Weekend Trips from Woodside, CA

Woodside, California, is a town renowned for its serene landscapes, equestrian estates, and proximity to Silicon Valley. Nestled among the redwoods and foothills of the Santa Cruz Mountains, Woodside offers a tranquil lifestyle that feels worlds away from the bustle of nearby tech hubs. But even with its natural beauty and luxurious living, the surrounding region offers an abundance of opportunities for weekend exploration. From coastal retreats and wine country escapes to cultural city breaks and nature adventures, weekend trips from Woodside, CA offer residents an exceptional variety of experiences—all within a few hours’ drive.

Just over two hours south of Woodside lies the iconic coastal village of Carmel-by-the-Sea. Known for its European flair, white-sand beaches, and artistic community, Carmel is the perfect destination for a romantic or rejuvenating weekend escape. Visitors can spend their days exploring boutique galleries, strolling through quaint courtyards, or enjoying wine tastings at downtown tasting rooms. For those craving outdoor adventure, the nearby Point Lobos State Natural Reserve offers scenic hiking trails, ocean vistas, and wildlife spotting opportunities. With its blend of elegance and natural beauty, Carmel-by-the-Sea remains one of the most popular weekend trips from Woodside, CA for residents seeking relaxation with a touch of culture.

For a luxurious weekend immersed in viticulture and gourmet experiences, few destinations rival Napa Valley. Located just under two hours from Woodside, Napa offers an indulgent escape with its acclaimed wineries, Michelin-starred restaurants, and spa resorts. Whether sipping Cabernet Sauvignon at a family-run vineyard or enjoying a mud bath in Calistoga, the valley provides both excitement and serenity. The scenic Silverado Trail and the iconic Napa Valley Wine Train offer unique ways to experience the region. For residents of Woodside, Napa is a favorite destination that delivers sophistication, romance, and world-class hospitality all in one.

A four-hour drive northeast of Woodside brings you to the alpine paradise of Lake Tahoe. Famous for its crystal-clear waters and majestic mountain backdrop, Lake Tahoe offers activities for every season. In the winter, ski resorts like Squaw Valley and Heavenly attract snow lovers, while the summer months are ideal for kayaking, hiking, and lakeside relaxation. Couples, families, and adventure-seekers alike find plenty to enjoy here. Whether it’s cozying up in a luxury cabin or exploring the area’s abundant trail systems, Lake Tahoe remains a premier destination for weekend trips from Woodside, CA that combine active recreation with breathtaking scenery.

Just a 45-minute drive from Woodside, Santa Cruz offers a laid-back coastal escape perfect for a spontaneous weekend getaway. Known for its surf culture, beach boardwalk, and eclectic arts scene, Santa Cruz caters to a diverse range of interests. Spend your days catching waves at Steamer Lane, enjoying retro amusement rides on the historic boardwalk, or exploring the redwood forests of nearby Henry Cowell Redwoods State Park. Santa Cruz’s unique charm makes it one of the best close-to-home weekend trips from Woodside, CA for families, couples, and solo travelers alike.

For those seeking a more remote and introspective escape, Mendocino is a hidden gem along Northern California’s coastline. Approximately four hours north of Woodside, this cliffside village is known for its dramatic coastal views, artsy community, and Victorian architecture. Activities include visiting the Mendocino Art Center, hiking in Mendocino Headlands State Park, and whale watching during migration season. The town’s slower pace and romantic ambiance make it a top choice for quiet weekend trips from Woodside, CA, especially for those looking to unplug and reconnect with nature and creativity.

Perhaps one of the most iconic drives in California is along Highway 1 to Big Sur. Just under three hours from Woodside, Big Sur offers towering cliffs, windswept beaches, and panoramic ocean views that are nothing short of awe-inspiring. Highlights include Bixby Bridge, McWay Falls in Julia Pfeiffer Burns State Park, and the cliffside restaurant Nepenthe. For those who enjoy hiking, the Ventana Wilderness provides access to rugged backcountry trails and redwood groves. Big Sur’s raw beauty and spiritual energy have inspired generations of writers and artists, making it one of the most enriching and scenic weekend trips from Woodside, CA.

