kilometers of territory, Hillsborough, California, is nearly a 100% residential city of San Mateo County.
It has no commercial zone; thus, this city offers no tourism infrastructure, restaurants, or accommodations for its visitors.
Nonetheless, Hillsborough offers some charming attractions, primarily its historic homes that offer windows to the city’s past.
Hillsborough’s rise as a prime and exclusive residential community started in 1846 when a wealthy shipping magnate from Hillsborough, New Hampshire, relocated his family in this San Francisco Bay area.
Other wealthy families from San Francisco soon followed, and thus began Hillsborough’s development into one of the richest US residential enclaves.
A visit to Hillsborough offers a peek at the premier points of interest not only within the city but its neighboring urban centers.
Check our list below to explore some of these destinations and the best things to do in and around Hillsborough.
Reserve a Tour of Carolands
Catch a glimpse of how the rich and famous of the past lived, with a tour of the magnificent mansion Carolands at 565 Remillard Road.
The heiress to the Pullman railroad car company, Harriet Pullman Carolan, had this opulent residence built in 1915-16.
Carolands has a floor area of about 65,000 square feet, and it rose as the centerpiece for a 500-acre estate.
Also called "The Chateau," this mansion is striking for its French Classical architecture, standing impressive amid lush and verdant landscaping.
Carolands’ design was inspired by the famous Vaux le Vicomte in France, a prototype for the Palace of Versailles.
Carolands is one of the largest residences in the US and is registered in the National Register of Historic Places.
Spend a Quiet Day at Vista Park
Drop by Hillborough’s Vista Park at 1030 Vista Road to appreciate up close its complete renovation.
This park, wedged between the streets of Culebra and Chiltern, is on the embrace of lush trees canopies and verdant vegetation.
The facilities here include picnic tables, a football ground, and a basketball court, and separate play facilities for kids.
Accessible to wheelchair-bound visitors, the park provides an area with rubberized surfacing, and its large playing field comes with a clamshell backstop.
As a special feature, the park flaunts a large compass as its centerpiece to indicate Hillsborough's distance from other city landmarks around the world.
Take a Peek at the Flintstone House
See one of the most photographed houses in the San Francisco Bay Area—the “Flintstone House.”
This residence presents a structure recalling vividly the Stone Age dwelling in the popular animated cartoon series The Flintstones.
Located at 45 Berryessa Way, this unique house can be seen to the east from the Doran Memorial Bridge.
Locals also call it the Bubble House, the Dome House, the Worm Casting House, and the Gumby House, but seeing it, you’re more likely to yell, “Yabba dabba doo!”
Noted LA architect William Nicholson designed the Flintstone House, which was built around 1976.
He used an unorthodox construction technique in this project, spraying concrete over balloon-shaped wire foundations to achieve that Flintstone House look.
Stroll at Centennial Park and the Town Hall
Visit the Hillsborough Centennial Park at the corner of El Camino Real and Floribunda Avenue on the grounds of the city’s town hall.
Renovated in 2009, this park was built in 1989 and was formerly known as the Hillsborough Water Conservation Park.
One of this park’s main purposes was to show the residents of Hillsborough and neighboring communities various water conservation techniques and their benefits.
The park is home to native plants, which are drought-resistant, and thus need low-water maintenance.
The Centennial Park also displays an automatic drip irrigation system to maintain its charming garden.
After your park visit, you can drop by the town hall to check out the fun activities on the calendar of the Hillsborough Recreation Department.
Go for a Green Thumb at Hillsborough Harvest Garden
Check out the plots at The Hillsborough Harvest Garden at 660 Fairway Circle, where plants successfully grow in Hillsborough’s microclimate.
In this garden, you can catch two-hour seasonal workshops on horticulture.
These educational sessions are held every other Sunday from March to November.
The things you can learn here include preparing and improving the soil for planting, tools maintenance, and pest management.
Other techniques that the Hillsborough Harvest Garden shares are pruning fruit trees in summer and winter, sowing seeds, and transplanting.
This garden is one of the projects of the non-profit Hillsborough Beautification Foundation that you can also visit at the city’s town hall at Floribunda Avenue.
Other Things to Do Nearby
Explore the Sawyer Camp Trail
Head to the south entrance to the Sawyer Camp Trail in San Mateo, which is just off the western flank of Hillsborough.
Sawyer Camp Trail is an asphalt-paved, 18.2-kilometer pathway that is accessible all year-round.
It is a segment of the Crystal Springs Regional Trail running through the San Andreas Fault rift valley in San Mateo County.
This trail traverses through the area near Crystal Springs Dam and heads north along the Crystal Springs Reservoir.
It follows along the shoreline of Lower Crystal Springs Reservoir and reaches up to San Andreas Lake.
Along the trail, you'll pass by the 600+-year-old Jepson Laurel tree, the oldest tree of its kind in California.
You will have access to restrooms and a picnic area along the trail, but be sure to bring your own water.
Book a Tee Time at Crystal Springs Golf Course
Enjoy the panoramic views of Crystal Springs Reservoir while hunting for pars and birdies at the Crystal Springs Golf Course in Burlingame.
Its links are located less than 4 miles south of Hillsborough and host a wildlife refuge spread over 32,000 acres.
This 18-hole championship golf course plays at par 72 over 6,515 yards from its farthest tees.
The course’s layout follows the natural contours of the San Francisco Valley, providing a challenge to golfers of all skills and abilities.
Post-game, you can enjoy the offerings at the golf course’s 19th Hole Pub & Grill, including hotdogs, hamburgers, and club sandwiches.
