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Old Town, Uptown, & Mission Valley : Overview & Top 10

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This long stretch follows the San Diego River from the Mission San Diego de Alcalá to Old Town. Over 200 years ago, Kumeyaay Indians lived in tribal groups within small settlements in the valley. Unknown to them, strangers from the other side of the earth would change their lives forever. Spanish soldiers and Franciscan padres would have their time of glory here, as well as San Diego’s pioneer families. Today, the valley itself holds little interest beyond masses of chain motels and shopping centers intersected by a freeway; however, on the bluffs above, you’ll find eclectic neighborhoods overflowing with charm, brilliant architecture, and chic restaurants. Tolerance and diversity creates a progressive, Bohemian air, while rising real estate prices have turned simple bungalow homes into showpieces. And San Diego’s birthplace is always close by.

  • Morning

    Begin at the Old Town Transportation Center. Cross the street and follow the path into Old Town State Historic Park. Just to the left is the Visitor’s Center, where you can pick up a map. Walk along the right side of the Plaza and peek into the U.S. Apothecary Shoppe. Follow the signs to the Casa de Machado-Stewart and the Mason Street School (see Mason Street School). Back at the Plaza, visit the La Casa de Estudillo (see La Casa de Estudillo) for the best insight into an upper-class home of early California. From the Plaza’s southwest corner, continue out of the State Park. Walk along San Diego Avenue, where you’ll find souvenir shops, galleries, and restaurants. Try the Old Town Mexican Café (see Old Town Mexican Café & Cantina) for lunch.

    Afternoon

    Cross the street at Conde and backtrack up San Diego Avenue to visit the haunted Whaley House. Turn right on Harney Street and walk uphill to Heritage Park. Backtrack one block to the Mormon Battalion Visitor’s Center. Turn right on Juan Street and walk to Mason. You’ll see a sign indicating “The Old Presidio Historic Trail”. Turn right on Mason, follow the golf course to Jackson, and look for the footpath across the street. You’ll parallel Jackson to the left and wind uphill to Presidio Park. Across the grass are the ruins of the original presidio, the Serra Cross, and the Serra Museum.

  • Still untouched by San Diego’s urban renewal boom, antique stores, second-hand book and record shops, and retro-clothing boutiques are sprinkled along these streets in east Hillcrest and Normal Heights.

  • Find a wacky item to make you the life of the party. Flashing “Kiss Me” buttons, guns that launch plastic pigs, Wonder Woman memorabilia, and Tikis are the favorites.

  • Lining a lushly landscaped plaza decorated in brilliant colors, quality shops offer Mexican tableware, folk art, Guatemalan textiles, and books (see Bazaar del Mundo).

  • Breads such as anise and black-olive loaf are baked and made into unusual sandwiches.

  • Head to this quiet bungalow for an elegant seafood dinner. Try the signature drink, a Pomerita.

  • Seniors and budget-eaters love the hearty food here. Mashed potatoes and gravy accompany tasty chicken pies.

  • The excellent, authentic Mexican cooking includes mole poblano , a traditional sauce that combines chilies and chocolate served with meat dishes.

  • Discover decorating ideas among the exotic home accents, antiques, and teak furniture, mostly from China and Southeast Asia. Planters and patio decor fill the outside.

  • Corvette Diner

    Cruise back to the 1950s in this diner decorated with hub-caps, vintage gas station signs, and a yellow Corvette.

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