A Dreamy Drive Through California's Redwood Country

At almost the same time, my oldest and dearest friend, Megan, a book critic from back East, reached an inflection point of her own: her first pregnancy. We’re not “girlfriend getaway” types, which is why we thought it would be fun to have one—a last hurrah for her, a new beginning for me. Rather than follow the tourist-traced paths of Napa and Sonoma wine country, we’d seek out more off beat locales en route to and from Mendocino, a preserved-in-amber Victorian village about 150 miles north of San Francisco. Megan, five months along, would be eating for two—and I’d consume enough Pinot Noir for both of us.

We set off on Route 1, snaking along fog-enshrouded Mount Tamalpais, through fragrant eucalyptus groves and past the popular oyster shacks along Tomales Bay. The hills turned quickly from green to gold, and the rocky Pacific coast reemerged, each vista even more Instagrammable than the last. Playing the Thomas Haden Church character from Sideways to my Paul Giamatti, Megan teased me that I was going to meet a man on this trip.

When we reached Guerneville, a Twin Peaks-esque town 13 miles inland along the redwood-shaded Russian River, it was raining men—though not, it quickly became evident, the sort that might be interested in me. These were brawny, bearded guys in tank tops traveling in pairs and packs.

At Boon Hotel & Spa, a stylish inn just outside town, our post-drive nap was interrupted by a blast of “Blurred Lines.” A party had spontaneously erupted in the saltwater swimming pool. Two men in neon Speedos played chicken; one said of Megan, “Hey, it’s Nicole Kidman! And she’s knocked up!” I dipped a toe into the hot tub and realized I’d forgotten my swimsuit. “You can borrow one of mine,” offered a woman greased with glitter. “Or go without.”

Instead we rode into town on the hotel’s complimentary bright orange bikes. At the Sunday flea market, the sign on a crystal vendor’s dollar bin caught my eye: “Aids in finding, maintaining, or completing sexual relationships.” Sold.

After weaving through the throngs outside downtown’s handful of saloons—whose signs advertised beers for bears—we dug in to rock-cod tacos at the popular Seaside Metal Oyster Bar, opened last year by the owners of San Francisco’s Bar Crudo. Down the street, at the Guerneville Bank Club—a sort of artisanal mini-mall—we devoured coriander-raspberry ice cream from Nimble & Finn’s while perusing the indie travel magazine Cereal at Commerce Fine Goods, a lifestyle boutique that felt more Brooklyn than bear country.

We set off on another sublime cruise along the coast to the Sea Ranch, a spread-out community of timber-framed, shingled houses that almost disappear into the oceanfront meadows. The place is catnip for design lovers—I bought a mug with the ranch’s iconic ram-and-Helvetica logo at Sea Ranch Lodge’s gift shop. Just up the road, we found the Sea Ranch Chapel, a 1985 hippie masterpiece that resembles a wooden whirling dervish on the outside and a seashell on the inside. I suggested we meditate on the hand-hewn benches, but we couldn’t stop fidgeting.

We were eager to get to Mendocino and, especially, to our room at the John Dougherty House, with its sweeping ocean views and Brobdingnagian bathtub. “It’s like we’re on some sort of honeymoon,” Megan said. (The manager seemed to think so too, when we checked in.) But rather than spend all day in the room, we ventured out for dinner across the street at Trillium, an inn with a 20-table locavore café downstairs. We walked off the miso-ginger prawns and artisanal cheese platter along the bluffs of Mendocino Headlands State Park on the edge of town, taking in the sunset view of the Big River emptying into the sea.

We wandered Mendocino’s storybook blocks, passing an organic food co-op housed in a converted church and shops hawking souvenirs: T-shirts that read keep calm and get high, landscape paintings, folksy quilts. We found relief from the kitsch at Honey & Ro, a new boutique that stocks breezy blouses from cult Brooklyn brand Ace & Jig alongside Malian indigo throws and Turkish hand towels. The other retail standout is Old Gold, where I fancied a featherweight choker that spiraled around my neck like a Slinky, while Megan left with a pair of diamond studs that sat flat on her ears, a pre-motherhood gift to herself.

Our dinner destination, Wild Fish, neighbors a gas station and post office a few miles down Route 1 in Little River. The organic, ocean-centric menu—mostly sourced from local farmers and fishermen the same day it’s served—was as transcendent as the seaside setting. After polishing off an arugula-strawberry salad and the wild king salmon, Megan declared, “That’s the best meal this baby has ever eaten.”

After a stroll on the Big River’s broad, sandy banks, we whizzed through the redwood canopy south on Route 128. Was 11 a.m. too early to start wine tasting? Not at the Madrones, a Mediterranean compound in Philo that houses boutique hotel rooms, a serene rose garden, the Stone & Embers restaurant, and four tasting rooms. I fell in love with Bink Wines, mostly for its velvety Syrah.

We buzzed onward to Boonville, whose tiny downtown hosts quirky shops like Farmhouse Mercantile, a rustic-chic housewares haven. I pawed handloomed linen table runners and basketball-size Edison bulbs, imagining them inside the converted barn I might one day own nearby, while Megan stocked up on organic-cotton onesies.

The road grew windier, hairpinning past gnarled oaks and the odd lone horse. Megan was beginning to get carsick, so she was visibly relieved when we reached the comparatively tame Highway 101 an hour or so later. This led to Santa Rosa, which, as the largest city in Sonoma County, has a more low-key flavor than posh vacation spots like Healdsburg. Tipped off by a native, we hit Willi’s Wine Bar, a roadhouse-style institution, for tapas like Tunisian-style roasted carrots and heirloom tomatoes in kumquat oil.

Santa Rosa is also a booming brewery town, and in the spirit of journalistic due diligence I felt I had no choice but to sample the hoppy, heady IPA at the new, loftlike Cooperage Brewing Co. before continuing back to the city. As if starring in a buddy movie, we bopped along to Depeche Mode’s Violator as we crossed back over the Golden Gate. My heart may have been lonely, but I felt sated and elated. What are friends for?