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Say Hello to Healdsburg

In a galaxy where the stars of Napa and Sonoma shine like supernovas, there are a few glimmers in the sky that also command the attention of wine country stargazers. Take for instance the town of Healdsburg, for years content to exist in the outer reaches of what most people thought of as Wine Country. But these days, the gravitational pull is proving too great to resist.

Healdsburg is stepping out of its comfortable spot as supporting actor and into a leading role. The secret is out that the once sleepy town is a destination in its own right. And it doesn’t hurt that it’s just a short drive from San Francisco. Indeed during a recent weekend visit, it seemed as if half my San Francisco neighborhood was congregating in the bar at the Hotel Healdsburg.

What locals have known for decades, the rest of the world is finding out. Healdsburg offers the amenities and attractions of the bigger, better-known Wine Country towns while managing to retain a down-home charm and easy-paced lifestyle. Though it’s known as a great place for bicycle tours, much of Healdsburg’s charm is rooted in its walkability. The downtown core, anchored by a park-like plaza, is rife with shops, galleries, cafes, and restaurants. And in perhaps in no other part of Wine Country can you find so many tasting rooms accessible without having to drive. There are some 15 tasting rooms within a short walk of the town plaza.

Among them is Kendall-Jackson Healdsburg (337 Healdsburg Ave; 707-433-7102), near the northwest corner of the plaza. It’s the winery’s ancillary—and much smaller—tasting room, but it offers the full range of KJ wines. Also located on the square is an offshoot tasting room for giant Gallo of Sonoma (320 Center Street; 707-433-2458), which offers the well-known producer’s varietals for tasting by flight in a sit-down situation.

Lake Sonoma Winery (340 Healdsburg Ave; 707-473-2999) is also represented on the plaza. The tasting room is often packed with enthusiasts of the popular regional winery. Nearby is the stylish Mayo Family Winery’s Reserve Room (340 Center Street; 707-433-9400), which presents a refined, relaxed atmosphere in which to enjoy their small-lot wines. Taking the tasting concept up a notch, they also offer pairings with each tasting of small dishes prepared by the chef from the excellent next-door restaurant, Zin (344 Center Street, 707-473-0946).

Other tasting rooms in the downtown area include the friendly Toad Hollow (409A Healdsburg Ave; 707-431-8667), and Rosenblum Cellars (250 Center Street; 707-431-1169) an East Bay transplant that put down stakes just around the corner from the wildly popular Oakville Grocery.

Speaking of Oakville Grocery (124 Matheson St.; 707-433-3200), the third incarnation of the gourmet grocery store founded in Napa Valley is one of the best placed in Healdsburg to stop for an afternoon respite. The grocery has a retail component stocked with regionally produced gourmet products, as well as an alfresco café-style patio upon which to enjoy fresh-prepared treats from the kitchen. Not to be outdone by its neighbors, the grocery has a wine tasting bar, too.

Of course, for appetites beyond the gourmet grocery, Healdsburg seems to get better all the time. There are numerous excellent spots in the immediate vicinity of the plaza, but a few have lately been hogging the spotlight (deservedly so). At Dry Creek Kitchen (317 Healdsburg Ave., 707-431-0330;, big-name chef Charlie Palmer oversees an ever-changing array of seasonal Wine Country fare that has amassed a huge and slavish following (yours truly included). The place screams contemporary wine country chic, and the atmosphere imparts a feeling that you are connected to the immediate moment. 

For something a bit more refined but certainly not stuffy, there’s Cyrus (29 North Street, 707-433-3311;, whose intimate atmosphere has a European allure that is buttressed by a prix fixe menu offered in three or five courses. It’s all very civilized. Both of the aforementioned are associated with excellent hotels (Hotel Healdsburg and Le Mars Hotel, respectively), each providing a convenient waddle “home” when the day of wine tasting and eating in Wine Country’s newest “It” town is done.