Montgomery was founded in 1837 on a ridge between Town Creek to the north and Stewart Creek to the south, a mile south of the place where Indian trader Andrew Montgomery had opened a general store in 1823. Montgomery's store lay near the crossing of the Lower Coushatta Trace, which ran east–west between the Trinity and Brazos rivers, and the north–south Loma del Toro Trail. In 1837, the Republic of Texas created Montgomery County and designated Montgomery the county seat. Although the streets of Montgomery tend to meet at right angles, the town plan is unusual in being loose, rather than uniformly surveyed.
After Conroe, fifteen miles to the east, was founded in the 1880s along what had become the International and Great Northern Railway line, Montgomery County voters moved the county seat out of Montgomery in 1889, effectively arresting its development. As a result, Montgomery is a remarkably preserved Southern town, all the more surprising given its proximity to Houston's metropolitan sprawl. Master builder John E. Shelton, active in the 1850s, left his architectural mark on Montgomery, as did builder John Bishop in the 1870s and 1880s.
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