GETTING THERE Healdsburg is an hour's drive north from San Francisco or northwest from Napa WHEN TO VISIT High season runs from May through September; better deals are available midweek, or in October, when grape crushing is winding down RESOURCE For an introduction to the town, book a walking tour with expert Darla Meeker (www.healdsburgwalkingtours.com)
SLEEP Healdsburg's transformation began in 2001 with the opening of the Hotel Healdsburg (25 Matheson St.; 800/889-7188 or 707/431-2800; www.hotelhealdsburg.com; doubles from $325, including breakfast), co-owned by chef Charlie Palmer. The 55-room hotel is done up in an earthy palette inspired by its surrounding landscape: olive- and leaf-green walls, pecan-wood plank floors, and teak headboards that crown the downiest bed you'll ever sleep on. • The 16 over-the-top rooms at the new Les Mars Hôtel (27 North St.; 877/431-1700 or 707/433-4211; www.lesmarshotel.com; doubles from $525), which is modeled after a French château, are decked out with four-poster canopy beds and 17th- and 18th-century antiques. • Duchamp (421 Foss St.; 800/431-9341 or 707/431-1300; www.duchamphotel.com; doubles from $325, including breakfast) is a minimalist's dream come true: six bungalows with polished concrete floors warmed by sheepskin throws, cavernous white-and-black bathrooms, and clean-lined custom blond-wood furniture. Breakfast is served poolside, at café tables shaded by olive trees. • Healdsburg Inn on the Plaza (112 Matheson St.; 800/431-8663 or 707/433-6991; www.healdsburginn.com; doubles from $225, including breakfast) is the town's latest arrival. Rooms are sunny, with high ceilings, bay windows, fireplaces, and claw-foot bathtubs. For maximum privacy, we like the carriage house, which comes with a full kitchen and its own patio.
EAT "Eat local" is a rallying cry throughout northern California; in Healdsburg, many chefs are putting their menus where their mouths are. At Dry Creek Kitchen (317 Healdsburg Ave.; 707/431-0330; dinner for two $110), chef Palmer serves only Sonoma County wines—650 of them—and spotlights regional purveyors in dishes like chestnut-glazed squab. • Light-flooded and tranquil by day, Barndiva (231 Center St.; 707/431-0100; dinner for two $70) roars to life at night, when locals and in-the-know visitors descend on the big red barn for late-night meals, creative cocktails, and the hippest scene in town. • Newcomer Cyrus (29 North St.; 707/433-3311; dinner for two $116) amps up the glamour with dramatic vaulted ceilings and a theatrical reception: the maître d' phones the chef to announce your arrival, cueing the tableside champagne-and-caviar cart. Warm, intuitive service and exquisite dishes (truffled red-wine risotto, Thai marinated lobster) by rising chef Douglas Keane save the place from feeling pretentious. • The rustic Oakville Grocery (124 Matheson St.; 707/433-3200; www.oakvillegrocery.com) is a one-stop shop for discriminating picnickers. Call ahead for a gourmet packed lunch, or assemble your own from its selection of handmade cheeses, charcuterie, wine, and freshly baked bread.
SHOP The pea-sized 21 Arrondissement (309 Healdsburg Ave.; 707/433-2166) showcases interior designer Myra Hoefer's best French flea-market and estate-sale finds: a pair of gilt-and-velvet armchairs, a giant papier-mâché pinecone (formerly a Paris Opéra prop), and jewel-toned silk-screened pillows. • Scout (125 Matheson St.; 707/431-0903) is a mash-up of beach cottage and kaleidoscope, where gingerbread- trimmed shelves brim with kids' clothes in a riot of colors and patterns. • Baksheesh (106B Matheson St.; 707/473-0880) focuses on fair-trade, handcrafted gifts from the developing world, including carved beechwood bowls from Haiti and djembe drums from Burkina Faso. • Scoop up Sonoma County's best artisanal goodies at Plaza Farms (106 Matheson St.; www.plazafarms.com). Here's your cheat sheet: DaVero's Meyer-lemon olive oil, sheep's-milk cheese from Bellwether Artisan Creamery, and homemade salumi from Bovolo. • M Clothing (381 Healdsburg Ave.; 707/431-8738) is stocked with women's designs from both established and emerging labels. This season, look for eyelet tunic dresses by Burning Torch, straight-leg jeans by Notify, and sexy habotai (Chinese silk) shirts by Rozae Nichols. • Overseen by Lisa Palmer (Charlie's wife), Lime Stone (315 Healdsburg Ave.; 707/ 433-3080) sells restaurant-quality dining furniture and tabletop accessories (durable slipcovered chairs, affordable crystal stemware) alongside a global assortment of antiques.
DO There are more than 12 tasting rooms located within a square mile of the plaza; among our favorites are Thumbprint Cellars (36 North St.; 707/433-2393; www.thumbprintcellars.com), for its loungelike ambience and small-lot wines, and Toad Hollow (409A Healdsburg Ave.; 707/431-8667; www.toadhollow.com), for its unstuffy atmosphere and intriguing no-oak Chardonnay. • For a scenic drive through hillside vineyards and wineries, head west out of town on Dry Creek Road. Double back when you hit Lake Sonoma and return south on Yoakim Bridge Road, to link up with the winding West Dry Creek Road, peppered with a handful of small family-owned wineries.