This story is part of our September 2025 issue. To subscribe, click here.

Two hours from Sacramento, Woodside is where summer heat melts into the cool shade of redwoods and rolling coastal foothills. It’s a weekend swap of freeway hum for winding country roads, golden hills for lush green trails and everyday routines for horseback rides, hidden wineries and meals worth the drive. Tucked just inland from the San Francisco Peninsula in San Mateo County, this small town offers the kind of refresh that feels like a distant getaway — without the hassle of a flight or the crowds of the coast.

I planned my first stop at Filoli, an historic estate just outside of town. Although the main house is grand, the real draw is what surrounds it: acres of meticulously designed gardens. I wandered into the Walled Garden, a nearly one-acre enclosure bordered by high brick walls, where low hedges carve the space into a series of smaller garden “rooms.” Each one feels like its own restful and verdant little world.

Later I stumbled upon a kitchen garden where rows of vegetables, fragrant herbs and flowers grow in tidy, purposeful formation. Further on, winding paths meander through orchards and a meadow known for its spring daffodils.

From Filoli, I drove into Woodside’s small town center and stopped at Roberts Market, the local go-to for sandwiches, snacks and specialty everything. The deli line moved slowly, but no one seemed in a rush. A man in dusty boots ordered a BLT behind someone in full cycling gear. I grabbed a turkey sandwich and sat outside under a redwood, eavesdropping on a couple of retirees enjoying a slow travel excursion.

Then it was time to start my journey to my retreat. I drove up the mountain roads through switchbacks flanked with towering redwoods that provide a canopy of shade and stillness, a metaphor for what I was about to enter.

I discovered Canyon Ranch Woodside through a PR stint but have returned again and again when I need a reset from my busy life. I entered through automatic gray gates, eager for renewal, wellness and calm. The boutique resort boasts 38 rooms — 24 of them treehouses.

These elevated upscale suites, high in the forest, have floor-to-ceiling windows and are quiet sanctuaries built for grown-ups who need to rest and recharge. I felt more relaxed, refreshed and alive with each breath as I entered my treehouse suite, mesmerized by the height, strength and beauty of the coastal forest that surrounded me.

It is purposefully quiet here. Unlike other places I’ve visited in the past, where bright lights and music surround you, this retreat offers pure silence and stillness. I sat on my private patio in a long, wooden Adirondack chair, just staring at the trees and listening to the quiet that was only interrupted with the occasional owl hooting, birds chirping or a woodpecker hard at work. The gentle cascade of notes from wind chimes and soft trickling water from the fountains beckon me to enjoy the calmness.

During my stay, I walked the trails on the property. The Wander Trail and the Journey Trail are each less than a mile and provide more of a respite than a workout. I enjoyed walking alone, but you can participate in a group, such as Yoga on the Trail, to bring fresh air and open thoughts into your practice.

Along the trails I saw a Buddha statue where a meditation experience is held. I spent some solemn time in the forgiveness sanctuary, designed for reflection, emotional release and the kind of inner work most of us avoid until occasions like this summon us to embrace the opportunity to release. On my way back up the trail, I spotted a doe with her two fawns. She stared right at me, as if saying, “I understand.”

After my weekend stay, I was still eager to explore more of what Woodside had to offer. I made a stop for lunch at Buck’s, the town’s most famous restaurant, which earned its reputation in the ‘90s as a sort of de facto clubhouse for venture capital deals. The place is still covered wall-to-wall in weird memorabilia like giant cowboy boots hanging from the ceiling, a model of the space shuttle, old toys and even the world’s largest dog chew toy.

I had to be sure to check out the Woodside Store. It was built in 1854 and is now a museum that displays artifacts from the town’s logging history. The building has been on the National Register of Historic Places since 1985 and is listed as a California Historical Landmark in San Mateo County.

Woodside isn’t designed as a tourist destination — it’s a place made for those who call it home. But if you find yourself here, seeking calm, fresh air or a quiet escape among the trees, you’ll discover it welcomes you quietly, without fanfare or explanation. And somehow, that’s exactly what you need.

–

Stay up to date on business in the Capital Region: Subscribe to the Comstock’s newsletter today.