The neon on Fredericksburg Road outlasts the businesses under it. Cool Crest's 1950s hilltop sign now advertises its third set of owners. The Woodlawn Theatre's blade sign hangs over a comedy club. A "Ballroom Bingo" sign that hasn't worked in years stands above a bin store. A former Texaco station on the corridor has a Mexican kitchen in it, which makes it the third restaurant in that building since 2011. All of those changes landed in 2026, within a short walk or drive of Monticello Park.
The Express-News ran a tour of the corridor's signs in late June, written by René Guzman, and noted that most of them "still light the way for their respective businesses still in operation." His neon landmarks feature is the starting point for this route. A fall evening is a good time to drive it, or walk the closer stretch, and see what has changed under each sign.
The Route at a Glance
The stops are listed by street number, heading north on Fredericksburg Road.
| Address | The sign | Under it in 2026 |
|---|---|---|
| 1402 Fredericksburg Rd. | Cool Crest's wavy "World's Finest" hilltop sign, late 1950s | Cool Crest Miniature Golf, under Los Leones since February |
| 1815 Fredericksburg Rd. | An 88-year-old former Texaco station | Con Amor Cocina y Cantina, soft-opened in early September |
| 1920 Fredericksburg Rd. | The Woodlawn's vertical blade sign | Woodlawn Comedy and the 1920 Lounge |
| 2716 Fredericksburg Rd. | Plaza del Rey's "Ballroom Bingo," not working | Bargain$ Depot, opened in May |
| 2814 Fredericksburg Rd. | Two Tip Top signs, both still working | DeWese's Tip Top Café, open since 1938 |
| 4250 Fredericksburg Rd. | Pizza Pete, flipping pizzas | The same Pizza Hut, about 2 miles from where it started |
Cool Crest Has a Third Set of Owners
Cool Crest opened in 1929 with an 18-hole course. Most San Antonians know it from its late 1950s makeover, when Harold and Maria Metzger added a second course, zigzagging white concrete, and the hilltop sign shaped like a putting green that reads "World's Finest" over a globe. The Andry brothers bought the property from the Metzger estate in late 2012 and restored the landmark and its sign, all the way down to the original green paint.
In February 2026 the course passed to Los Leones, the local hospitality group that runs Schilo's and Casa Rio. That makes Los Leones its third owner, according to Axios San Antonio. The course held a grand reopening on Saturday, May 16, with food trucks and live music. A Schilo's food truck now serves tacos and German-inspired items such as schnitzel sliders, bratwurst and pretzels, and the Metzger Biergarten is still open, the Express-News reported. Axios listed Reubens, smash-style sliders, canned Chenin Blanc and Prosecco on tap among the menu changes.
Here are the hours posted on Cool Crest's website as of early October:
- Monday and Tuesday: closed
- Wednesday and Thursday: 4 to 8 p.m.
- Friday: 4 to 9 p.m.
- Saturday: 10 a.m. to 9 p.m.
- Sunday: noon to 6 p.m.
The last tee time is one hour before closing, and hours run later on music Fridays and Saturdays. For now, the site's events section lists no upcoming events.
The new owners have also announced plans to returf the course, bring fish back to the ponds, add a playground, and use holiday lights and art installations around the grounds. These are still plans. If the holiday lights do go up this year, the course will look quite different after dark in December.
An 88-Year-Old Gas Station Gets Its Third Restaurant
About four blocks north, the building at 1815 Fredericksburg Road shows the same pattern of a fixed structure with new tenants. It started as a Texaco station. Deco Pizzeria occupied it from 2011 to 2024, and the burger restaurant Unko Maui's followed. Con Amor Cocina y Cantina began a soft opening there in early September, the Express-News reported.
Con Amor first opened in Highland Park in 2023, at 2314 Steves Ave. It's known there for home-style plates like chile rellenos, gorditas, carne guisada and puffy tacos, plus weekday lunch specials of about $9. The Deco District location has a larger dining room and a patio. The Express-News said it would offer breakfast, lunch and dinner, with hours of 6 a.m. to 10 p.m., seven days a week.
The "Cantina" part of the name hasn't happened yet. In the September 6 report, the restaurant was operating dry, and the owners planned to open the bar at a grand opening once the state approves their liquor license. No later report on that license turned up, so the bar's status is worth checking before you plan around it.
