By Rachel Ing
In the 1880s, rumors that the Pacific Coast Railway planned to build a station in Los Olivos drew businesses, including a hotel, saloons, restaurants, and a theater, to this humble stagecoach stop in the verdant Santa Ynez Valley. The station was never built, and this town of 1,000 remained under the radar until indie favorite Sideways put Los Olivos on the map. Today, day-trippers visit the tranquil, walkable, five-block downtown for its wine-tasting rooms, art galleries, and restaurants, many of which are housed in historic 100-year-old buildings.
Found Around Town
Six-foot-tall wind chimes and a comically large red Adirondack chair beckon visitors to explore J. Woeste Home and Garden Treasures. Beautify your yard with succulents, sculptures, birdbaths, and garden gnomes. 2356 Alamo Pintado Avenue. (805) 693-1951; jwoeste.com.
At Barbieri Wine Company, Master Sommelier Paolo Barbieri and wife Erin Kempe offer his and- her wine lists that range from light rosés to full-bodied cabernets. Barbieri carries cured meats made in San Luis Obispo and artisanal Italian cheeses. 2369 Alamo Pintado Avenue. (805) 688-8882; barbieriwines.com.
During the summer, the family-owned craft brewery Figueroa Mountain Brewing Company hosts Sunday picnics with Santa Maria–style barbecue (bring your own meat) and live music. 2363 Alamo Pintado Avenue. (805) 694-2252; figmtnbrew.com.
Sisters Sunita (pictured) and Anita Stephan at Global Gardens expertly explain olive oil and vinegar origins and pairings at their family’s farm stand, a short drive from downtown. Mom Theo Stephan started the olive oil business in 1998, which has since expanded to include roasted nuts, organic mustards, and beauty products. 2450 Alamo Pintado Road. (800) 307-0447; globalgardensonline.com.
Eat: Sides Hardware and Shoes
When siblings Jeff and Matt Nichols opened Sides in 2012, they wanted to pay homage to the 1901 building’s original tenant, Milburn Sides, who ran a hardware business. Here, instead of tools and screws, you’ll find a thick slab of their award-winning applewood-smoked–bacon steak tucked into their burgers, sandwiches, and even their Bloody Marys.
2375 Alamo Pintado Avenue. (805) 688-4820; brothersrestaurant.com.
Eat: The Bear and Star
An ambitious endeavor from the folks at Fess Parker Wine Country Inn, this restaurant takes the farm-to-table concept up a notch. Most of the food served at the restaurant comes from the nearby Fess Parker Winery’s 714- acre ranch, including rabbit, quail eggs, Wagyu cows, organic vegetables, and heirloom fruit.
2860 Grand Avenue. (800) 446-2455; fessparkerinn.com/dining.