San Augustine is at the junction of U.S. Highway 96, State highways 21 and 147, and Farm Roads 711, 353, 3230, 2213, and 1277, on the Atchison, Topeka and Santa Fe Railway, thirty-two miles east of Nacogdoches in north central San Augustine County. Ayish Bayou flows through the town two miles west of the public square, and Carrizo Creek has been dammed just southwest of San Augustine to form City Lake, the source of municipal water. The original inhabitants of the area were the Ais (Aies, Ayish) tribe of the Hasinai Indians. The first European visitors were probably part of the Moscoso expedition early in the 1540s. The Indians remained undisturbed for almost 150 years, until French traders from Natchitoches ventured into the vicinity, discovering their village near the site of present San Augustine. The Spaniards returned in 1691, when Domingo Terán de los Ríos traveled through the area, cutting a path later called the Old San Antonio Road. In 1717 Father Antonio Márgil de Jesús established Nuestra Señora de los Dolores de los Ais Mission near the Ais village on Ayish Bayou. After being abandoned because of the threat of a French invasion in 1719, the mission was reestablished on the site of modern San Augustine by the Marqués de San Miguel de Aguayo in 1721. But permanent settlement did not occur until after 1779, when the French threat became less ominous. Then Anglos and scattered remnants of the Kickapoo, Cherokee, Delaware, and Shawnee Indians immigrated from the southern states, particularly Mississippi, Alabama, Georgia, and Tennessee. Among these pioneers, who called the area the Ayish Bayou District, were John Quinalty, Susanna Horton, Martha Lewes, Edmund Quirk, and Chichester Chaplin. Antonio Leal and his wife, Gertrudis de los Santos, settled at the site of San Augustine and built a small house with corrals to accommodate wild mustangs gathered by Leal and Philip Nolan for sale in Louisiana. In 1800 Leal sold the property to Pedro Buigas, who sold it the following year to Edmund Quirk.
In 1827 Ayish Bayou residents elected municipal authorities, even though the Mexican government had not officially recognized the district. Nathan Davis became the first alcalde for Ayish Bayou District, George English the first sheriff. When the Fredonian Rebellion began in 1827, most people along the bayou abandoned their homes because advancing Mexican and rebel forces threatened their safety. Despite this apparent unwillingness to take sides, these settlers soon became involved in protests against the Mexican government. In 1832 they participated in the battle of Nacogdoches, and they sent representatives to the Convention of 1832. Sam Houston was one of their delegates to the Convention of 1833. In 1832, under the leadership of alcalde William McFarland, residents decided to construct a permanent settlement in a central location. A committee of fifteen men chose the banks of the Ayish Bayou, which had been the heart of local activities since Indian occupation, and purchased the land in January 1833 from Edmund Quirk for ninety dollars. Thomas S. McFarland was appointed to survey their purchase and plat 356 lots on forty-eight city blocks in a grid pattern, perhaps the first time that such a method was used in Texas. The streets were forty feet wide, and squares were reserved for the school, churches, municipal buildings, a market, and the jail. The following year, under alcalde Charles S. Taylor, the municipality of San Augustine was established by Mexican law. Mexican officials supposedly chose the name to honor St. Augustine of Hippo. Because the population of the district was more than 2,500, inhabitants could officially elect two councilmen, a clerk, a chief justice, a primary judge, and an alcalde.
In the 1830s San Augustinians took an active part in the Texas Revolution. Early in 1836 Houston was elected commander of the Texian forces at San Augustine-and then for all of Texas. In April the town was again abandoned during the Runaway Scrape, but citizens returned to their homes after the victory at San Jacinto. Under the Republic of Texas, San Augustine, the only sizable town in the county, became the county seat. In 1837 settlers elected a chief justice, a sheriff, a county clerk, a district clerk, a surveyor, and a coroner. On June 5, 1837, the town was incorporated. But the end of the war failed to bring peace. In 1838 local resident and war hero Henry W. Augustine led a force against Mexican insurgents in the Córdova Rebellion. In July 1839 Texas troops drove the Cherokee and allied Indians out of East Texas (see CHEROKEE WAR). Settlers were also affected by the Regulator-Moderator War. But even in such turmoil, the little village continued to grow. Without the restraint of Mexican law, Protestant organizations and congregations were formed. In 1836 the San Augustine Bible Society managed to collect more than $172. In 1838 Littleton Fowler established the First United Methodist Church. The first Presbyterian congregation in Texas, with twenty-four members including two slaves, was founded by Hugh Wilson in 1838 when he began preaching at nearby Goodlaw School. That same year Jerusalem Memorial Colored (later Christian) Methodist Episcopal Church was built on a town lot belonging to George W. Teel. I. D. Thomas had constructed the first store in town, and a saloon, hotels, and other businesses soon developed. McFarland Lodge, the third official Masonic organization in Texas, was founded in 1837 under the leadership of William McFarland and was joined soon by Red Land Lodge No. 3 and Rising Star Chapter No. 4. That year W. W. Parker also began publishing the San Augustine Red-Lander. Mrs. Stewart's Female Academy was only one of several private schools in the area. Local architects Augustus Phelps and Sidney A. Sweet designed and built several impressive Greek Revival homes. Mail was delivered by Josiah F. Palmer, who had several delivery contracts. The short-lived University of San Augustine was incorporated on June 5, 1837, the same day as the town. The school finally opened in 1842 only to close five years later without issuing a single degree. Wesleyan College, chartered by an act of Congress early in 1844, was only slightly more effective. A Methodist school, under the direction of Rev. Marcus A. Montrose, granted only two degrees before closing in 1847. The University of Eastern Texas, incorporated on March 8, 1848, received the property and endowment of the University of San Augustine, and its board of trustees united with the trustees of Wesleyan College. This school closed, however, after only a few years. The first post office, originally called Kendricks, opened in March 1847, but the postmaster changed the name to Ayish Bayou the following September. In March 1848 the postal facility was officially named San Augustine. Two years later Reverend Henry Samson formed the Christ Episcopal Church congregation at the invitation of Frances Cox Henderson. Throughout the republic era the customhouse at San Augustine collected duties on imports from the United States totaling $62,105.90.
