Greatest Hits: San Antonio Restaurants That Have Stood the Test of Time

San Antonio’s restaurants can be measured in many ways, from the number of awards they’ve won to the role they've played in putting the city on the culinary map. But, given our city’s propensity for nostalgia, plenty of residents also take note of how long restaurants have been a part of the local food scene. These establishments have all stood the test of time, each having served San Antonians for 60-plus years.

Schilo’s Delicatessen (1914)

As the city’s oldest continuously operated restaurant, Schilo’s Delicatessen is packed with history. The deli actually began as a saloon in Beeville in 1900 before founder Fritz Schilo moved it to downtown San Antonio in 1914. German dishes made their debut three years later, allowing customers to pair beer with the sausage of their choice. Today, those sausages and other German basics pair well with a frosty mug of Schilo’s homemade root beer. 424 E. Commerce St., (210) 223-6692, schilos.com.

San Antonio Pig Stand (1927)
Pig Stands popped up all over Texas in the 1920s and 1930s, but the only one still operating in the Alamo City can be found on Broadway, the sign still immortalizing the diner’s signature menu item, the pig sandwich. SA’s Pig Stand was set to close in 2005, until waitress-turned-manager Mary Ann Hill stepped up to keep the doors open. 1508 Broadway, (210) 222-9923, sanantoniospigstand.com.

Grey Moss Inn (1929)
San Antonians know the 90-year-old Grey Moss Inn as a destination for fine dining in a romantic setting. You can bet that steaks, seafood and other signature dishes will be served up with a history lesson. Tales of hauntings are also part of that history, or so say the ghost tours that take place on the grounds. 19010 Scenic Loop Rd., Helotes, (210) 695-8301, grey-moss-inn.com.

La Fonda on Main (1932)
Inside La Fonda’s recognizable white stucco building you’ll find casual fine dining and warm hospitality – such has been the case since the restaurant’s 1932 debut. Both familiar Tex-Mex fare and an extensive menu of dishes from Mexico’s interior have kept San Antonians coming back for decades. Alicia Guadiana, the unofficial face of the restaurant, worked at La Fonda on Main for 53 years before passing away in 2017. 2415 N. Main Ave., (210) 733-0621, lafondaonmain.com.

Earl Abel’s (1933)
Despite a relocation from its classic Broadway outpost, this Alamo Heights mainstay has managed to keep its doors open since 1933. Restaurant founder Earl Abel needed a way to provide for his family during the Great Depression, so he opened up his own diner. He waited out a slow start, hustled to make things work and eventually opened five additional locations (all closed during World War II due to labor shortages). Sure, the 2019 Earl Abel’s is far different from the one of last century, but like its founder, it on keeps on trucking. 1639 Broadway, (210) 822-3358, earlabelssa.com.

Teka Molino (1937)

Teka Molino, one of the city’s oldest Tex-Mex eateries is known for its puffy tacos, bean cups and fried cheese tacos. The success of its San Pedro outpost led to a second location on Rittiman Road. The family-run operation prides itself on using ingredients prepared “by our family, for your family.” Throw in quick, friendly service plus affordable prices, and you’ll see why so many locals love this puro-as-hell mainstay. Multiple locations, tekamolino.com.

De Wese’s Tip Top Cafe (1938)

Since opening its doors in 1938, De Wese’s Tip Top Cafe has served up timeless favorites that have won the hearts of locals and tourists alike. Prized for diner eats like Texas-sized chicken fried steaks and golden onion rings, Tip Top has gained notoriety as a destination that proves everything is bigger in Texas. Resist the urge to finish the gargantuan portions and save room for dessert so you can enjoy a slice of pie that’s made fresh daily. 2814 Fredericksburg Rd., (210) 732-0191, facebook.com/tiptopcafesanantonio.

Hung Fong Chinese Restaurant (1939)
Calling itself the oldest Chinese restaurant in Texas, Hung Fong is a longtime resident of the ever-changing Broadway corridor. Over its 80 years in business, the family-owned dining spot has earned its place as a go-to for Chinese-American dishes like sesame chicken and egg foo yung. Come for the food and stay for the decor, which includes two neon flags — representing the two cultures of the U.S. and China — on the ceiling. Fun fact: the flags were installed before Alaska and Hawaii joined the U.S., so there are only 48 stars on the American flag. The success of the Broadway mainstay led to the 1983 opening of sister restaurant Ding How. 3624 Broadway, (210) 822-9211, hungfongsa.com.

