Things to Do Around Hillsborough

Sternsmith Group


Hillsborough, California, is a beautiful town located in the San Francisco Bay Area. Residents are drawn to this quiet, residential community known for its large single-family homes on expansive lots. Hillsborough homes for sale are typically purchased by individuals and families seeking a quiet, residential community with excellent schools, and a central location between San Francisco and Silicon Valley. Hillsborough is a town, but there are no businesses allowed.  Here are some of the fun things to do in and around Hillsborough:

Crystal Springs Reservoir

The inspiration for the Hoover Dam, Crystal Springs Reservoir was built in 1888 and is a popular destination for walking, jogging, and biking with a spectacular view.

Golfing

If you’re a golf enthusiast, you can hit the links at the Crystal Springs Golf Course, which is known for its scenic setting. The course was designed by renowned British golf architect William Herbert Fowler in 1924. He focused on building the course to integrate seamlessly with the natural landscape, giving it its unique feel.

Burlingame Avenue

Just a short drive away, you can explore Burlingame Avenue. This charming shopping district has boutiques, cafes, restaurants, and more. This pedestrian friendly district is packed with big city amenities while maintaining that relaxed, small town feel. Check out our Burlingame guide for how we recommend spending your day.

Burlingame Farmers Market

The Fresh Market is held on Thursdays from 3-7pm, May through November, and Sundays 9 am to 1:30 pm all year round. This community owned and operated market is one of the few in the Bay Area and is known to have local artisans and musical entertainment alongside the California seasonal produce, flowers and local food products

Filoli Historic House and Garden

Located nearby in Woodside, Filoli is a magnificent country estate with beautiful gardens, a historic museum, and walking trails. It’s a great place to immerse yourself in nature and history. One of our family favorite events is to go see the holiday lights, drink cocoa, and enjoy the holiday cheer in December.

Coyote Point Recreation Area

Spend the day at the Coyote Point Recreational Area, which is a short ride from Hillsborough. For those under the age of 7, CurioOdyssey Kids Museum is a must see and the Magic Mountain Playground featuring a themed play structure, slides, and more, is perfect for all children. Activities for the whole family include hiking and biking the trails with scenic water views or taking everyone out for a day at the beach. Set up a picnic on the beach or take to the bay to swim, paddleboard, windsurf, kayak, canoe, or boat.
 

Spend Time in Local Hillsborough Parks

Vista Park boasts two playgrounds, one for older children and one geared toward toddlers. We love that the park is enclosed for kids under 5.  Bring your picnic blanket or enjoy one of the many tables. A walking loop, climbing rocks, a large playfield, and a basketball court round out the many features of Vista Park. If you are new to Hillsborough, Vista Park is a must to mix and mingle with other parents and caregivers and perfect to rent for events. Other notable Hillsborough parks and playgrounds include South Hillsborough Elementary playground,  West Hillsborough Elementary park, and North Hillsborough School playgrounds. Most Hillsborough homeowners with kids venture into Burlingame to enjoy Washington Park as their kids get bigger.

Carolands Mansion

If you are interested in beautiful architecture dating back to the Gilded Age, reserve a carefully curated tour of the Carolands Chateau. This mansion has ninety-eight rooms sprawled across four-and-a-half floors and over 46,000 square feet. The house was built in 1912 and underwent extensive restoration nearly thirty years ago. During the tour, your guide will address the history and architecture of the home.

Flintstone House

As you drive along on Highway 280 near Black Mountain Road, enjoy the Flintstone House in Hillsborough. While the Flintstone House is privately owned and does not offer tours, you will not want to miss taking a peek at this incredible architectural feat. One of several dome-shaped homes, the Flintstone House was constructed in 1976 by Bay-area designer William Nicholson. Its whimsical bubble-shaped architecture is now painted a brilliant orange, with one dome contrasting in a bright purple. The property has been a subject of both admiration and controversy over the years. Some locals and visitors appreciate its quirky and playful design, considering it a part of California's architectural history. However, others have criticized the house for being an eyesore or out of place in the upscale Hillsborough neighborhood.  In 2017, the property underwent some renovations and landscaping changes, including the addition of large dinosaur sculptures in the backyard, which further enhanced its Flintstones theme.

Ready to make Hillsborough your home?

