It is the home of the Battle of Lexington State Historic Site, and of the former Wentworth Military Academy and College, which operated from 1880 to 2017.

It was platted in 1822[10] near William Jack's Ferry, which had been established three years earlier on the south bank of the river.

The Aull Brothers firm soon had a frontier chain, also operating stores in Independence, Westport and Liberty.

With the emphasis on trade and agriculture, Lexington and Lafayette County also had one of the largest slave populations in the state.

Rope walks, slaughter houses, a foundry and a furniture factory were among other early Lexington industries.

In the 1840s, Russell, Majors and Waddell, the largest trading firm in the West, established its headquarters on Main Street.

In the 1850s, these three men had 3500 wagons carrying goods from Missouri to Sacramento, Denver, and other points, and in 1860, they would found the Pony Express.

The steamboat trade on the river became a hugely profitable investment, and the wharf was a center of commerce.

The side-wheeler Saluda was carrying 250 Mormons en route to Salt Lake City when its boilers exploded, killing over 150 people.

[citation needed] In March 1856, the Arabia steamboat was stopped and searched by pro-slavery Border Ruffians near Lexington, who confiscated 100 rifles and 2 cannons en route to the slavery-free Kansas Territory from the abolitionist Massachusetts Aid Society.

On September 12, 1861, between 6,000 and 10,000 soldiers of the Missouri State Guard, led by Major General Sterling Price, began a siege against the Federal military post in the old Masonic College commanded by Colonel James A. Mulligan.

The battlefield on the bluffs of the Missouri River is now a state park, and the cannonball stuck in one of the upper pillars of the Courthouse has become a symbol for the town.

Two months after the Civil War ended, many of these guerrilla fighters who had refused to honor the cease fire finally decided to take advantage of the special Federal amnesty that was declared for such forces and turn themselves in at Lexington.

While riding into town, reportedly under a white flag, they were fired upon by Union soldiers from the 2nd Wisconsin Cavalry, and Jesse James was severely wounded in the right lung.

Some credit this event as a major contributing factor to his post-war career as a legendary bank robber.

In December 1866, Archie Clement, an accomplice of the James brothers and perhaps the most notorious of all 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.

Several institutions of higher education were established, leading the town to bill itself as the "Athens of the West".

Dunbrooke began as a dress shirt company in 1939 in Lexington and became a nationwide logoed apparel manufacturer.