Healdsburg, California - Pictures of Healdsburg Wineries & Restaurants

Most of Sonoma County is like cotton: free-flowing yet down-to-earth. But then there’s Healdsburg. Healdsburg is linen: chic and sophisticated, yet always cool and comfortable. It's stylish without trying too hard.

Healdsburg is a pretty little town located in the perfect place. Three of the county’s most important wine-producing regions - the Russian River Valley, Dry Creek Valley, and the Alexander Valley - converge here. So, it wasn’t long before wine-lovers and other well-healed travelers started converging in Healdsburg as well. Soon enough, a supply of world-class restaurants, voguish boutiques, wine tasting rooms, and excellent hotels, spas and B&Bs, came to meet the demand.

Many of these shops and eateries surround the cute and bustling Town Square , which serves as the main social gathering spot. Go sit and relax at the old, iron bench across the street from the ever-popular Downtown Bakery & Creamery restaurant. This bench has been here since 1899 and has seen generations of daily life play out at this plaza. This is where the young people come to promenade and where the elderly couples come to watch them and reminisce. Moms bring their kids and teens bring their laptops. (It’s a WiFi hotspot.) And at the right time of year, when the oranges are ripe, everyone at the plaza tries to pluck a few of these juicy beauties off the tree. On Tuesday nights during the summer, some of the area’s best bands play at the Plaza for free. And a lively farmer’s market takes place during the same time.

And speaking of a great location…Healdsburg is also situated next to the Russian River , which winds its way languidly down to the ocean, offering swimming and kayaking opportunities.

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