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San Antonio Area Roads History
Historical Fredericksburg Rd. Photos

This page last updated September 18, 2018


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 ran through Waring and Welfare to meet US 290 at Nelson City (where PoPo's is), 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 for US 87 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 first road ran parallel to and just to the east of the main road through Leon Springs today (i.e. that little road behind Rudy's.) Prior to the state highway system, one route from Leon Springs to Boerne continued along what's now Old Fredericksburg Road northward. However, it appears the initial state highway turned left onto Boerne Stage Rd. and followed it northwest and then curved north onto Scenic Loop Rd. and continued into Kendall County. The route entered Boerne on Old San Antonio Rd. and curved left onto Oak Park Dr. and right onto Main St. through Boerne. North of Boerne, the route crossed back and forth on today's I-10 right-of-way to Nelson City. There, the route curved onto today's FM 289 and onto the Waring-Welfare Rd. to the T intersection at Green Cedar Rd. There, SH 9 turned right to Welfare while SH 27 turned left and continued mostly on today's FM 289, Old Comfort Road, and High Street Rd., before crossing the Guadalupe River on the High St. bridge into Comfort.

By the mid '30s, the route through Leon Springs shifted a couple hundred feet west (today's main road through Leon Springs) where it continued north-northwest on a new road (today's path for I-10) that had been built between Leon Springs and Boerne to replace the route along Scenic Loop Road. Further north, several sections of the route between Nelson City and Comfort were straightened and a new bridge over the Guadalupe River (today's Business US 87) was built.

San Antonio's first expressway was built to provide a bypass for US 87 from Fredericksburg Rd. at Woodlawn into downtown. US 87 from Woodlawn to Huebner was shifted from Fredericksburg Rd. to I-10 after it was completed in the mid '60s. 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)

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

Fredericksburg at I-10 looking northwest (ca. 1950)
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.

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

Fredericksburg at Donaldson looking southeast (ca. 1959)

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

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

Fredericksburg at Vance Jackson looking southeast (1959)

Fredericksburg at Gardina looking northwest (1959)

Fredericksburg at Gardina looking southeast (1959)

Fredericksburg at Williamsburg looking southeast (1959)

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

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

Fredericksburg Road - Location unknown (1921)

Fredericksburg Road - Location unknown (1921)

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

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

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

Business US 87 and Ave. A in Comfort looking south (ca. 1935)
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.

Click here to return to the historical photo galleries page.

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This page and all its contents are Copyright 2019 by Brian Purcell

The information provided on this website is provided on an "as-is" basis without warranties of any kind either express or implied.  The author and his agents make no warranties or representations of any kind concerning any information contained in this website.  This website is provided only as general information.  The author expressly disclaims all liability with respect to actions taken or not taken based upon the information contained herein or with respect to any errors or omissions in such information.  All opinions expressed are strictly those of the author.  This site is not affiliated in any way with any official agency.