Ask a Healdsburg resident to describe this hamlet in northern Sonoma County and the reply will likely be couched in temporal terms: old Healdsburg or new? Before 2001, the town had family restaurants and local joints and just a sprinkling of visitors from far away. Then came the swanky Hotel Healdsburg and chef Charlie Palmer's acclaimed restaurant Dry Creek Kitchen—followed by boutiques, Michelin-starred eateries and, of course, tourists. Today Healdsburg is a remarkable synthesis of old and new—of small-town friendliness and big-city chic—of very good wine and equally good food. Here's what to do in Healdsburg and the surrounding valleys of northern Sonoma in just under three days.

Day One: Saturday

9 a.m. Land in San Francisco or Oakland, rent a car and start driving north via U.S. Highway 101.

11 a.m. First stop: Copain Wines, just off the highway in the Russian River Valley. Winemaker Wells Guthrie is acclaimed for his stylish Chardonnays and elegant Pinot Noirs and Syrahs. The winery is set on a high hill with dramatic views (sadly, only winery members may picnic on-site). My favorites tended to be the Pinots—most notably Kiser En Haut and Les Voisins. (Tastings by appointment only, at 11 a.m. and 2 p.m.; 7800 Eastside Rd., copainwines.com.)

1 p.m. Continue to the center of Healdsburg and have lunch at Bistro Ralph, a fixture on the town's plaza for more than 20 years (109 Plaza St., bistroralph.com). This casual Cal-French spot is a winemaker favorite, and its wine list reflects that. The daily fish special and the frisée salad are always good bets. Or head to the nearly year-old Campo Fina, where you can order a meatball sandwich on ciabatta bread and play a round of bocce (330 Healdsburg Ave., campo-fina.com).

Photos: Wine-Country Weekend Click to view slideshow Alanna Hale for The Wall Street Journal

2:30 p.m. The Hand Fan Museum is a two-block walk down Healdsburg Avenue. The tiny museum is stuffed with examples, some more than 100 years old. There are also a number for sale, priced from $20 to $150 (219 Healdsburg Ave., handfanmuseum.com).

3 p.m. Check into the Healdsburg Inn on the Plaza, built in 1901 and recently renovated. The rooms are bright and airy, with 12-foot ceilings. Breakfast is included and fresh-baked cookies are available almost all day (from $295 per night, 112 Matheson St., healdsburginn.com).

Oenofile: Northern Sonoma Take-Homes Click to view interactive F. Martin Ramin for The Wall Street Journal

3:30 p.m. Walk a couple of blocks to Flying Goat Coffee for a pick-me-up. My favorite was the Optimist's Blend, as much for its name as its mild, well-balanced flavor (324 Center St., flyinggoatcoffee.com).

4 p.m. There are several multi-dealer antiques markets within walking distance of the plaza. Healdsburg Vintage feels as if it's been around for decades but is less than a year old—and a tad swankier than the others (452 Healdsburg Ave., 707-433-5050). I found linens and kitchenware from the 1950s and '60s. Two other favorite markets require some patience and poking around: the disorderly but charming Antique Harvest (225 Healdsburg Ave.) and Mill Street Plaza (44 Mill St., 707-433-8409).

En route back to the hotel, stop by Healdsburg Shed, a new grocery-bar-cafe-home-and-garden store in a contemporary, glass-fronted space (25 North St., healdsburgshed.com). Plaza Gourmet (108 Matheson St., 707-433-7116) also stocks kitchen accessories, from the practical (measuring cups) to the decidedly quirky (a cow made from dried peppers).

7 p.m. Eat dinner at Scopa, next door to Bistro Ralph. It's a bit tucked away but the noise of the restaurant will guide you there. The crowd is lively, well-dressed and multigenerational, and the menu pays homage to traditional Italian fare (Nonna's tomato-braised chicken is a signature dish). The wine list is half Italian and half local (109A Plaza St., scopahealdsburg.com).

If the day has been long enough, grab a hotel cookie and head to bed; if not, swing by John and Zeke's Bar and Grill for a nightcap with the locals (111 Plaza St., 707-433-3735).

GRAPE ESCAPE | Vines at Duchamp Estate Winery Alanna Hale for The Wall Street Journal

Day Two: Sunday

9 a.m. Indulge in New Orleans-style beignets (five to a serving!) or shrimp-and-grits at Parish Café. Two blocks from the square, this newish spot uses local ingredients in traditional Crescent City fare (60A Mill St., theparishcafe.com).

11 a.m. Visit Skewis Wines' little metal-sided tasting room, situated in an enclave of wineries at the southern edge of town. The genial Hank Skewis has been making small-production Pinot Noirs since 1994 and knows a lot of great vineyards in Sonoma and the Anderson Valley of Mendocino. "I like a pretty vineyard," he confessed (57 Front St., skewis.com).

