You’ve likely heard someone say they “miss the old San Antonio.” It’s no secret that we’ve lost beloved restaurants and businesses that shaped our city over the years.

Still, there are local spots where the Alamo City feels frozen in time, if you know where to find them. From old-school eateries to century-old retailers, these establishments are living pieces of San Antonio’s history.

1910s

1916 |Penner’s, 311 W. Commerce St.
What began as a second-hand shop in the early 1900s has grown into one of San Antonio’s most iconic men’s clothiers. While its offerings have evolved over the years, the store has stayed true to its commitment to top-notch service and complimentary in-store custom tailoring.

This local fixture has served German-Texan fare for 108 years. | Photo by Joseph via Openverse

1917 |Schilo’s Delicatessen, 424 E. Commerce St.
San Antonio’s oldest restaurant started in Beeville, Texas, when “Papa” Fritz Schilo opened a saloon in the early 1900s. After relocating to San Antonio, his wife began serving her German recipes to saloon guests. The restaurant has called its current spot — a former currency exchange bank — home since 1942. Fun fact: Its original bank vault now serves as a walk-in cooler.

1917 | Paris Hatters, 119 Broadway
This world-famous, century-old shop’s clientele list features notable names like Bob Dylan, Paul McCartney, President Harry Truman, Waylon Jennings, and Pope John Paul II. Pro tip: When you go to check out, admire its cash register from the 1930s that requires hand-cranking to open.

1930s

1932 | Golden Star Cafe, 821 W. Commerce St.
Golden Star Cafe’s story began when Grandpa “Papa” Lim immigrated to the US from China and began serving his scratch-made pies. A look through the family-owned cafe’s archives reveal its rich history, while a glance at its menu demonstrates how it’s kept diners coming back for nine decades.

1932 | La Fonda on Main, 4215 N. Main Ave.
Touted as “San Antonio’s oldest Mexican restaurant,” this modern-day hotspot for happy hour deals on the patio began when two sisters transformed their 1921 home into a full-service restaurant.

1935 | The Broadway 5050, 5050 Broadway, Alamo Heights
Once an ice cream parlor and speakeasy, this longtime Alamo Heights spot now serves the “best cheeseburger in San Antonio.” Founded by the Montanio family, “The 50” has changed hands several times over the years. Psst — stop in on Thursdays for trivia and Saturdays for karaoke.

1940s

1941 | Mi Tierra Cafe y Panaderia, 218 Produce Row
Mi Tierra Cafe began as a three-table restaurant at San Antonio’s Mercado geared toward early-rising farmers. Its famous Mexican pastries were introduced in 1955, and the rest is history.

Take a stroll along the San Antonio Riverwalk. | Photo by fs_photographic.

1946 | Casa Rio, 430 E. Commerce St.
“Old” San Antonio is alive and well at this River Walk landmark. Take your taste buds back in time by ordering the original plate, a dish from its first menu that comes with a tamale, enchilada, chili, rice, and beans.

1950s

1954 | The Original Donut Shop, 3307 Fredericksburg Rd.
Donuts or tacos? Don’t let the name fool you — you can have both at this tried-and-true establishment. Founder Patrick Morris debuted the restaurant as “Hot Donuts” in 1954 before introducing tacos to its menu and changing its moniker in the early 1980s.

Follow the neon glow to the puffy tacos. | Photo by Wally Gobetz

1956 | Ray’s Drive Inn, 822 Southwest 19th St.
Raymond Lopez started Ray’s Drive Inn by showing free films at his family’s grocery store and serving concessions like hamburgers, fried chicken, hand-squeezed lemonade, and cold beer. Today, it’s trademarked as the “home of the original puffy taco” and sells 500+ each day.

We’ll add more decades + local businesses over time — let us know which San Antonio establishment you’d like to see on the list.