California history melds with modern-day wine tasting rooms, art galleries and upscale shops in this picture-perfect country town in the northeast part of the valley (population 1,132). Centered by an iconic flagpole, Victorian homes and businesses cluster nearby around the community hub at the intersection of Grand Avenue and Alamo Pintado Avenue. Vineyards, lavender farms, orchards, ranches and horse trails surround Los Olivos. This is a charming place to visit for a one-stop wine country experience. It’s a laid-back place where locals sit on wooden porches and chat with friends and visitors; and most people wear jeans, cowboy boots and casual attire. The town dates back to the 1860s, when the stagecoach route began to pass through. County Historical Landmark Mattei’s Tavern was built to house and feed those passengers and now features a luxurious restaurant and bar. Many historic structures hold distinctly modern enterprises where you’ll discover retail treasures or can sip local vintages at a tasting room (choose among more than 30 within a 5-block area). The annual Jazz & Olive Festival every June attracts name performers and creative olive-centric cuisine from local chefs. Dine at a casual café or gourmet restaurant. Discover special annual events such as the Quick Draw Artists Festival (August), Day in the Country (October) and Olde Fashioned Christmas (December).