Hillsborough, California

Exploring the Hidden Gem of Hillsborough, California

Welcome to Hillsborough, California, a charming town nestled in the heart of San Mateo County. Located just minutes away from the bustling city of San Francisco, Hillsborough offers a peaceful retreat with picturesque landscapes, luxurious mansions, and a rich history. Whether you’re a nature enthusiast, history buff, or foodie, Hillsborough has something to offer for everyone. Join me as we embark on a memorable three-day weekend trip, filled with top-rated attractions, delectable dining experiences, and breathtaking sightseeing.

Day 1: Discovering Natural Beauty

Crystal Springs Reservoir

Start your day by diving into the natural beauty of Hillsborough at Crystal Springs Reservoir. This stunning man-made lake is surrounded by lush greenery and offers spectacular views of the San Francisco Peninsula. Take a leisurely stroll along the reservoir’s trails, breathe in the fresh air, and soak in the tranquility of the surroundings. Don’t forget your camera to capture the picturesque vistas.

Filoli Historic House and Garden

Next, immerse yourself in the grandeur of Filoli Historic House and Garden. This magnificent country estate, spread across 16 acres, boasts stunning gardens, a beautiful Georgian-style mansion, and a rich history dating back to the early 20th century. Explore the meticulously maintained gardens, filled with vibrant flowers, tranquil ponds, and elegant sculptures. Step inside the mansion to admire its timeless architecture and opulent interiors. Don’t miss the chance to indulge in a delightful afternoon tea at the charming Filoli Café.

Dinner at The Ritz-Carlton Half Moon Bay

As the day winds down, treat yourself to an unforgettable dining experience at The Ritz-Carlton Half Moon Bay. Located nearby in Half Moon Bay, this luxurious coastal resort offers a range of exquisite dining options. Whether you choose Navio, known for its delectable seafood dishes and breathtaking ocean views, or The Conservatory Lounge, perfect for enjoying handcrafted cocktails and small bites while gazing at the sunset, you’re in for a culinary treat. Sit back, relax, and savor the flavors while the sound of crashing waves serenades you.

Day 2: Historical Gems and Cultural Delights

Burlingame Museum of PEZ Memorabilia

Kickstart your day with a visit to the quirky yet fascinating Burlingame Museum of PEZ Memorabilia. This one-of-a-kind museum showcases an extensive collection of PEZ candy dispensers, dating back to the 1950s. Marvel at the colorful displays, learn about the history of these iconic collectibles, and perhaps even add a new dispenser to your own collection. It’s a nostalgic journey that will leave you with a smile.

Hillsborough Historic Society Museum

Continue your exploration of the town’s history at the Hillsborough Historic Society Museum. Housed in the historic Crocker Mansion, this museum offers a glimpse into the past of Hillsborough and its prominent residents. Admire the elegant architecture of the mansion and browse through the exhibits showcasing photographs, artifacts, and stories from different eras. The knowledgeable volunteers are always happy to share interesting anecdotes and answer any questions you may have.

Lunch at The Van’s Restaurant

Head to The Van’s Restaurant, a local favorite with a rich history and delicious cuisine. Located on the outskirts of Hillsborough, this restaurant offers stunning panoramic views of the San Francisco Bay while serving up mouthwatering American fare. Indulge in their signature prime rib or savor fresh seafood dishes, all while enjoying the warm and inviting ambiance. Don’t forget to save room for their famous homemade desserts.

The Peninsula Museum of Art

After lunch, make your way to The Peninsula Museum of Art, nestled in nearby Belmont. This contemporary art museum showcases a diverse range of local and regional artists, with exhibits that change regularly. Immerse yourself in the world of modern art, browse the thought-provoking installations, and appreciate the creativity on display. The museum’s serene atmosphere provides the perfect setting for reflection and inspiration.

Day 3: Outdoor Recreation and Culinary Delights

Sawyer Camp Trail

Start your day with an invigorating hike or bike ride along the scenic Sawyer Camp Trail. This 6.2-mile trail winds alongside the Crystal Springs Reservoir and offers awe-inspiring views of the water, surrounding hills, and abundant wildlife. Take your time to savor the natural beauty, listen to the sounds of nature, and relish in the peacefulness of the trail.

Lunch at The Waterfront Restaurant

After an active morning, treat yourself to a delicious waterfront lunch at The Waterfront Restaurant in nearby San Mateo. This local gem combines stunning views of the San Francisco Bay with an enticing menu featuring fresh seafood, juicy steaks, and flavorful vegetarian options. Indulge in their famous clam chowder or sample their sushi rolls, all while enjoying the relaxed and vibrant atmosphere.

Hillsborough Wine Company

No trip is complete without experiencing the local flavors, and Hillsborough Wine Company offers just that. Head to this boutique wine shop and tasting room to sample a variety of hand-selected wines from around the world. The knowledgeable staff will guide you through the tasting experience, sharing stories about each wine and helping you discover new favorites. Don’t forget to pick up a bottle or two to savor later as a memento of your trip.

Dinner at Pausa Bar & Cookery

For your final evening in Hillsborough, indulge in a culinary journey at Pausa Bar & Cookery. This Italian-inspired restaurant in San Mateo is known for its creative dishes crafted with locally sourced ingredients. From handmade pasta and wood-fired pizzas to flavorful appetizers and innovative cocktails, Pausa offers a delightful blend of tradition and innovation. Relax in the cozy ambiance, savor each bite, and toast to a wonderful weekend spent exploring Hillsborough.

As your three-day weekend trip in Hillsborough, California comes to an end, you’ll leave with memories of breathtaking natural landscapes, fascinating history, and unforgettable culinary experiences. Hillsborough may be a hidden gem, but it shines brightly with its unique charm and allure. Plan your visit, immerse yourself in the town’s wonders, and discover why Hillsborough is a destination worth exploring.

Please note that due to the ever-changing circumstances, it is essential to check the official websites of attractions, restaurants, and museums for updated opening hours and regulations before visiting.

Safe travels!

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