This long stretch follows the San Diego River from the Mission San Diego de Alcalá to Old Town. For as long as 12,000 years, the Kumeyaay tribe lived in small settlements in the valley, unaware that strangers from the other side of the earth would change their lives forever. Both Spanish soldiers and Franciscan padres had glory here, as well as San Diego’s pioneer families. 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.


1. Old Town State Historic Park

San Diego’s first commercial settlement has been either preserved or re-created in this pedestrian-only park. Much of the town was destroyed in a fire in 1872, prompting the development of a new town center closer to the water, but several original structures remain. You can wander into any of Old Town’s houses and find museums or concession shops inside.

2. Junípero Serra Museum

prac_info 2727 Presidio Dr • 619 232 6203 • Open Jun–Sep 4: 10am–5pm Tue–Sun; Sep 5–May: 10am–4pm Sat & Sun • Adm • www.sandiegohistory.org

Constructed in 1929 to a design by William Templeton Johnson, the museum building is in keeping with the city’s Spanish-Colonial heritage. Its white stucco arches, narrow passages, red-tile roof, and stately tower pay tribute to the first mission, which stood near this site. Artifacts from ongoing archeological excavations, ceramics made by the Kumeyaay tribe, clothing, furniture, and a cannon help illustrate the meager life people led. Climb the tower to compare today’s view with that of 1929.

3. University of San Diego

prac_info 5998 Alcalá Park • 619 260 4600

Grand Spanish Renaissance buildings distinguish this independent Catholic university, its design inspired by the university in the Spanish town of Alcalá de Henares. Of exceptional note is the Founders Chapel with its white marble altar, gold-leaf decoration, 14 stained-glass nave windows, and marble floor.


University of San Diego

4. Mission Basilica San Diego de Alcalá

A peaceful enclave among the nondescript strip malls of Mission Valley, the mission’s original spirit still lingers in the church and its lovely gardens. The first of California’s 21 missions was moved to this permanent site a few years after its founding. Over the years, the structure was rebuilt to suit the needs of the time. Its famous facade and bell tower have inspired architects to copy the “Mission Style” throughout San Diego.

5. Mission Hills

prac_info Mission Hills Nursery: 1525 Fort Stockton Dr

One of San Diego’s most charming and romantic neighborhoods is in the hills overlooking Old Town and San Diego Bay. Tree-lined streets run past architectural jewels built in various styles. Dating from the early 1900s, homes had to cost at least $3,500, and could not keep any male farm animals. Only those of Caucasian descent could hold property. Kate Sessions’ 1910 nursery (see The Mother of Balboa Park) can still be visited here.

6. Whaley House Museum

prac_info 2482 San Diego Ave • 619 297 7511 • Open 10am–4:30pm Sun–Tue, 10am–9:30pm Thu–Sat; late May–early Sep: 10am–9:30pm daily • Adm • whaleyhouse.org

California’s first two-story brick structure also served as San Diego’s first courthouse, county seat, and home to Thomas Whaley, who built it in 1856 over a graveyard and site of a former gallows. The US Commerce Department declared the house officially haunted in the 1960s.


Interior of haunted Whaley House

7. Hillcrest

Considered San Diego’s first suburb in the 1920s, Hillcrest slowly developed into a residential area, offering a quiet alternative to the bustle of downtown. A trolley stop opened the neighborhood up to thriving businesses, restaurants, and theaters; in the 1940s, merchants proudly erected a sign that spanned University Boulevard, proclaiming “Hillcrest” to the world. But fortunes changed, neglect followed, and this sign came down. In the 1970s, the LGBT+ community took up the revitalization challenge and transformed the community into a hip destination with great restaurants, nightlife, and avant-garde shops. And now the sign is back – in neon.

8. Presidio Park

The Kumeyaay tribe once used this hillside for sacred ceremonies. Site of the original Spanish presidio and mission settlement, a lovely park is all that’s left of San Diego’s beginnings. The park contains the Junípero Serra Museum and the remaining earthen walls of Fort Stockton, a fortress that changed hands several times during the Mexican-American War, marked by bronze monuments, a flagpole, and a cannon. The 28-ft (8.5-m) Serra Cross, constructed from mission tiles, honors founder Saint Junípero Serra.

9. Mormon Battalion Memorial Visitor’s Center

prac_info 2510 Juan St • 619 298 3317 • Open 9am–9pm daily

In July 1846, 500 men, 32 women, and 51 children set out from Council Bluffs, Iowa, on what would be considered one of the longest military marches in history. Six months and 2,000 miles (3,218 km) later, they reached San Diego to support the American military garrison in the Mexican-American War. At the Visitor’s Center, a volunteer from the Church of Latter-Day Saints discusses the march and Mormon contributions to the area.


Mormon Battalion Memorial

10. Heritage Park

prac_info County 2454 Heritage Park Row • 619 819 6009 • Open 9am–5pm daily

Downtown’s rapid expansion after World War II almost destroyed several Victorian heritage houses and San Diego’s first synagogue. The Save Our Heritage Organization rescued and moved these architectural treasures to this specially created park. Of notable interest is the Sherman Gilbert House, once home to art and music patrons Bess and Gertrude Gilbert, who hosted luminaries such as Artur Rubinstein, Anna Pavlova, and the Trapp Family Singers.