11:30 a.m. Head back downtown, stopping by the Oakville Grocery Co., a gourmet food shop on the square, for some picnic provisions (124 Matheson St., oakvillegrocery.com).

Noon Drive a couple of miles north on Healdsburg Avenue and turn onto Chiquita Road to Duchamp Estate Winery's SlaughterhouseSpace, an abbatoir that transplanted New York artist Pat Lenz turned into a gallery. Her fiberglass installations, by turns whimsical and thought-provoking, are scattered around the property; be sure to take a look inside Duchamp's head (by appointment; 280 Chiquita Rd., slaughterhousespace.com).

Illustration by John S. Dykes for The Wall Street Journal

12:30 p.m. Head north on West Dry Creek Road to the rolling hills of the Dry Creek Valley. Stop at Quivira Vineyards and Winery to visit the large organic garden, Ruby the pig and the beautiful chickens (yes, beautiful really is the word), and to taste the terrific Fig Tree Sauvignon Blanc, made in limited quantities. Ask for Ron Washam, a raconteur and local character who works the tasting room on Sundays (4900 West Dry Creek Rd., quivirawine.com).

Drive a few miles further north to Preston Vineyards, one of the most bucolic spots in the valley. Buy a bottle of the Preston Vineyards Sauvignon Blanc and a loaf of bread and eat lunch at one of the picnic tables scattered around the property (9282 West Dry Creek Rd., prestonvineyards.com).

3 p.m. Return to Healdsburg. Leave the car at the hotel and walk a couple of blocks to the Healdsburg Museum and Historical Society (221 Matheson St., healdsburgmuseum.org). Check out the current exhibit on actor and onetime Sonoma resident Fred MacMurray (through July 20) and pick up an $8 copy of "Historic Homes of Healdsburg" for a self-guided walking tour. The town has a mix of Victorian, Greek Revival and Italianate homes from the mid-1850s to the early 20th century.

Head back to the antiques markets if you like. Or stop by the new Sanglier Cellars tasting room (132 Plaza St., sangliercellars.com). They make a wide range of wines, including a rosé "inspired by Provence," according to owner/vineyard manager Glenn Alexander.

7 p.m. Dinner is at Mateo's Cocina Latina, around the corner and down the street. Chef Mateo Granados worked with Julian Serrano and Charlie Palmer at nearby Dry Creek Kitchen, then opened his own place, where he creates modern Yucatán cuisine from local ingredients. Ask bartender Sean Dal Coletto about the extensive mezcal and tequila selection (214 Healdsburg Ave., mateoscocinalatina.com).

9:30 p.m. Head a few blocks down Healdsburg Avenue to Bergamot Alley Bar & Wine Merchants for a nightcap. "All the industry people come here after work," said staffer Pedro Rusk (328A Healdsburg Ave., bergamotalley.com).

SIP AND DIP | Slip into the swimming pool at Francis Ford Coppola Winery. Alanna Hale for The Wall Street Journal

Day Three: Monday

8 a.m. Buy a flaky sticky bun across the plaza at Downtown Bakery & Creamery (308A Center St., downtownbakery.net). Locals show up early and tourists roll in a bit later.

10 a.m. While Ramey Wine Cellars' location may be less than beautiful ("across from a collision center and next to a vet clinic," said tasting host Tiffany True), the wines are first-rate. Winemaker David Ramey is one of the masters of Chardonnay and Cabernet. (Tastings available Monday through Saturday by appointment only, at 10 a.m. and 2 p.m., 25 Healdsburg Ave., rameywine.com.)

11:30 a.m. Check out of the hotel. Capture Wines' estate straddles Sonoma and Mendocino counties, but the proprietors hold private, by-appointment-only tastings of their superlative Sauvignon Blancs and Bordeaux-style reds in a Victorian house about a mile north of the inn (707-395-0457, capturewines.com).

Noon Drive about 10 minutes to the rather grand gates of Francis Ford Coppola Winery for a break from serious wine sampling (300 Via Archimedes, franciscoppolawinery.com). In addition to a tasting room, there's a swimming pool, cabanas, a bocce court, a teepee and two restaurants. Have lunch at the poolside cafe or on the terraces of Rustic, which features an Argentine grill. Check out the movie memorabilia. After a couple of hours, head back south on Highway 101. There's plenty more food and wine for another visit, another time.

Corrections & Amplifications

SlaughterhouseSpace is an art gallery at Duchamp Estate Winery in Healdsburg, Calif. The winery was incorrectly called Duchamp Winery in an earlier version of this article and an accompanying photo caption, and the gallery name was incorrectly styled as Slaughterhousespace in the article.