The customs office had also served as the municipal building, but in 1854 a new two-story brick courthouse became the center of town activities. Eight new mercantile establishments and one drugstore had opened, and Red Land Lodge No. 3 had founded the Masonic Institute to educate local children. By 1860 San Augustine was a shipping center for cotton, but the Civil War interrupted this lucrative business. In the summer of 1861 San Augustine sent three companies into battle, and these were later followed by others. In 1862 a battalion of the Third Texas Brigade was stationed in the town to protect against invasion. Throughout the 1870s businesses struggled to recuperate but never recaptured the success of the antebellum years. In 1884 there were 600 residents. Local businesses included cotton gins, a gristmill, and two small sawmills, but the large enterprises that had once accommodated travelers remained closed. One school was in operation, and two newspapers, the Herald and the Saxon, were still in publication. In 1890 a fire destroyed a large part of the town, but rebuilding began soon after. The old courthouse was torn down and replaced with a new one. The gristmill and cotton gins were still functioning, and seven general stores had opened. Other enterprises included two saloons and three law offices. East Texas Progress and the News had replaced the Herald and the Saxon. The town's 700 residents could attend any of five churches, including Methodist, Episcopal, and Presbyterian. The number of general stores had grown to eleven, and the postmaster reported "good schools," a hotel, a flour mill, and a cotton gin. In 1901 the Gulf, Beaumont and Great Northern Railway extended its tracks to San Augustine. The Santa Fe Railway system acquired the line in 1903 in order to transport lumber and other goods to and from the area, providing railroad jobs and making large sawmill operations feasible for the first time. By 1910 San Augustine was a town of 1,200. In 1914 residents numbered 1,300. The two weekly papers were the Tribune and the Cotton Belt News. Gristmills and cotton gins still operated, and two blacksmiths had opened shops. There was even a local telephone exchange, and R. N. Stripling ran a large pharmacy. Stores grew larger, as more farmers sold their truck crops, dairy products, fruit, and eggs in town. Residents were served by the First National Bank. In 1927 the old courthouse was demolished and replaced with a two-story stone structure. At that time citizens had access to city-owned water, light, and sewage utilities, as well as an ice plant and natural gas services. Children attended new schools, including a one-story high school.
The growth and development of the 1910s and 1920s was, however, followed by the Great Depression. Lumber companies, having exhausted the best of the East Texas timberlands, moved out, thus eliminating an important source of income. Twenty-seven businesses closed, workers lost their jobs, and farmers had no market for their produce. Aid came in the form of such federally funded programs as the Work Projects Administration and the Civilian Conservation Corps, as well as governmental loans. While some sawmills eventually reopened, they could not operate at previous levels of output. By the beginning of World War II the Deep East Texas Electric Cooperative, which provided electricity for four counties, was headquartered in San Augustine. The town also had eighty businesses, including a car dealership, and many were located around the town square. By 1960 the population had increased to 2,584 and the number of businesses to 130. These enterprises included an additional car dealership, a locker plant, two banks, and three pharmacies. Citizens could attend any of ten churches or belong to such organizations as the San Augustine County Historical Society, the Daughters of the Republic of Texas, or the San Augustine County Trail Riders Association. Among the recreational facilities was the Fairway Farm Country Club, an eighteen hole, 300-acre golf course designated as one of the 200 toughest in nation. The town also included two dental and three doctor offices, a law firm, and two funeral homes. The Tribune and a new paper, the Rambler, were in publication-both as weeklies. This development continued through the 1970s and 1980s. San Augustine remained the largest city in the county. A public library containing 15,000 volumes opened, a new jail was constructed, and a loop was built to direct traffic around the town. Publication of the Rambler was discontinued, but only after the press had published several volumes dealing with local and Texas history. The spring crafts fair and the annual Tour of Medallion Homes and Historic Places have become popular tourist attractions. Homes bearing historic medallions include those of Stephen W. Blount, Matthew Cartwright, George L. Crocket, Ezekiel W. Cullen, Almanzon Huston, and Philip A. Sublett. By 1992 the population totaled 2,337. In 2000 the population was 2,475.