The town of Hillsborough offers its residents quiet residential living within easy reach of downtown San Francisco. There are plenty of things to do around Hillsborough, whether you enjoy historic landmarks, family destinations, or a variety of outdoor pursuits. If you would like to learn more about Hillsborough or are interested in purchasing real estate here, reach out to the Sternsmith Group, a team of luxury marketing specialists and top Realtors® in the San Francisco Bay Area. Their attention to detail and commitment to customer satisfaction will make finding the perfect home in Hillsborough a breeze. Contact the team to begin your journey to homeownership today!
 

 

Casey Sternsmith

Casey Sternsmith

Founder

Get to Know Me

Meet Casey Sternsmith, founding partner of the Sternsmith Group. In business, exceptional service is what matters most to Casey Sternsmith.

With Casey at the helm of the Sternsmith Group, this level of commitment is shared by all members of the group who pride themselves on being excellent listeners with unwavering integrity, and for providing the best advocacy and negotiation skills for their buyers and sellers.

Casey’s philosophy of “love what you do, or do something else” is at the forefront of the entire team, which is evident by their true passion for helping clients achieve their real estate goals.
 
As a leader in real estate marketing, Casey employs tried and true traditional marketing as well as cutting-edge strategies such as social media marketing and professional videos for every home – from small condos to luxury estate properties. Casey’s clients also benefit from her vast personal network as a lifelong resident of the area.
 
As a result, she often achieves unprecedented outcomes for her sellers with quick sales and prices exceeding the list prices. To her buyers, Casey is known for excelling in competitive multiple-offer situations.
 
With more than 10 years of results that speak for themselves, Casey never looks at the process as a transaction, but rather as a personal decision and life choice that impact each and every day of their life. Because of this, a great deal of Casey’s personal business, and the Sternsmith Group’s as a whole, comes from repeat businesses and referrals.
 
Prior to her career in real estate, Casey owned and operated a personal training/Pilates studio in San Mateo where she honed her customer service, management, organization, and marketing skills. Combined with a bachelor’s degree from UC Santa Barbara, all of this proved to be the ideal foundation for her future success in real estate. Casey and her husband have two small children and reside in Hillsborough.
 
Tess Salter

Tess Salter

REALTOR®

Get to Know Me

Tess Salter is a top-ranked real estate agent in San Mateo County and a key leader of the Sternsmith Group, known for her exceptional negotiation skills, client-first approach, and record of delivering outstanding results. Tess has helped clients buy and sell homes across San Mateo, Burlingame, Hillsborough, Belmont, San Carlos, Redwood Shores, Redwood City, San Bruno, Millbrae, South San Francisco, Bay Meadows, Menlo Park, and Foster City. She specializes in single-family homes, condominiums, townhomes, luxury estates, and investment properties.

With over 10 years of experience, Tess has sold 71 homes in San Mateo County in 2025 and helped 61 buyers and sellers achieve over $125M in sales in 2024, according to RealTrends. Since 2015, Tess and her partner Casey Sternsmith have closed $1.3B+ in total sales, ranking them among the top 5 agents in San Mateo County and the #1 agents in San Mateo for seven consecutive years.

Tess was recognized by Gentry Magazine as one of the Top 10 Agents Under 40 in 2020, and the Sternsmith Group has been nationally recognized on The Leading 100 for the past seven years, celebrating the top-performing real estate teams in the San Francisco Peninsula.

Tess is known for her expertise in off-market listings, pre-market preparation, luxury marketing strategies, and customized property-specific marketing. She leverages Compass’ advanced technology, social media, and Facebook/Instagram Live tours to maximize exposure and deliver top results. With a strong foundation in finance, accounting, and economics, Tess provides data-driven insights that help clients make strategic real estate decisions.

Outside of real estate, Tess is deeply committed to her community. She served as PARCA Auxiliary President (2024–2025), continues on the PARCA Board (2019–2025), volunteers in Hillsborough schools, served on the West Elementary School Site Council, and chairs the Relay for Life for the American Cancer Society.

With 150+ five-star reviews and a reputation for integrity, responsiveness, and personalized service, Tess Salter and the Sternsmith Group provide exceptional guidance, strategic marketing, and unparalleled support for anyone buying or selling in San Mateo County, Burlingame, Hillsborough, and surrounding Peninsula neighborhoods.

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