Daytrip: Healdsburg

Once upon a time, posh Healdsburg was a scrappy wine industry town that had little to appeal to daytrippers and tourists. But blessed with a Rockwellian town square, great weather and proximity to scores of world class wineries, the city reinvented itself into a wine country Aspen with outstanding hotels, restaurants and boutiques that attract visitors looking for something a shade more rootsy and rustic than the Napa Valley to the east. Chef Charlie Palmer’s Dry Creek Kitchen was one of the first restaurants to put the city on the map. Scores followed, including the Michelin three-starred Single Thread restaurant and recently opened Matheson restaurant and bar. Barn Diva, and newcomer Little Saint are other standouts. Other not-to-be-missed spots are Single Thread alums Melissa and Sean McGaughey’s excellent bakery Quail & Condor and Troubadour–a bakery and outstanding sandwich shop by day and bistro by night.

On the lodging front, Hotel Healdsburg helped establish the city’s reputation as a luxe getaway. The modern, 55-room hotel brings a little Manhattan glamor to Healdsburg. The eco-chic H2hotel down the street adds to the city’s portfolio with its LEED gold certified design and the outstanding Spoonbar, a restaurant and bar that pioneered the craft cocktail movement with ingredients straight from nearby gardens.

Healdsburg’s attractions aren’t all high-end. The heart of Healdsburg is its picturesque, 1850s-era town square complete with live music in the band shell and towering trees, including a rare Dawn redwood, the only deciduous conifer in the world that loses its needles every winter. Around the square, look for Copperfield’s bookstore, Noble Folk Ice Cream & Pie Bar and the excellent Duke’s Spirited Cocktails.

The nearby Russian River offers great paddling and swimming and Fitch Mountain, which rises like a knob above the city, offers challenging hikes with great views to match. Check out Badger Park, an 11-acre stretch of meadow with a meandering riverfront walk.

Healdsburg is of course a gateway to dozens of world-class wineries in the nearby Dry Creek Valley west of town and beyond. The way to see it all is via two wheels. With miles of sinewy roads that roll through vineyards, over bridges and up hillsides, Healdsburg is a cyclist's dream, especially with the great food and drink that awaits you after a long, hard ride.