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Union Street

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History: Cow Hollow was once a pastoral landscape of vegetable gardens and cattle-grazing land that produced food for the city. The cows themselves were banished from the district in 1891 to address public health concerns, but the name stuck. As settlers began flocking to San Francisco, this stretch of neighborhood between the budding downtown and the Presidio became a verdant home for the wealthy, who built grand and colorful Victorians on the steep hillsides. Because the area was largely spared in the 1906 earthquake, it makes for a fantastic afternoon of wandering for architecture buffs (don’t miss the Octagon House on Gough Street, built in 1861-yes, it has eight sides). The neighborhood is all about preserving a slice of the past and favoring small, locally owned and operated businesses. Even as the shopping district along Union Street has grown to include some premium national brand names, several historic buildings have been preserved and restored. Every year, the shops join together for a June street festival offering food stalls, crafts, and live music, as well as a super sidewalk sale in July with specials and bargains.

Don’t Miss: This neighborhood is known as much for its young and well-groomed residents as for its pristine appearance. To discover for yourself where they outfit themselves, stroll along Union Street and scope out the cool salons, jewelry and apparel shops, galleries, and home decor stores. If you’re the type who likes to sweat, gear up at the new Nike Women’s store and check out the full-body indoor cycling classes at nearby SoulCycle. For a cardiac challenge, head to the western edge of the neighborhood to the Lyon Street steps, adjacent to the Presidio- the view from the top of the Marin Headlands is worth the effort, though you’ll no doubt share the flights with other exercisers and even a few bootcamp classes. Once you’ve summited the stairs, regain those burned calories by taking advantage of one of the neighborhood’s seemingly endless refueling options. Among the best choices are Gamine (a French neighborhood bistro serving classics such as escargot and steamed mussels) and Roam Artisan Burgers. Come nightfall, the streets are hopping with nightlife. The so-called Bermuda Triangle marks the center of the scene at Greenwich and Fillmore Streets, though more leisurely pubs and bars along Union Street, like Perry’s and the Bus Stop Saloon, have their charms.