Broadway 5050 (1927)
A grease fire took out the kitchen a few years ago and a reopening looked unlikely, but this popular Alamo Heights watering hole came back strong — and with a facelift. The 5050 continues to pack in the crowds for booze and burgers. Its refillable B-Fiddy Fiddy glasses were popular back in the day and its happy hour drink specials still are. Plus, it boasts a menu of cut-above bar food inspired by Quentin Tarantino’s Reservoir Dogs and Pulp Fiction. 5050 Broadway, Alamo Heights, (210) 832-0050, broadway5050.com.

Mi Tierra (1941)

While Mi Tierra’s sprawling interior and flashy decor have defined the downtown restaurant for years, it had far more humble beginnings. Founders Pedro and Cruz Cortez opened it as a three-table cafe in 1941, serving farmers and mercado workers in the early hours. Today, Mi Tierra is a destination for tourists and an after-hours stop for locals. The restaurant is still run by the Cortez family, though, including esteemed chef Cariño Cortez. 218 Produce Row, (210) 239-9215, mitierracafe.com.

Casa Rio (1946)
Alfred F. Beyer opened Caso Rio during the development boom that scattered restaurants and shops along the River Walk during its development. History buffs will appreciate that the Tex-Mex eatery sits on land granted in a title by the King of Spain. And the building itself — from its fireplace and cedar door to its thick rock walls — certainly suggests a rich past. Not to mention, it’s got a fine view when you’re enjoying a margarita or two. 430 E. Commerce St., (210) 225-6718, casa-rio.com.

Jacala Mexican Restaurant (1949)
Rudolph and Adel Quiñones originally opened this near-North Side restaurant in a tiny building (hence the “jacala” part of the name, which translates to small hut). Rudolph was the kitchen wiz who perfected the restaurant’s signature enchiladas, while Adel was the friendly face of the operation. As fans became regulars, the couple added more dining space. Today, San Antonians can choose from Jacala’s dining rooms, patio or the outdoor courtyard to enjoy its prized enchiladas. 606 West Ave., (210) 732-5222, jacala.com.

Luther’s Cafe (1949)
Part of San Antonio’s landscape for 70 years, Luther’s is all about classic Texas-style hamburgers, homemade stew and classic chili con carne. With a location in the heart of the Tobin Hill neighborhood, Luther’s has also become mainstay for the LGBT community, both as a dining establishment and as a spot to hit up for entertainment including live music and drag shows. Though known for being gay-friendly, Luther’s is an institution that welcomes all. 1503 N. Main Ave., (210) 223-7727, lutherscafe.com.

Bun N’ Barrel (1950)

Operating in the Alamo City since 1950, Bun N’ Barrel is all about keeping it old school. The Austin Highway landmark offers barbecue classics like pork ribs and sausage as well as favorites like the Terrace Burger and rich and smooth milkshakes. The longstanding eatery even got a visit from Guy Fieri as part of his Food Network show Diners, Drive-Ins and Dives. Spot the iconic neon sign and pull over to try the brisket sandwich (or whatever entices you) if you want to see what the fuss is about. 1150 Austin Hwy., (210) 828-2829, bunnbarrel.com.

Original Donut Shop (1954)
Is it a donut shop? Or is it a taco stop? It’s both — and does them well. Although the Original Donut Shop has let San Antonians satisfy sweet cravings since 1954, tacos didn’t made their debut until the early 1990s. Long lines form most weekends, often spilling out onto Fredericksburg Road. Last October, the Deco District icon dropped its strict cash-only rule and began accepting credit cards. Even so, whether you come for the donuts and stay for the tacos or vice versa, you’re almost always guaranteed a wait. But the food’s worth it. 3307 Fredericksburg Road, (210) 734-5661, facebook.com/theoriginaldonutshop.

Ray’s Drive Inn (1956)
For more than 60 years, Ray’s Drive Inn has stood proud as a West Side landmark known for its puffy tacos. Raymond Lopez opened the puro dining spot in 1956, offering free movies for neighborhood families and hosting live bands on weekends. In 1982, his brother Arturo purchased the restaurant with the stipulation that its name would remain the same. Ten years later, Arturo received a trademark for first creating the “puffy taco,” and it still churns out more than 500 of the pillowy San Antonio staples daily. Though Arturo has since passed away, the legacy of Ray’s and the entire Lopez family lives on. 822 SW 19th St., (210) 432-7171, raysdriveinn.net.

Mexican Manhattan (1958)

Tony Karam opened this longtime River Walk favorite after serving in the Navy during World War II, at first offering free meals to diners in exchange for feedback to perfect its recipes. Over generations, the Karam family has kept the focus on delivering fast and friendly service in a relaxing atmosphere — even as the restaurant undertook multiple expansions to serve its growing clientele. With views to complete the dining experience, Mexican Manhattan remains a destination for San Antonians old and new. 110 Soledad St, (210) 223-3913, mexicanmanhattan.com.