Gilead Rupe, founder of Lexington, established a ferry on the Missouri River in 1822. In 1823 Lexington became the county of seat of Lafayette County and grew quickly. By the 1830s and 1840s Lexington became a bustling and prosperous merchant hub and during this time became the largest city west of St. Louis.
The Aull brothers established the first mercantile store in 1822 and the business soon grew into a chain of stores in the area that also established stores in Independence, Liberty, and Westport. The Aull brothers soon had competition as many other merchants began setting up shop in the growing city. They were soon joined by planters and farmers who specialized in growing, hemp, tobacco, and raising cattle. Working the hemp and tobacco fields required enslaved labor, which led to the county to have one of the largest enslaved populations in the state.
Because of Lexington's popularity as a trading hub in the mid-19th century, it became a mecca for trappers, settlers, and emigrants making their way west. The Santa Fe, Oregon, California, and Mormon trails all began in this part of western Missouri, and because of Lexington's trading background, many merchants and outfitters had established their shops to service these travelers. Rope walks, slaughter houses, a foundry and a furniture factory were among the early Lexington industries. In the 1840s Russell, Majors and Waddell, the largest trading firm in the West, established their headquarters on Lexington's Main Street. In the 1850s these three men had 3500 wagons carrying goods from Missouri to Sacramento, Denver, and other points of interest in the western frontier.
The success of Lexington's trading industry led to the growth of the town's steamboat trade, which would in turn become a profitable enterprise. Productive coal mines, among the first in the state, were also dug into the river bluffs surrounding Lexington to provide fuel for the river steamers that came through the town. Merchants, farmers, planters and other businesses throughout Missouri and the frontier sent their goods to Lexington to be sold and distributed via the major waterway of the Missouri River. The wharf at Lexington, situated along the Missouri River, became the center of commerce for the town. In 1852 one of the worst steamboat accidents in Missouri history occurred along the Lexington portion of the Missouri River. The boilers on the side-wheeler steamboat Saluda exploded, killing over 150 people. Some of the dead included Mormon passengers who were making their way to Salt Lake City.
By the time of the American Civil War, Lexington was a bustling and important city along the Missouri River in western Missouri. Because of the this, the United States Government wanted to control this strategic location and sent troops to occupy and hold the town. This led to two of the larger battles in the Trans-Mississippi theater of the conflict occurring in and around the city.
The first and more well known battle of Lexington is sometimes referred to as the Battle of the Hemp Bales. On September 12, 1861, about 15,000 soldiers of the Missouri State Guard, led by Major General Sterling Price, besieged a Federal garrison of 3,500 troops in the Masonic College commanded by Colonel James A. Mulligan. On September 18, General Price's army mounted an assault, with some of Price's army using hemp bales as moving breastworks while they moved up the river bluffs and closed in on Mulligan's headquarters. On September 20, 1861, Mulligan's troops surrendered to the larger Confederate force, ending the first battle for control of the city.
The Second Battle of Lexington was a part of Price's Missouri campaign in the fall of 1864. The fighting took place on October 19, 1864, with a Union army of 2,000 men making a stand against a larger Confederate force of 8,500 men. This battle also resulted in a Confederate win, but was overshadowed by the larger and more important engagements that occurred to the west in Independence and Westport, where General Price was eventually defeated.
Lexington also saw much guerrilla activity during the Civil War. Two months after the Civil War ended, many of these guerrilla fighters decided to take advantage of the special Federal amnesty that was declared for guerilla forces who had refused to honor the cease fire. They decided to turn themselves in at Lexington, but while riding into town, reportedly under a white flag, Union soldiers from the 2nd Wisconsin Cavalry fired upon the group. Jesse James, who was reportedly among this group, was shot in his right lung. Because of this incident, the James Younger gang uncoincidentally targeted the Alexander Mitchell bank in Lexington for the second daylight bank robbery in United States history. In December 1866, Archie Clement, an accomplice of the James brothers and perhaps one of the most notorious of all of the guerrilla fighters, terrorized the town and was shot from his horse and killed by a sniper perched in the second floor of the Courthouse.
Lexington never returned to its pre-war prominence, having been replaced by Kansas City as the most important city in western Missouri. Particularly harmful to the growth of the town was the arrival of the transcontinental railroad, which helped to supplant the river commerce, which had proved so important to the town's identity and commerce. Responding to this change, the city established a number of institutions of higher education, leading the town to identify itself as the "Athens of the West." Especially significant were three schools for women, including the Elizabeth Aull Seminary, Lexington Ladies' College, and Central College for Women. The Wentworth Military Academy, which was founded in 1880, also helped draw students to Lexington, not only from the United States, but from around the world, until it closed in 2017.
Visitors to the town can enjoy spending time at the Battle of Lexington State Historic Site, which commemorates the Civil War battles that occurred in Lexington. Visitors can also learn more about the community's history by visiting the Lexington Historical Society. Those interested in learning more about the history of the Wentworth Military Academy can also visit the museum devoted to the school.