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San Antonio Area Roads History
Historical Fredericksburg Rd. Photos

This page last updated April 20, 2018

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Below are historical photos of Fredericksburg Road including the old highway to Boerne and Comfort. These photos were compiled from the TxDOT photo library and the San Antonio TxDOT district office.

Locations are given using the present-day roadway names. The photos are arranged from south to north. Click on each photo for an enlarged view.

Click here to return to the historical photo galleries page.

Route history

SH 9SH 27US 290US 385US 87

The road to Fredericksburg became SH 9 as part of the first state highway system designated in 1917. By the early 1920s, it also became part of SH 27 to Kerrville.

This road was also part of the Old Spanish Trail, a transcontinental auto trail with its headquarters in San Antonio. The section of road between San Antonio and Boerne was known as the "Headquarters Section" and was used to test various road improvements such as pavements, alignments, and safety features and became a model that other localities could emulate.

When the US Highway System was first designated in 1925, this road was numbered US 290, which ran via Comfort to Kerrville and points west. Meanwhile, the road from Comfort to Fredericksburg (SH 9) was numbered US 385. Initially, these routes met in Comfort, but by the late '20s, it appears the route for US 385 was rerouted away from Comfort and instead headed south through Waring and Welfare to meet US 290 at Nelson City, likely to facilitate a more direct route to San Antonio. Although the official southern terminus for US 385 was listed as being at its junction with US 290, it appears that by 1932, US 385 was co-signed with US 290 along the Fredericksburg Road into San Antonio, likely to provide a more logical terminus for the route in San Antonio. In a 1935 revision of the system, US 87 was extended south from Wyoming into Texas and supplanted US 385. At the same time, US 290 was rerouted east from north of Mountain Home through Fredericksburg, Austin, and on to Houston, leaving the segment from Comfort through Kerrville and Mountain Home as SH 27. Finally, a new road from Fredericksburg to Comfort was also completed around that time.

In Bexar County, the route has been fairly stable, running along Fredericksburg Road in San Antonio. Around today's Loop 1604, the route initially used what's now Old Fredericksburg Road; this was bypassed by the current route in the mid '30s.

In Leon Springs, the initial route ran parallel to and just to the east of the road through Leon Springs today (i.e. behind Rudy's). There, it turned left onto Boerne Stage Rd. and followed it northwest to Scenic Loop Rd., then turned north and continued into Kendall County. The route entered Boerne on Old San Antonio Rd. and turned left onto Oak Park Dr. and right onto Main St. and through Boerne. North of Boerne, the route used today's path of I-190 to Nelson City. There, the route curved onto today's FM 289 where SH 9 turned right to Welfare while SH 27 turned left and continued on today's FM 289. It probably then continued on the Old Comfort Road and the High St. Rd. into Comfort.

By the mid '30s, the route through Leon Springs shifted a few hundred feet west (today's main road through Leon Springs) and a new road (today's path for I-10) had been built between Leon Springs and Boerne to replace the route along Scenic Loop Road. Also, a new route between Nelson City and Comfort (also today's I-10) replaced the sections along today's FM 289.

San Antonio's first expressway was built to provide a bypass for US 87 from Fredericksburg at Woodlawn into downtown. Construction of I-10 northward in the early '60s then usurped the section of US 87 on Fredericksburg between Huebner and Woodlawn. Fredericksburg Road west of I-10 was then redesignated SL 345 but was signed as Business US 87 until the early '90s.


Fredericksburg at Cincinnati looking northwest
(ca. 1940/TxDOT)


Fredericksburg at I-10 looking southeast
This was shortly after the expressway opened.
(ca. 1949/TxDOT)


Fredericksburg at I-10 looking northwest
The US 87 expressway ended here at this time. To the right, you can see a ramp curving up from the underpass-- the carried traffic from the expressway onto northbound Fredericksburg Rd. at Magnolia Ave.
(ca. 1950/TxDOT)


Fredericksburg probably at Martinez Creek looking northwest
This photo shows flood damage.
(1921/TxDOT)


Fredericksburg at Donaldson looking southeast
(ca. 1959/TxDOT)


Old Spanish Trail monument at Fredericksburg and Vance Jackson
This monument was placed by the Daughters of the Republic of Texas to commemorate the OST and is still there today!
(ca. 1936/TxDOT)


Fredericksburg at Vance Jackson looking northwest
The monument in the photo above is near the center of this photo.
(1959/TxDOT)


Fredericksburg at Gardina looking northwest
(1959/TxDOT)


Fredericksburg at Gardina looking southeast
(1959/TxDOT)


Fredericksburg at Williamsburg looking southeast
(1959/TxDOT)


Fredericksburg at Balcones Dr./Spencer Ln. looking northwest
(1959/TxDOT)


Fredericksburg in Balcones Heights looking southeast
(1959/TxDOT)


Fredericksburg near Oaklawn looking northwest
Today's Callaghan Rd. crosses near the middle of this photo.
(1921/TxDOT)


Fredericksburg Road - Location unknown
(1921/TxDOT)


Fredericksburg Road - Location unknown
(1921/TxDOT)


Fredericksburg Road - Location unknown
This is the highway somewhere between San Antonio and Boerne.
(ca. 1935/TxDOT)


Main Street bridge in Boerne probably looking east
Photo shows flooding in progress on Cibolo Creek.
(ca. 1935/TxDOT)


US 87 bridge over Guadalupe River south of Comfort probably looking northwest
This bridge has since been replaced.
(ca. 1935/TxDOT)


Business US 87 and Ave. A in Comfort looking south
At this time, this was the junction of US 87, SH 9, and SH 27. The right fork was SH 27 to Kerrville while the left fork was US 87 and SH 9 to San Antonio. The building in the middle was a gas station and still exists today.
(ca. 1935/TxDOT)



Click here to return to the historical photo galleries page.




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