The Woodlawn Sign Now Points to a Comedy Club
Half a mile north of Cool Crest, the Woodlawn Theatre's blade sign marks one of San Antonio's oldest movie houses. The theater opened August 17, 1945, with "National Velvet." John Eberson, the architect of the downtown Majestic, designed it. On October 24, 1960, it hosted the world premiere of John Wayne's "The Alamo," with Wayne in attendance.
The building has changed uses before. It screened films into the early 1980s and then became a general entertainment venue, booking everything from "Jack and the Bean Stalk" to the Red Hot Chili Peppers. Today it is home to Woodlawn Comedy, which describes the theater as a live comedy, music and events venue with a drinks lounge upstairs called the 1920 Lounge. The sign still just says "Woodlawn," so it works for whatever the building is doing.
The venue's site lists these fall and holiday dates:
- Friday, October 16: "Monsternomicon," a live Dungeons & Dragons comedy show
- Saturday, October 24: "A Foreigner's Journey to Boston," a tribute-band show. That's 66 years to the day after "The Alamo" premiered in the same building.
- Friday, October 30: Dr. Vincent Graves' "Condemned"
- Sunday, November 1: "Dia De Los Muertos Spooktacular"
- December 18 through 20: "A Magical Christmas," a family-friendly magic, comedy and music show with illusionist Curt Miller and friends
A Bingo Sign Over a Bin Store, Next to a Diner That Hasn't Changed
The building at 2716 Fredericksburg Road opened in July 1951 as a Handy Andy grocery store, with an Oak Hills Drug and a Fox photo shop as smaller tenants. Handy Andy stayed about 30 years. In the early 1980s the space became Plaza del Rey, hosting wedding receptions and bingo. The "Ballroom Bingo" sign outside no longer works, and RoadsideArchitecture.com estimates it may date to the 1940s or '50s. It has the same Art Deco lines and ring accents as the Woodlawn sign about half a mile away. In May, Bargain$ Depot, a bin and liquidation store, opened in the space.
Across the street, DeWese's Tip Top Café is the one stop on this route where neither the sign nor the business has changed. It has been open since 1938 and still serves the chicken fried steak and onion rings that Pappy and Winnie DeWese first cooked, in the same knotty pine room with the same brown booths. Both of its signs still work. The curbside sign has a marquee with the day's specials, and the "Tip Top" sign over the front door has two pointed T's. Plan your timing, because the restaurant turns them off at closing: 7 p.m. Sunday through Thursday and 9 p.m. on Friday and Saturday. On a weeknight, see Tip Top first and Cool Crest after.
Pizza Pete Moved With His Restaurant
The last stop is in Balcones Heights. Pizza Pete first appeared on the corridor in the late 1960s, outside San Antonio's second Pizza Hut, in the 2500 block of Fredericksburg Road. When the restaurant moved about 2 miles north to 4250 Fredericksburg Road, the sign went with it. RoadsideArchitecture.com estimates the sign was built in 1969 and moved about 30 years later. On this one, the chef's hand moves up and down while the pizza cycles through four positions. Similar Pizza Pete signs showed a single pizza in midair. The location loses points on corporate inspections for its non-conforming sign but can keep it as long as it is maintained.
One more 2026 move on the corridor ran the same direction. Lighthouse Seafood left 1212 Fredericksburg Road in April and reopened at 3534 Fredericksburg Road, the Express-News reported, so it moved without leaving the road.
Back in the Neighborhood for December
Monticello Park has its own version of this pattern. Old buildings stay standing, and the people inside them change over time. The Monticello Park Neighborhood Association's September/October newsletter lists the Holiday Home Tour for December 6, 2026. Eight historic homes in the heart of the neighborhood will be open. The tour is the association's only fundraiser, and proceeds go toward student scholarships, beautification grants, the newsletter and social events. The last tour brought in $10,125, and the first was held in 1995. When the newsletter went out, the committee was still asking homeowners to volunteer houses for the tour. The MPNA Holiday Party follows on December 12.
The same newsletter mentions Bright Coffee and NoFi. It also lists a stitching group that meets every two weeks at Sunset Brews. Woodlawn's Christmas magic show runs December 18 through 20, a week after the neighborhood party, so the two neighborhood events and the Woodlawn shows fill most of December within a few blocks.
The tour homes and the Fredericksburg Road signs show the same thing. Older buildings here keep their character through several owners when each owner looks after what came with the property. If you own one of Monticello Park's historic homes and want to talk through what preserving its character means for a future sale, Patrick Bean is glad to start a conversation.