Houses in Heritage Park


In 1800, Apolinaria Lorenzana and 20 orphans arrived from Mexico to be distributed to respectable presidio families. She taught herself to write by copying every written thing she found. She spent her life caring for the mission padres, teaching children and women church doctrine, and tending the sick. Nicknamed La Beata, she was one of the few women to receive a land grant.




Begin at the Old Town Transit Center. Cross the street and follow the path into Old Town State Historic Park. Just to the left is the Interpretive Center, where you can pick up a map. Walk along the right side of the Plaza and peek into the Bailey & McGuire Pottery Shop. Follow the signs to La Casa de Machado y Stewart and the Mason Street School. Back at the Plaza, visit 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 for lunch.


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 Serra Cross, the original presidio, and the Junípero Serra Museum.


1. Bazaar del Mundo

prac_info 4133 Taylor St • 619 296 3161

In a lushly landscaped plaza, quality shops offer Mexican tableware, folk art, Guatemalan textiles, and books.

2. Gioia’s Room

prac_info 3739 6th Ave • 619 269 2303

An interesting boutique that offers accessories and vintage women’s clothing with free alterations.

3. Old Town Market

prac_info 4010 Twiggs St • 619 260 1078

This festive market offers entertainment and local artisans. The shops sell colorful Mexican goods, such as Day of the Dead folk art, as well as jewelry and gifts.


Mexican crucifixes, Old Town Market

4. Four Winds Trading Company

prac_info 2448-B San Diego Ave • 619 692 0466

This Old Town store specializes in authentic Native American pottery, weavings, jewelry, dreamcatchers, and paintings of Native American themes.

5. Record City

prac_info 3757 6th Ave • 619 291 5313

There’s nothing quite like vinyl, and the crates here are stocked with rock and 1980s and 1990s alternative music. Used CDs are also on sale.

6. Thread & Seed

prac_info 2870 4th Ave • 619 994 1425

This small, tidy and elegant shop features luxe bath products, cosmetics, candles, chocolates, books and jewelry. Their custom gift boxes are a specialty.

7. Creative Crossroads

prac_info 502 University Ave • 800 685 2513

Local artisans show and sell their wares in this marketplace near the corner of University and Fifth. Purchase jewelry, greeting cards, art, gifts, and Gay Pride apparel.

8. Bluestocking Books

prac_info 3817 5th Ave • 619 296 1424

This independent store offers new and used books on a wide range of subjects. The search service aims to locate rare and vintage items.

9. Whole Foods

prac_info 711 University Ave • 619 294 2800

With an emphasis on fresh organic food, you’ll find flavorful produce, a great assortment of imported goods, and a deli that specializes in healthy takeout.

10. Fashion Valley

prac_info 7007 Friars Rd • 619 297 3381

From Neiman Marcus and Nordstrom to Apple, Gucci, and Tiffany, this two-level, open-air mall (see Fashion Valley) has more than 200 stores. There are also many great food outlets and an 18-screen theater. The mall closes at 9pm every night.

Places to Eat

1. Jack and Giulio’s Italian Restaurant

prac_info 2391 San Diego Ave • 619 294 2074 • $$

Classics like Caprese salad, scampi, as well as tiramisu are served in a romantic and intimate space – a welcome respite from the crowds in Old Town.

2. Saffron

prac_info 3731 India St • 619 574 7737 • $

Parking is tricky, but crowds come here for wondrously flavorful Thai cuisine. Takeout is also available.


Thai dishes are served up at Saffron

3. El Agave Tequileria

prac_info 2304 San Diego Ave • 619 220 0692 • $$

Utter culinary magic awaits within one of the first tequilarias in San Diego. Classic Mexican food with modern touches.

4. Crest Café

prac_info 425 Robinson Ave • 619 295 2510 • $

Locals love this upscale diner, serving fresh soups, salads, and big burgers.


Dessert at Crest Café

5. Arrivederci Ristorante

prac_info 3845 4th Ave • 619 299 6282 • $$

Service at this cozy spot is friendly, prices are reasonable, and the pasta dishes are some of the best in town.

6. Blue Water Seafood Market & Grill

prac_info 3667 India St • 619 497 0914 • $

A fabulous selection of seafood is on offer at this friendly seafood market. Try the fish tacos, seafood cocktails, or chowders.

7. Bertrand at Mr. A’s

prac_info 2550 5th Ave, 12th Floor • 619 239 1377 • $$

Popular choices at Bertrand at Mr. A’s include sautéed Alaskan halibut with scallops and a trio of scrumptious vegetarian creations.

8. Casa Guadalajara

prac_info 4105 Taylor St • 619 295 5111 • $$

This festive restaurant is a grand celebration of Mexican specialties and premium margaritas, along with folk art, fountains, and mariachis.

9. Brooklyn Girl Eatery

prac_info 4033 Goldfinch St • 619 296 4600 • $$

Savor seasonal menus with locally sourced products. Try the bacon-wrapped Vietnamese meatballs.

10. San Diego Chicken Pie Shop

prac_info 2633 El Cajon, North Park • 619 295 0156 • No credit cards • $

Seniors and budget-eaters love the hearty food here: think tasty chicken pies accompanied by mashed potatoes and gravy.

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