Old West facades and horseshoe-embedded crosswalks hint at the cowboy charm of the Valley’s namesake. Mosey into town early for baked treats and coffee at The Baker’s Table. Then head to the Santa Ynez Valley Historical Museum to learn about the region’s history, including the Chumash Indians, ranchers, and see carriages on display from the old stagecoach route. Venture to nearby Sunstone Vineyards and Winery or Bridlewood Estate Winery for tastings, and take along a focaccia sandwich and provisions from Lucky Hen Larder. Side trips might include Summerset Farm for berries and jams, Rancho Olivos for local olive oil, and Quicksilver Ranch—recently up for sale—to meet the mini horses. No visit would be complete without a meal at S.Y. Kitchen, where you’ll find meticulously crafted cocktails and local wines to pair with excellent, modern spins on Italian fare showcasing local produce. Afterward, wet your whistle at the Maverick Saloon, a well-weathered country bar where you can see cows from the porch. Catch live country acts, pin dollars to the ceiling for luck and witness multiple wedding after-parties (there’s even a “Walk of Shame” drink special on Sundays).