Seek the Seclusion of Aardvark Beach
Proceed to Aardvark Beach at 193 Airport Blvd., Burlingame, if you want to avoid the beach fees at the Coyote Point Recreation Area.
Aardvark Beach, too, is less than 4 miles to the east of Hillsborough, and here, you will be rewarded with a secluded stretch of the San Francisco Bay.
The near-shore waters of this beach feel decently warm, so you can enjoy relatively quiet and undisturbed swimming.
Free parking on the roadside is likewise available on this smart alternative in a Hillsborough holiday.
Enjoy Bayside Park of Burlingame
Capture more of the best views of San Francisco Bay while enjoying an outdoor vibe at Bayside Park.
Located at 1125 Airport Blvd. in Burlingame, this park is less than 3 miles northeast of Hillsborough.
Besides its two baseball fields and a soccer field, this popular bayside facility also has a dog exercise park.
Bayside Park also provides hiking trails that offer you the option for a leisurely walk along the scenic San Francisco Bay’s coastline.
All told, this park is a great place for relaxation and to experience the wholesome California weather that this bayside region offers.
Take the Kids to the Coyote Point Recreational Area
Go on a kid-friendly adventure at the Coyote Point Recreational Area in San Mateo, just 4 miles northeast of Hillsborough.
This family destination offers a wide selection of recreational activities, such as swimming, boating, sailing, fishing, and windsurfing.
Coyote Point is also ideal for picnics, biking, jogging, as well as golfing in its nearby Poplar Creek Golf Course.
The Magic Mountain Playground in Coyote point will likewise appeal to your kids with its giant, castle-and-dragon theme.
They can also get acquainted safely with wild animals and enjoy the interactive science exhibits at Coyote Point’s CuriOdyssey.
Shop for Health at the Burlingame Fresh Market
Visit Park Road in Burlingame for healthy food items sold at the Fresh Market, less than 3 miles east of Hillsborough.
Bay Area residents troop to this market where California farmers sell their fresh produce either Sunday mornings or Thursday afternoon from April to December.
This hub of healthy, organic food items is one of the few farmers’ markets regularly operating in the Bay Area.
Many local retailers also take advantage of the free booth space in this market to sell processed foods manufactured locally.
Family-oriented entertainment, music, artisans, and other community come-ons are also part of the scene in this Fresh Market operated by the Burlingame Chamber of Commerce.
Meet the Creatives at the Peninsula Museum of Art
Seek the Peninsula Museum of Art at the Shops at Tanforan in San Bruno, which is less than 7 miles north of Hillsborough.
This mall at 1150 El Camino Real is the new home of this museum, which features several artists’ studios and galleries.
Since 2003, this museum has been promoting personal interactions between professional artists and the community.
The Peninsula Museum of Art holds rotating exhibits, so each of your visits to its galleries promises something new.
Besides these exhibits, the museum also hosts art workshops and seminars both for kids and adults.
Thankfully, admission is free to all of the events that the Peninsula Museum of Art holds.
Shop at the Burlingame Downtown
Head east from Hillsborough to the Burlingame Downtown District for some great shopping.
This commercial area, just 2 miles from Hillsborough, is located along the flanks of Burlingame Avenue.
Along this corridor are hundreds of retail stores, restaurants, and service providers, with each nook offering surprises.
Along Broadway Street, between El Camino Real and California Drive, prized finds are waiting in its 50s-style shops and restaurants.
Right next to the downtown district, you can switch to the Fox Mall Shopping Center off El Camino Real between Howard and Burlingame Avenue.
Your picks in this mall include Fox Mall Fine Jewelry & Gifts, Shoe Doctor & Irene’s Alterations, Safeway Food and Drug, Walgreens, Great Clips, and Yogurtland.
Pamper Your Sweet Tooth at Preston's Candy & Ice Cream
Take the whole family for sweet treats at Preston’s Candy & Ice Cream at 170 Broadway, Burlingame, only less than 2 miles northeast of Hillsborough.
Notably, this destination predates the 1971 hit fantasy film Willy Wonka & the Chocolate Factory.
For over 60 years, the family-owned Preston’s Candy & Ice Cream has been manufacturing and selling ice cream and candy products in Burlingame.
This quaint factory makes small batches of candy every day in its kitchen to guarantee high product quality and freshness.
Visit Preston’s in the morning for a chance at joining a behind-the-scenes tour of its kitchen.
During this tour, you can enjoy chocolate tasting for an experience best shared with the entire family.
Dine Gaucho-Style at the Espetus Churrascaria
Experience servings of authentic Brazilian steak at the Espetus Churrascaria at 710 South B Street, San Mateo, only 4 miles east of Hillsborough.
A native gaucho or South American cowboy conceptualized this restaurant that opened first in San Francisco and followed it up with a branch in San Mateo.
Espetus Churrascaria today prides itself as the No. 1 Brazilian steakhouse in the Bay Area.
At this restaurant, waiters in Brazilian gaucho costume serve eat-all-you-can skewers of meat amidst a fabulous setting.
The Gaúcho chefs ensure the authentic texture and flavor of the steak with their slow grilling of the skewered choice meat cuts over an open flame.
The chefs themselves carve and offer the steak tableside to the customers and will stop only when you’re fully content.
The points of interest within Hillsborough for casual visitors are understandably fewer, as this city is primarily a residential domain for well-to-do families in the San Francisco Bay area.
Be that as it may, Hillsborough provides enough destinations and activities to leave a lasting impression to anyone visiting its area and neighboring communities.