For a convenient and serene retreat, Half Moon Bay is less than 30 minutes from Woodside but feels like a world away. With its coastal bluffs, tide pools, and charming downtown, it’s a great choice for a low-key weekend filled with fresh air and sea breezes. Enjoy a stay at the Ritz-Carlton overlooking the Pacific Ocean, take a walk along the Coastal Trail, or explore local farms and nurseries. Known for its pumpkin patches and annual Half Moon Bay Art & Pumpkin Festival, the town offers seasonal appeal throughout the year. It’s an easy and elegant weekend trip from Woodside, CA for those who want to escape without traveling far.

For dramatic natural beauty and outdoor adventure, Yosemite National Park is one of the most iconic destinations in the country. A four-hour drive from Woodside delivers towering granite cliffs, ancient sequoias, cascading waterfalls, and vast meadows. Whether you’re hiking the Mist Trail to Vernal Falls, taking in views from Glacier Point, or simply relaxing by the Merced River, Yosemite offers a majestic weekend retreat. Booking lodging in the park or nearby towns like Mariposa or Oakhurst can enhance the experience. For Woodside residents who crave connection with nature on a grand scale, Yosemite is a must-visit weekend trip that never fails to impress.

Just across the Golden Gate Bridge, Sausalito and the surrounding Marin County offer a mix of coastal charm, upscale boutiques, and outdoor adventures. Spend a weekend browsing local art galleries, dining at waterfront restaurants, or exploring the Marin Headlands for panoramic views of San Francisco Bay. Nearby Muir Woods National Monument is home to old-growth redwoods and serene walking paths. The blend of luxury and nature makes Marin a perfect balance of leisure and exploration. As one of the more accessible weekend trips from Woodside, CA, it’s ideal for a spontaneous getaway packed with charm and culture.

While Napa gets much of the attention, Sonoma County offers a more laid-back but equally delightful wine country experience. Located about two hours from Woodside, Sonoma boasts award-winning wineries, farm-to-table restaurants, and scenic drives through vineyard-covered hills. Enjoy a weekend filled with wine tastings in Healdsburg, exploring the Russian River, or taking a culinary class at a local cooking school. For a tranquil and less touristy wine country escape, Sonoma is one of the most rewarding weekend trips from Woodside, CA for food and wine lovers alike.

A little over an hour south of Woodside, Monterey offers a mix of marine life, historical significance, and coastal charm. Visit the world-famous Monterey Bay Aquarium, explore Cannery Row, or enjoy oceanfront cycling on the Monterey Bay Coastal Recreation Trail. Lovers Point Park in nearby Pacific Grove provides one of the best sunset views along the coast. With its combination of education, entertainment, and natural beauty, Monterey is a fantastic choice for family-friendly weekend trips from Woodside, CA or for couples looking to combine romance and exploration.

About three and a half hours from Woodside, Paso Robles has emerged as a premier destination for Central Coast wine tasting and wellness. The area features more than 200 wineries and is known for its bold reds and farm-driven cuisine. Spend a weekend touring vineyards, soaking in local hot springs, or enjoying live music at a countryside tasting room. The slower pace and open landscapes create a relaxing environment perfect for recharging. For Woodside residents interested in discovering a wine region with character and charm, Paso Robles is one of the more underrated yet rewarding weekend trips from Woodside, CA.

For a wellness-focused weekend, Calistoga in the upper Napa Valley offers mineral-rich hot springs, therapeutic mud baths, and vineyard views. Located two and a half hours from Woodside, Calistoga is ideal for a retreat centered around health, healing, and indulgence. Enjoy a massage at one of the town’s boutique spas, dine al fresco in a vineyard garden, and unwind with a glass of local wine at sunset. As a lesser-known but highly luxurious escape, Calistoga offers a unique alternative to mainstream destinations and makes for one of the most relaxing weekend trips from Woodside, CA.

Weekend trips from Woodside, CA offer more than just a quick escape—they’re a testament to the region’s unmatched access to natural beauty, culture, and luxury. Whether it’s a coastal drive to Big Sur, a wine-filled weekend in Napa, or a snowy getaway to Lake Tahoe, Woodside residents are never far from world-class destinations.

If you’re considering making Woodside your home—or if you're already a resident looking to make your lifestyle even more enriching—connect with Scott Dancer. As a seasoned real estate expert in Woodside, Scott offers insider knowledge, professional guidance, and a passion for helping clients discover not only the right home, but the right lifestyle.

Let Scott Dancer show you why Woodside living means having the best of California at your doorstep.