Exxon / 4282 TX-21 "Bubba's Travel Stop & Country Store" is the "new Exxon" here. I believe it opened in late 2019.
The Country Store / 4293 TX-21
"The Country Store" is much older and advertised Diamond A Ranch Beef on the old Exxon corridor. It is a gas station and convenience store and it seemingly ceased selling gas sometime in 2004-2005 based on non-functional signage, but it seems to have simply not bothered updating the signage anymore. Nevertheless, the Exxon signage and pumps remained up for the next decade despite its dilipidated state. It has been here since the mid-1990s (at least) though the canopy was smaller originally.
Shell / 4360 West TX-21
There's one more gas station (a Texaco) before you hit this Caldwell area gas station. Currently known as "Caldwell Truck & Food Stop" (it was "Big's" convenience store from the early 2000s until sometime around 2016, the name change brought a Krispy Krunchy fried chicken program), and has been here since at least the late 1980s, though not necessarily under those names (it has been a Shell since at least 2003, and likely a Texaco before that) or size (the gas canopy has been enlarged with a second truck-oriented one built later, these improvements came in line between 1998 and 2002).
This started as "Countryside Grocery & Pub" (I found and commented it on Vintage Aerial) in 1984, the name changed in 2005. I think the Texaco name might've come in during the late 1990s/early 2000s improvements.
Triple M Storage / 530 County Road 102
Originally "All American Storage" when it opened between February 2008 and May 2009, sometime between 2013 and 2016, an additional building was built, and it assumed its current name with new management.
Pico Propane and Fuels / 2080 W. State Highway 21
In 2015, the building included Celebration Church and J&J Tire Service, by 2016 it was Celebration Church exclusively, and in 2017 it was Flipz Cheer & Tumble, a cheerleading/gymnastics facility for girls 3-18.
Pico has done more than just occupy it, there's a large fenced-off propane tank near the parking area now.
Rockin' G Oil Company / 1515 W. State Highway 21
This large gas station and convenience opened in August 2015. It features "Papa G's" hamburger stand and "Nonnie's Bakery" which is open in the morning. (If you missed the morning hours, there's usually leftovers sold in the convenience store).
Americas Best Value Inn / 1108 Highway 21 West
In 1976, Leisure Lodge Nursing Home opened in Caldwell at 701 North Broadway Street. In the late 1990s, it switched to Caldwell Health and Rehabilitation Center and shut down in 1999. After sitting vacant for a decade, it sat vacant for over a decade until it opened sometime around early 2011 (best I can tell, possibly opened in late 2010) as Americas Best Value Inn Caldwell.
JLyle Medical Clinic & Gallery / 501 N. Stone Street
This medical clinic is located at the corner of Stone Street and Highway 21, right about where Highway 21 descends below the railroad tracks. The combination medical clinic/art gallery is an homage to the late Dr. Carlyle Smith's passion for sculpting, whose art still litters the yard of the converted house. There's an entry on Roadside America. The most memorable one is the one featuring the head of a construction worker on the head of a bird (at least that's my opinion).
Groce Service Station / 507 Highway 21 West
I believe these may have been a Texaco prior to 2003 but for a decade following was a Shell, featuring a garage instead of a convenience store (it also had a car wash). In 2012, a new canopy (not in Shell colors), a truck/diesel canopy was built in front of the car wash. In spring 2017, it became "Rockin' G Service Center" (associated with the main gas station up the road) but by 2019 changed names again.
500 Highway 21 West
This oft-empty building was Burleson County True Value Farm & Home Supply in the late 1980s and early 1990s (I'm not sure what it has served as since or before).
In the mid-to-late 2010s it was used a daycare (Learning Station), which then became "Blessings from Above Daycare #2"; the "original" was (at the time) near the corner of Holleman and Anderson in College Station. At the time they had labeled the business as 600 W. State Highway 21 but it's actually in the 500 block.
Dollar General / 403 West Highway 21
Dollar General has been in Caldwell since the early 1990s but moved here in 1995. It doesn't look like it anymore since the new logo was installed, but it had, prior to this, the 1984 logo, which had "Dollar" on the left and "General Stores" on the right side. Most of the other stores I was familiar with used the 1995 or 2009 logo. You can see it on the older Street View here.
Dollar Tree / 400 West State Highway 21
This opened as a Family Dollar (#09042) in spring 2012 but sometime in 2018 or 2019 it was converted to a Dollar Tree.
Area 3:16 / 104 West State Highway 21
This church is located in a building that from the late 1970s to around 2008, it was J&H Food Market, which included a meat counter. In the 2010s it was converted to a church, and by 2018 completed an expansion.
Shell / 100 East State Highway 21
This Shell has been here for years (long pre-dating 2003) and has a Zip'N-branded convenience store.
Sunny Donuts / 203 E. Highway 21
Until around the end of 2016, this site (203 Texas 21) was Kolache Capital Bake Shop, located a town that advertises itself as the "Kolache Capital of Texas" (even an annual festival), but it moved to downtown Bryan, about 25 miles away. It is now a donut shop, though it didn't open until around September 2017.
McDonald's / 303 N. Green Street
This McDonald's with a Playplace was only opened in 2001...a shock to me when I was researching it because I seem to remember it being there much longer. (Guess not). It's in a bit of an odd location, despite being at the corner of Highways 21 and 36, the exit to the restaurant dumps you directly onto the slip ramp to southbound Highway 36. In fall 2011 the restaurant renovated to the chain's current prototype.
If you continue south on Highway 36 it eventually turns into Highway 290 which goes into Houston as Northwest Freeway.
Surrey Inn & Restaurant / 403 Highway 21 East
The Surrey Inn has been around as long as I can remember, and indeed—Burleson CAD indicates it was built back in 1965. It has a detached restaurant that based on some filings I've seen changes menus and formats every so often are brief closures, though it still seems to draw a consistent following and always has chicken fried steak on the menu.
Whataburger / 306 N. Wright Street
Whataburger (#1183) opened a location in Caldwell in March 2021. By May 2022 the ground immediately west to the Whataburger was being ripped up for a 7-Eleven. After this, there's not much more of Caldwell heading east, there's a Tractor Supply Company and another gas station but that's just about it. Cooks Point is farther down, their Exxon station is currently being rebuilt as of this writing.
Royalty Pecan Farms / 10600 State Highway 21 East
One of the things seen heading out of town (the warehouse has the best visibility from the west) is Royalty Pecan Farms. The address apparently used to be 10740 State Highway 21 and was established in 1993. Later on (around 2009) they established a retail store and started doing tours and weddings.
Going further east is a large steel bridge where the railroad crosses the Brazos River parallel to Highway 21. There's some fencing along the main railroad structure that wasn't always there. I seems to recall this was installed in the 2000s not longer after a drunk college student fell off the bridge and became a paraplegic. The railroad here isn't even the same railroad that heads west out of Bryan, both lines head north and merge at Mumford.
Highway 21 continues into Bryan here.
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