Healdsburg Is Wine Country In Miniature

It's a walkable, well-heeled hub full of Sonoma County flavors.


Contemporary-but-casual Chalkboard finds inspiration in the region's produce.

Kristan Lawson



The Wine Country’s dirty little secret is that it revolves around two incompatible activities: drinking and driving.

In Sonoma County’s rural tasting rooms, the vino flows freely, and the collective blood-alcohol level soars, yet to travel between vineyards necessarily means automobile + inebriation = uh oh.

If only there were some centrally located, walkable wine hub.

Welcome to Healdsburg. Strategically positioned two hours from Oakland off Highway 101 at the intersection of Sonoma’s three main wine-growing appellations-Russian River, Dry Creek, and Alexander Valley-it’s recently blossomed from a dusty Victorian country town into a chic resort village.

Healdsburg’s bucolic slumber broke in 2001 with the opening of celebrity chef Charlie Palmer’s Dry Creek Kitchen restaurant. Upscale tourism had arrived, and now cafés, boutiques, and hotels flank a sylvan central square sporting an authentic vintage bandshell.

But you came for the wine. Two-dozen tasting rooms dot this peak-quaint downtown, which basks in a deep, grape-ripening countryside glow.

For a guilt-free non-driving wine tour, all you need to do is find a parking spot somewhere near Healdsburg Plaza and walk your way through Sonoma County in miniature.

Williamson Wines (www.WilliamsonWines.com) serves precise pairings of umami-rich appetizers with its own small-batch Cabernets. Nearby Thumbprint Cellars (www.ThumbprintCellars.com) blends grapes bought from the region’s best vineyards. And Cartograph Wines (www.CartographWines.com) offers a minimalist-moderne space favored by grape geeks.

Healdsburg caters to the well-heeled, unapologetically. Oakland’s similarly priced eateries serve up snark and irony with your farm-to-table meal; in Healdsburg, the same dining dollar buys elegance and unselfconscious indulgence. Search in vain here for graffiti, litter, postmodernism; you’ll find instead ivy-covered cottages, floppy sun hats, sincerity.

Snag local specialties at rustic Oakville Grocery (www.OakvilleGrocery.com/home/stores) and farm-chic SHED (www.HealdsburgShed.com). Dine away your blood-alcohol at trendy Chalkboard (www.ChalkboardHealdsburg.com), whose small-plate experiments utilize produce from its own garden.
At the north end of town, Simi Winery (16275 Healdsburg Ave., www.SimiWinery.com) is among the state’s oldest, once so important that it boasted its own train station.

In Healdsburg, authenticity isn’t an affectation.

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