In my seven years of living in Northern California, I had always thought of the Santa Cruz Mountains, which stretch along the peninsula just south of San Francisco, as a day-trip destination. Roughly an hour’s drive for most Bay Area residents, the region is filled with woodsy hiking trails and bikeable backroads dotted with farms, ranches, and vineyards. Close to home and full of activities, it’s no surprise so many people come here to spend the day outdoors.
However, those who choose to stay for longer will find no shortage of ways to turn a quick excursion into a full, nature- and food-filled weekend escape—something I’m sure we could all use right now. If you need a few days decompressing among the redwoods, glass of chardonnay in hand, use this guide to plan a weekend trip to the Santa Cruz Mountains.
Where to stay in the Santa Cruz Mountains
Although the Santa Cruz Mountains are close to several large and midsize cities, head into the forest if you want to make your getaway a real woodsy retreat. If you’re looking for a vacation rental, check around the towns of La Honda on the north end or Felton towards the south.
Canyon Ranch Woodside
Book Now: canyonranch.com
Nestled in a shady grove of redwoods and douglas firs on a newly rennovated property sits luxury wellness retreat Canyon Ranch Woodside. Smaller than its sister resorts in Tucson, Arizona, and Lenox, Massachusetts, the Woodside location—which first opened its doors in 2019—features a private hiking trail, garden, and spacious patios, all full of hidden spots to sit and relax outdoors. It also has 24 modern tree houses, which each have large, floor-to-ceiling windows and a small patio that will make you feel like you’re floating among the ancient trees.
Each stay includes a full program of activities ranging from hikes and workout sessions to yoga and meditation, as well as three delicious, healthy meals made by in-house chef Isabelle Jackson Nunes.
To comply with COVID regulations, Canyon Ranch Woodside is currently open to guests Thursday through Monday each week (private parties can book stays Monday through Thursday), and has restricted much of its programming to small groups outdoors.
Woodsy Silicon Valley Cottage
Book now: airbnb.com
If an Airbnb is more your style, look for a cozy place like this cottage in Portola Valley. Just a quick walk to several trailheads, and in between several of the area’s most popular wineries, this vacation rental makes for an easy jumping off point to explore the best of the Santa Cruz Mountains.
Things to do in the Santa Cruz Mountains
In the Santa Cruz Mountains, nature is at the forefront of everything. Day-trippers and weekenders alike come here to hike, bike, ride horses, and rock climb. Off-trail, the region is also home to a number of farms, ranches, and vineyards, some of which you can buy goods from and visit.
Spend the day mountain or road biking
Whether you prefer mountain or road biking, the Santa Cruz Mountains have seemingly endless opportunities for both. For a classic mountain bike trail, head to El Corte de Madera Creek Preserve where you can find a mix of trails, ranging from chill to technical. The rolling, 18-mile Skeggs-n-Eggs is a local favorite.
For road biking, plot your route along one of the less-crowded backroads that follow the mountain ridge for a mix of coastal and city views. You’ll find many cyclists on the classic Old La Honda–Tunitas Creek Loop, a mainstay in the region. If you venture towards the coast, be sure to pop by the famous Bike Hut on Tunitas Creek road to refill on food or bike supplies.
Tour art in the woods at Djerassi
There is no shortage of hiking trails in the Santa Cruz Mountains, but the Djerassi Artist Residency might just have the most distinctive one. Established by the Djerassi family in 1979, the nonprofit regularly hosts writers and artists to spend a month living and creating among the expansive, ridge-top ranch; many of them leave their art on the property to be discovered by curious visitors.
The result? Miles of trails dotted with hidden sculptures and nature-inspired art pieces that guests can explore on a guided, 3.5–4.5 hour-long sculpture hike. The hikes cost $50 per person and can be booked through Djerassi’s website.
Hike the redwoods or the coast
Although most visitors ordinarily head to the iconic Big and Little Basin State Parks to walk among the redwoods, the area was damaged badly in a recent fire and is closed until further notice. However, many nearby areas remain relatively undamaged and open to hikers, such as the Portola Redwoods State Park and Russian Ridge, which is popular for its coastal views.
