Recently rated #2 on Smithsonian.com’s list of America’s best small towns, Healdsburg, California is a mecca for food, wine, and jazz lovers. Nestled between the rolling hills of Napa Valley and the cliffs of the Pacific Coast, Healdsburg embodies the laid back, grow-it-yourself mentality of Sonoma County. What was once a small agricultural outpost is now a bustling cultural hub featuring a central plaza lined with boutiques, bookstores, tasting rooms, and restaurants. But don’t let the au courant veneer fool you because the roots still run deep in Healdsburg, roots that are deeply entwined with the vineyards. Healdsburg is the convergence point of three of the country’s premier wine appellations: Dry Creek Valley, Russian River Valley, and Alexander Valley. Known for its Sauvignon Blanc, Chardonnay, and Cabernet Sauvignon,  the Alexander Valley’s Hanna Winery is a must see for wine enthusiasts. Perched on a hill overlooking the valley, Hanna Winery offers a Mediterranean tasting room and a variety of tours. Those who want to indulge in Healdsburg’s world-famous Pinot Noir should head to the Russian River Valley’s Arista Winery and enjoy tasting and a picnic in their scenic Japanese water garden. Rated as one of Bicycling Magazine’s 7 greatest rides on earth, cyclists must ride the winding Dry Creek Road through redwood forests, perhaps stopping at a winery at the end of a scenic day. The town’s central plaza (which is only minutes from any given winery) livens up in the evening. While Healdsburg offers a host of upscale restaurants, I would recommend the Barndiva. Located in a renovated barn at the heart of town, this indoor-outdoor restaurant champions all things local. The menu features exclusively local food and wine; and, your meal will come with musical accompaniment (most likely of the jazz variety). If you feel like getting out of town, take the Russian River Road to the Sonoma coast, or make the short trip East to Geyserville, home to the famous Coppola Winery!  Local food, local wine, and good people!