Road Trips

Fall Into Napa's Bucolic Small Towns and Iconic Wine Country

Words by Dylan RupertPhotography by Nicholas Albrecht

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Spottswoode Winery

Updated

11 Nov 2024

Reading Time

12 Minutes

Napa remains a classic world of small towns, roadside finds and wine.

It’s easy to think of the Napa Valley as inaccessible, cordoned off by big money and wine pretension. But the real Napa is an agricultural wonderland rich with history, with soil as fertile for grapes as for the California dream. You know that one: the vision of relaxed luxury in bucolic small towns, the one that draws romantics far and wide for magnificent wine, world-class food scene and unexpected cultural treasures.

Iconic stretches of Highway 29 and the parallel, two-lane Silverado Trail take you right into this daydream. This route from south to north also steers clear of some of the valley’s more hectic scenes in favor slow-paced charm. Salute!

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Goats at Spottswoode Winery.

Napa

Food Hall: Oxbow Public Market
Coffee: Naysayer
BBQ: Stateline Road
Wine Bar: Compline

Park it in Napa proper for a day exploring the small-town core of the Valley. More laid back than its touristy neighbors Yountville and St. Helena, Napa’s the cultural hub of the local scene—a small city with soul, industry and plenty of creativity in its nooks and crannies. Downtown, bisected by the Napa River, promises an easy, breezy day of strolling with coffee in hand, until it’s time to head to the viticultural edge of town and taste wine in its natural habitat.

Rancho Gordo Beans Headquarters

Heaven for bean freaks, the shop at culinary cult favorite Rancho Gordo HQ stocks a full portfolio of boggingly diverse heirloom bean varieties, cultivated in California or through partnerships with traditional growers in Mexico. The shop also sells niche Central American cooking ingredients, fan merch and cookbooks.

Folklore Records + Drinks + Food

Shop for vinyl and stay for a sip or a bite while community radio broadcasts out of the back at KCMU 103.3FM.

Ashes & Diamonds

Architectural chic reminiscent of Palm Springs frames vine-lined hills behind Highway 29, and the A & D winemaking team features a cast of heavyweights. The perfect way to experience their work is through the tasting menu experience, a showcase for the brand’s classic approach to California wine and the vibrant new energy it brings to the Napa scene. Reservations required.

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Napa & Sonoma

A landscape sublime. Wine country idyll. Valley vineyard upon valley vineyard. Beat poets. Back-to-the-landers. Moguls. Clink. Sip. Assess. Enjoy.

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Matthiasson Vineyards

Steve Matthiasson’s sought-after vintages reflect dedication to sustainable agriculture and an independence rare and admirable
in big-money Napa Valley. Reservations are required here, too.

Slanted Door

San Francisco’s iconic Vietnamese innovator settled in downtown Napa in a chic, airy space, where the refreshing cuisine is served in a beautiful courtyard.

Trancas Steakhouse

No, not for dinner. Come for this locally beloved spot’s main attraction: weekend karaoke in the bar. It’s a rare and special place where blue-collar locals, wine-stained retirees and festive daytrippers happily, sloshily coexist, if but for a moment, in (slightly out of tune) harmony.

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Ashes & Diamonds

Road Intel

CAMPGROUNDS
An intriguing RV option: Skyline Wilderness Park, just east of Napa (the town). Full and partial hook-ups are available, as well as dry camping. More than 20 miles of multi-use trail beckon hikers and mountain bikers. Napa Valley Expo RV Park is closer to the heart of town—walking distance, in fact.

NAPA → ST. HELENA

MILES: 19
PASTRIES: BOUCHON BAKERY
CHANDELIERS: RH YOUNTVILLE
GOURMET GROCERY: OAKVILLE GROCERY
BURGERS: GOTT'S ROADSIDE

This ramble is what people think of when they think Napa Valley: fine wine, farm-to-table cuisine and Silverado Trail lanes leading to vine-laced views and epic estates. Can most of us afford five-star hotels, multi-Michelin-star restaurants and top-drawer tastings every day? Maybe, maybe not. But with a little strategy, you can easily get a sample of all the above.

Stop in Yountville, sometimes lovingly referred to as an adult Disneyland, to stroll up and down its chic one-mile downtown artery, Washington Street. It’s dotted with tasting rooms, art galleries, restaurants and the perfectly manicured culinary gardens at the French Laundry, chef Thomas Keller’s all-timer prix fixe restaurant. Between Yountville and St. Helena, you’re in the thick of the old-school Napa wine world, with blockbuster names like Beaulieu, Mondavi, and V. Sattui. Once in St. Helena, a historic main street awaits exploration.

Bonus Trip

Sonoma from Calistoga, a 30-mile swing over the Mayacamas Mountains takes you to the town of Sonoma, epicenter of a very different Cali wine vibe.

Valley Bar + Bottle Shop, right on the historic plaza, gives a quick immersion into Sonoma’s crafty, low-key vibe. A four-minute walk away, Readers’ Books provides the long-running backbeat to the town’s cultural life. Locals who know, know that El Molino Central is the hangout for birria tacos and enchiladas. About five miles out of town, Scribe Winery is housed in an atmospheric hacienda and known for forward-looking winemaking. Visits are open to members of Scribe’s wine club, which is well worth it.

Sip: Lush and leafy Spottswoode Winery pioneered organic wine-making in Napa. The winery offers tours of their vineyards and gardens, and the most storied of Napa varietals, Cabernet.

Dine: When you want original, classic wine country chic with a minimum of pretension, head to Mustard’s Grill, a time-honored meet-and-greet spot. Dine among their gardens. Likewise, Elliot Bell, a veteran of French Laundry, offers a cheerful spot at Charlie’s. He showcases local purveyors via loosened-up California comfort cuisine. Think beer can chicken, oysters from Tomales Bay, abalone served Rockefeller-style and house-made Hawaiian rolls.

Screen: Built in 1913, St. Helena’s Cameo Cinema is California’s oldest continuously operated single-screen movie theater. It serves as an anchor for the region’s independent film scene, showing both box office hits and indie favorites alike.

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Exterior at Charlie's
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Wine offerings at Charlie's
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Lunch service at Charlie's
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Calistoga Farmers Market

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