Shop for local produce at a farm stand
Along the way to and from your excursions, keep an eye out for farm stands selling locally grown produce. If you’re lucky, you might just catch one with a freshly baked olallieberry pie, a regional speciality made from the small blackberry-like fruit that grows here.
Where to go winetasting in the Santa Cruz Mountains
Thanks to the mountainous terrain and narrow roads, visiting the often-hidden vineyards in the Santa Cruz Mountains is an adventurous experience. The rugged terrain and various microclimates also make this a good region for cool climate grapes, like Burgundy varieties of pinot noir and chardonnay.
Established in 2009 by a couple who left San Francisco to follow their dream of becoming winemakers, family-owned Mindego Ridge has since become an award-winning vineyard thanks to its high-quality chardonnays and pinots. Located in a wooded area a few minutes from La Honda, it currently offers small-group tastings by appointment on its breezy, open-air patio overlooking the grapevines.
Can’t make it there in person? You can also order its wines online.
Ridge Vineyards Monte Bello
In 1976, several California wineries shook up the wine world by beating out some of Europe’s best in a blind tasting—an event that would later become the basis for the 2008 film Bottleshock. One of those vineyards was Ridge Vineyards and its 1971 cabernet sauvignon, made from its original vineyard in Monte Bello.
To this day, it continues to make world-class wines that you can taste on a peaceful patio overlooking the mountains. To visit, book a tasting three or four days in advance on its website.
Just down the road from Canyon Ranch and several popular hiking and biking trails along Skyline Boulevard, Thomas Fogarty is a wonderful winery to visit and a great example of how the Santa Cruz region differs from its neighbors to the north. Make a reservation to sample a flight of Fogarty’s best wines on its vineyard-adjacent patio or, for an extra $10, pair your tasting with a tour of the property.
Where to eat and drink in the Santa Cruz Mountains
If you’re staying at Canyon Ranch, there’s no need to venture away from the property for good food. All three meals are included in guests’ stays, featuring fresh, healthy, and locally sourced creations by head chef Nunes. She channels her passion for local and high-quality ingredients to develop dishes for the daily menus, like chicken tortilla soup, breakfast crepes, or fresh little gem salads with homemade vinaigrette.
If you’re staying around Woodside or La Honda, the iconic Alice’s Restaurant isn’t just your best option—it’s pretty much your only one. Popular among the motorcyclists, hikers, equestrians, and outdoor adventurers who flock to the area, this 1900s-general-store-turned-restaurant serves up no-nonsense American fare made from sustainable and local ingredients. The menu focuses on classic breakfast and lunch fare: hearty omelettes, coffee cake, BLTs, and—of course—burgers. If you get the burger, go for the Farmer’s burger. “It’s worth the extra $4,” says Nunes.
Picnic at Harley Goat Farms
Moving away from the mountain range and towards the coast, you’ll find farms and ranches spread among the hills—some of which you can visit. We recommend a stop at Harley Goat Farms, which will take visitors on a tour to see how goat cheese is produced and say hello to the herd. (Want to see baby goats? Time your visit for the spring.) If you can, book a picnic for your visit and enjoy a farm-made lunch of soup, salad, and sandwiches that you can eat in a secluded garden.
Arcangeli Grocery Co.
Before you leave Pescadero, be sure to pop by Arcangeli Grocery Co. in the town center for a loaf of its famous garlic and artichoke bread. Made with locally grown artichokes, this bread is exactly the kind of savory, carb-filled treat you’ll want after an active day outside.
How to get to the Santa Cruz Mountains from San Francisco
From San Francisco, hop on the 280 south then exit to take CA-35, also known as Skyline Boulevard. From there, take a left on highway CA-84 to get to La Honda and Pescadero. A left on CA-9 will take you to Felton and, eventually, the city of Santa Cruz.
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