Much as we all love it, a trip through the wine country can be a dubious undertaking—drinking wine (often in the sun) and then hopping in a car to head to the next place to drink more wine. That’s one reason why smart travelers are making their way to Healdsburg. In the past five years, scores of tasting rooms have sprung up around the main square of this lovely 19th-century town, which is right at the heart of three key wine-producing valleys. The other reason is apparent in the explosion of upscale shops, restaurants, and galleries that has utterly remade the community: no other former cow town on earth is more happening than Healdsburg. It’s also near some of the most picture-perfect countryside California has to offer. Rev up the motor if you feel so inclined, but a bike ride will get you as far as you need to go.

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Lake Sonoma Winery’s sophisticated tasting room, with its painted concrete floor and leather-paneled walls, is a crisp environment—perfect for sampling the winery’s chardonnays and sauvignon blancs. Nearby Toad Hollow, owned by Todd Williams (actor Robin’s brother), is friendly and unpretentious and offers lovely sparkling wines packaged with whimsical labels. The robust zins and knowledgeable staff at Rosenblum Cellars make it a top-tier destination for wine aficionados—we dare you not to walk out with several bottles. Lake Sonoma Winery, 340 Healdsburg Ave., 707-473-2999, www.lakesonomawinery.com; Toad Hollow Vineyards, 409 A Healdsburg Ave., 707-431-8667, www.toadhollow.com; Rosenblum Cellars, 250 Center St., 707-431-1169, www.rosenblumcellars.com.

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Hotel Healdsburg has long had its own in-house spa, but the new Koi Day Spa, opened in March, is a great independent place to get rubbed, waxed, or exfoliated into oblivion. Co-owner Tobi McCluskey’s specialties are three global-fusion body treatments: a Thai herbal poultice massage, a Javanese body scrub, and a Himalayan salt scrub. The hitch is that due to a problem with the building’s plumbing license, the spa doesn’t have showers, so don’t check out of your hotel before your treatment, or stick with one of the relaxing, customized facials with ingredients like pineapple, papaya, and pumpkin. 452 B Healdsburg Ave., 707-433-1270, www.koidayspa.com.

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You wouldn’t think a small town could outdo the big city, but Healdsburg has several shops that carry lines you won’t find in San Francisco. Out of Hand offers a variety of fun, contemporary clothing that urban fashionistas would easily drive 70 miles for. At Rainsong, the comfort shoes are shockingly stylish. The Healdsburg outpost of the Spirits in Stone gallery, which specializes in sculpture from Zimbabwe, carries a wonderful selection of the jewelry of San Francisco artist Sarah Graham. Her signature work incorporates blackened steel and white, black, and cognac diamonds, modeled after shapes found in nature. Out of Hand, 333 Healdsburg Ave., 707-431-8178, www.outof hand.com; Rainsong Shoes, 117 Plaza St., 707-433-8058, www.rainsongshoes.com; Spirits in Stone, 401 Healdsburg Ave., 707-723-7123, www.spiritsinstone.com.

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If money is no object, consider staying at Les Mars, the idea behind which was to marry modern-day comfort with old European style. Each of the 16 rooms has its own 17th- and 18th-century antiques, reproduction four-poster beds with lush Italian linens, and enormous Jacuzzi bathtubs. The hotel also offers activities like wine country mushroom foraging. For contemporary charm, Hotel Healdsburg is a good bet, with its welcoming lobby, spa, and pool. If Victoriana is your thing, try Calderwood Inn, a B&B just three blocks off the square that makes you feel like you’re off in the country. It offers a wonderful home-cooked breakfast at 9 a.m. and concierge services to help you plan area excursions. Les Mars, 27 North St., 877-431-1700, www.lesmarshotel.com, rates $475–$1,025; Hotel Healdsburg, 25 Matheson St., 800-889-7188, www.hotelhealdsburg.com, rates $260–$790; Calderwood Inn, 25 W. Grant St., 800-600-5444, www.calderwoodinn.com, rates $200–$270.