Upscale accommodations and restaurants mingle with a folksy Main Street.
Cute-as-a-gilded-button St. Helena is anchored by an old-fashioned main street straight out of a Small Town, USA, postcard. Its bragging rights as the birthplace of Napa’s wine industry date back to 1861, when Prussian immigrant Charles Krug established the valley’s first winery here. Today, the town’s exclusive Meadowood Napa Valley resort, set at the foot of Mount St. Helena (and home to the prestigious three-Michelin-star Restaurant at Meadowood), is the site of the annual Auction Napa Valley. The vibe is more folksy along Main Street, where posh wine bars sit next to home-decor shops, clothing boutiques, and cozy restaurants. (707) 963-4456, sthelena.com . Area code is 707 except as noted.
Sample St. Helena’s agricultural bounty at Long Meadow Ranch, with estate-grown wine and olive oil and organic produce from the Hall family gardens and ranch (longtime fixtures at the local farmers’ market), and at the aptly named Farmstead restaurant, where nearly everything on the menu is grown on the ranch—including beef from their own grass-fed Scottish Highland herd. 738 Main St., 963-4555, longmeadowranch.com . At Bale Grist Mill State Historic Park, weekend visitors can watch demonstrations of the 36-foot waterwheel that powers an 1846 mill, a short hike from Bothe-Napa Valley State Park with its lovely picnic area and swimming pool popular with families in summer. On Highway 29, 3369 North St., 942-4575. Of the dozen shops along Main Street, Napa Valley Vintage Home stands out for its stylish and eclectic mix—decoupage plates to French milled soaps to Zutano baby clothes. 1201 Main St., 963-7423, napavalleyvintagehome.com . At Findings you can pick up wine-country home furnishings such as Adirondack chairs made from scorched wine barrels. 1269 Main St., 963-6000, findingsnapavalley.com .
Heavenly morning buns and pain au levain made from sourdough wine-grape starter are big draws at the Model Bakery, a downtown fixture since the 1920s. Fill your picnic basket with one of a dozen varieties of house-made breads—still baked in brick ovens built by Italian masons nearly a century ago. 1357 Main St., 963-8192, themodelbakery.com . Iconic St. Helena drive-in restaurant Gott’s Roadside (née Taylor’s Automatic Refresher) may have a new name, but it still dishes up a tasty burger, along with shakes, sweet-potato fries, spicy fish tacos, and a surprisingly good selection of wines served at what may be the state’s only drive-in roadside bar. Owners Joel and Duncan Gott have beefed up the seasonal menu specials with upscale items such as Korean-style pulled pork sandwiches and potato-leek soup; on warm nights, a picnic table on the lawn is “tray gourmet.” 933 Main St., 963-3486, gottsroadside.com . Wine country chef extraordinaire Cindy Pawlcyn brings a casual supper-club atmosphere and a full spectrum of festive cocktails to Cindy’s Backstreet Kitchen, where favorites include Chinatown duck burger and warm pineapple upside-down cake. 1327 Railroad Ave., 963-1200, cindysbackstreetkitchen.com .
The ambience of a country manor house with eight acres of landscaped gardens—not to mention two swimming pools, on-site winetastings, and rooms with fireplaces—make the Harvest Inn a magnet for weekend escapes. For AAA packages in St. Helena, including at the Harvest Inn, visit AAA.com . 1 Main St., 963-9463, harvestinn.com . Perched on the upper floors of a historic 1886 building overlooking downtown St. Helena, Hotel 1424 offers large rooms with granite kitchens, complimentary loans of Trek touring bikes, and free use of the pool and gym at the Napa Valley Spa down the street. From $119. 1424 Main St., 963-5100, hotel1424.com .
Photography courtesy St. Helena Chamber of Commerce
This article was first published in April 2011. Some facts may have aged gracelessly. Please call ahead to verify information.
Check out the rest of our Napa Valley  package:
Calistoga : Old West meets Old Faithful
Napa : budget restaurants and a bustling new riverside
Oakville : take a deep dive into wine culture
Rutherford : acclaimed wineries and exceptional natural attractions
Yountville : the Valley's fine-dining capital