[6] The area of present-day Hopkinsville was initially claimed in 1796 by Bartholomew Wood as part of a 1,200-acre (5 km2) grant for his service in the American Revolution.

[7] Following the creation of Christian County the same year, the Woods donated 5 acres (20,000 m2) of land and a half interest in their Old Rock Spring to form its seat of government in 1797.

By 1798, a log courthouse, jail, and "stray pen" had been built; the next year, John Campbell and Samuel Means laid out the streets for "Christian Court House".

Confederate support in Hopkinsville and Christian County was evident in the formation of the "Oak Grove Rangers" and the 28th Kentucky Cavalry.

After Confederate forces retreated to Tennessee, however, Camp Joe Anderson was established by the Union to the northwest of Hopkinsville in 1862.

Gen. James S. Jackson had been a Hopkinsville attorney before the war and was killed in service to the Union at the Battle of Perryville in October 1862.

[citation needed] The occupation of Hopkinsville changed at least half a dozen times between the Confederate and Union forces.

In December 1864, Confederate troops under Gen. Hylan B. Lyon captured the town and burned down the Christian County courthouse which was being used at that time by the Union army as a barracks.

Another skirmish between Union and Confederate forces took place in the field opposite Western State Hospital near the end of the war.

With societal pressure seeming to fail, the Silent Brigade (probably under Dr. David A. Amoss) organized the Night Riders (not to be confused with the Ku Klux Klan) to terrorize farmers into submission.

[citation needed] On December 7, 1907, 250 masked Night Riders seized Hopkinsville's police station and cut off all outside contact.

On January 1, 2022, an EF2 tornado struck Hopkinsville, removing the canopy from a gas station, and destroying the petrol pumps.

[citation needed] The 2020 census estimated the population of Hopkinsville was 30,683 with a median household income of $39,743 and 23% of people living in poverty.

Ebonite had a broad market share as they own several well-known brand names including Hammer, Dyno-Thane, Columbia 300, Track, and Robby's.

[citation needed] Statistics released in December 2007, by the Kentucky Department of Agriculture, show Christian County continues to be a leading crop producer.

Because of this progressive attitude, Christian County continues to be an agricultural leader and example of good farming practices.

Congressional funding approved for an extension of the Pennyrile Parkway (now I-169) to Interstate 24 in southern Christian County near Fort Campbell.

[citation needed] All commercial air traffic for residents and visitors to Hopkinsville use Nashville International Airport.

[citation needed] Railroad construction and operation in the late 1860s opened markets for agricultural and industrial products.

In 1903, the western division of the Tennessee Central Railway entered Christian County at Edgoten (Edge-of-Tennessee), connecting Clarksville and Hopkinsville.

The Hoptown Chronicle is a "nonprofit, online news outlet that provides public service journalism from the heart of Hopkinsville.

Programming includes the Live at the Alhambra series, public school performances, the Missoula Children's Theatre, and local art exhibits.

[38] From the 1930s to the 1960s, Hopkinsville had two stops on the Chitlin' Circuit tour route, The Skylark and The Chesterfield, which featured Black musical performers like Tina Turner, Count Bassie, Chubby Checker, James Brown, Little Richard, and Cab Calloway.

There is a museum and a burial ground, including two important Cherokee leaders who died during the removal – Fly Smith and Whitepath, along with several large osage orange trees in it and dream catchers hanging from the wrought iron fence.

The Pennyroyal Area Museum, located in the old post office building downtown, has exhibits on the history of Hopkinsville and the Pennyrile region.

The Pennyroyal Area Museum is owned and funded by the city of Hopkinsville and was established to perpetuate the heritage of southwestern Kentucky's rich history.

Area citizens have contributed important roles in the Kentucky tradition from the post revolution era to the present.

Exhibits include the night riders of the Black Patch Tobacco Wars; Edgar Cayce, famed local clairvoyant; Jefferson Davis; period room settings; a pioneer bedroom; a miniature circus; antique quilts; black history; historic modes of transportation; as well as historical license plates from Kentucky.

[citation needed] Every May, Hopkinsville hosts Little River Days, a two-day family fun festival featuring road running, canoe racing, a bicycle tour, arts and crafts, food vendors and live entertainment.

The opening text of the horror-comedy film Attack of the Killer Tomatoes notes that Hopkinsville was invaded by millions of black birds in 1975.