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California Wine Country Road Trip

Northern California's Anderson Valley is what Napa used to be 30 years ago.
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Rating: 5 out of 5 by EveryTrail members
Difficulty: Easy
Duration: Multiple days

Overview:  The nearby town of Healdsburg acts as a sophisticated jumping-off point for this rural paradise, whose remote location and sleepy vibe... more »

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Points of Interest

1. 14feet

Vintage furnishings with an industrial-meets-schoolhouse bent (drafting tables, Thonet chairs) are arranged into photo-ready vignettes.

Address:
325 Center St.
Healdsburg, California
United States

Phone:
(707) 433-3391

2. Anderson Valley Brewing

Award-winning beers, plus seasonal releases (look for the Deep Enders Dark Porter).

Address:
17700 Hwy. 253, P.O. Box 505
Boonville, California
United States

Phone:
(800) 207-2337

The folks at the Philo Apple Farm once owned the French Laundry; now they grow 80 varieties of apples and rent out four charming cottages. Everything seems art-directed at the four-room property—from the honor-system harvest stand to the arbor-shaded table for alfresco dinners. A homey breakfast of toast and the farm’s own addictive jam awaits... More

4. Arboretum

The most fashion-forward boutique in town specializes in stylish, sustainable attire for men and women—from organic cotton T-shirts by Turk + Taylor to an Edun dress in sapphire silk.

Address:
332 Healdsburg Ave.
Healdsburg, California
United States

Phone:
(707) 433-7033

5. Bates & Mailliard Farmhouse Mercantile

This well-curated general store turns everyday items like Mason jars and balls of twine into exquisite collectibles.

Address:
14111 Hwy. 128
Boonville, California
United States

Phone:
(707) 895-3996

A modern roadhouse where each of the 10 colorful rooms features hillside views.

Address:
14050 Hwy. 128
Boonville, California
United States

Phone:
(707) 895-2210

Pig is something of an obsession at this petite café at the back of Copperfield’s Books. You can get the house-made bacon on a salad, in a sandwich, on pizza, or on pasta. Or throw dietary caution to the winds and dive into the pork-cheek sandwich.

Address:
106 Matheson St., Inside Copperfield’s
Healdsburg, California
United States

Phone:
... More

8. Breggo Cellars

The name means “sheep” in Boontling—a nod to the property’s former life as one of the oldest sheep ranches in the region.

Address:
11001 Hwy. 128
Boonville, California
United States

Phone:
(707) 895-9589

9. Cyrus

Sonoma Valley dining doesn’t get any finer than it does here, at this two-Michelin-starred restaurant set in Healdsburg’s Hotel Le Mars. The dining room—where the vaulted ceilings glow with golden light and where natty servers proffer selections from the caviar cart, cheese cart, and truffle humidor—encourages dressing up; and the sublime... More

Urbanites who prefer sleek, self-serve apartments to homey, antiques-filled B&Bs will appreciate the Duchamp, just two blocks off Healdsburg’s main plaza. The property’s six freestanding, metal-roofed bungalows are a study in clean-lined modernity, with poured concrete floors, flat-screen TVs, flokati rugs, and brushed-steel bathrooms. All... More

11. Esterlina Vineyards & Winery

Located in the hills, with panoramic views. Tastings are accompanied by bowls of Goldfish and Cheetos—a savory (if irreverent) touch. By appointment only.

Address:
1200 Holmes Ranch Rd.
Philo, California
United States

Phone:
(707) 895-2920

Known for iconic tableware that’s a favorite with modern-design fans and magazine prop stylists.

Address:
400 Gate Five Rd.
Sausalito, California
United States

Phone:
(415) 332-3732

Healdsburg’s historic downtown got a big dose of modern chic when this hotel opened in 2002, right on the main square. The property has a sophisticated, W-ish aesthetic, with common areas (a cavernous, firelit lobby lounge, a glassed-in breakfast atrium, a sleek outdoor pool) that feel luxe and decidedly angular. The 55 guest rooms are more... More

An Anderson Valley pioneer, housed in a charmingly rustic converted barn.

Address:
4400 Hwy. 128
Philo, California
United States

Phone:
(800) 554-8724

15. Lemons’ Market

Tom Lemons sells his own line-caught salmon.

Address:
8651 Hwy. 128
Philo, California
United States

Phone:
(707) 895-3552

16. Libby’s

Fresh ingredients and a surprisingly good wine list set Libby’s apart from your average Mexican restaurant. The carnitas are excellent, but so is the Caesar salad: lightly dressed and sprinkled with crunchy tortilla strips.

Address:
8651 Hwy. 128
Philo, California
United States

Phone:
(707) 895-2646

17. Mosswood Market & Café

As in a small-town version of Cheers, you’ll see the same faces reading the paper or tucking into a bowl of homemade granola.

Address:
1411 Hwy. 128
Boonville, California
United States

Phone:
(707) 895-3635

A popular draw for its affordable whites and outdoor picnic tables under trellised grapevines.

Address:
5601 Hwy. 128
Philo, California
United States

Phone:
(800) 537-9463

19. Other Place

With just four cottages on 550 acres, it’s easy to find solitude at the Other Place, hidden more than a mile down an unpaved road. The décor is deliberately simple, all the better to let the scenery be the star.

Address:
Boonville, California
United States

Phone:
(707) 895-3979

20. Phillips Hill Estates Winery

Remarkable Pinots made by artist Toby Hill (grab his ’07 Marguerite—if you can get it).

Address:
8627 Hwy. 128
Philo, California
United States

Phone:
(707) 895-2209

From the French makers of Cristal: sparkling wines at a much more budget-friendly price, in the valley’s poshest setting.

Address:
4501 Hwy. 128
Philo, California
United States

Phone:
(707) 895-2288

22. Standish Wine Company

The most photogenic tasting room in the valley, in a 19th-century wooden building once used for drying apples.

Address:
5101 Hwy. 128, PO Box 181
Philo, California
United States

Phone:
(707) 895-9213

Founded by retired fire captain Vern Boltz, this small, deceptively humble operation produces much-lauded wines and exceptional grapes.

Address:
8001 Hwy. 128
Philo, California
United States

Phone:
(707) 895-2828