1,700 acres (690 ha) of surrounding land was granted to the Virginian William Prince for his service during the American Revolution.

The county court accepted the proposal in July and named the new community Princetown, which shortened to Princeton by the time of the Eddy Grove.

In December 1864, Confederate-allied Kentuckian cavalry under Gen. Hylan B. Lyon raided the town and razed the courthouse, which was serving as a Union garrison.

A large, violent, and historic tornado tracked through the southern part of Princeton during the late evening hours of December 10, 2021.

Interstate 69 runs along the northern edge of Princeton, with access from exits 79 (Kentucky Route 91) and 81 (KY 293).

This eclipse was viewable across the United States, with its maximum peak in Princeton, where totality lasted 2 minutes and 40 seconds.

One of the highlights of the Black Patch Festival each year is the gospel concert held at the Princeton First Baptist Church.

The festival is named after the unique variety of "Black Patch" tobacco grown in the surrounding areas of western Kentucky and northwest Tennessee.

A vigilante force called the Night Riders was formed to combat the Duke monopoly and terrorized those who cooperated with the tobacco company by destroying crops, burning warehouses, and even physical intimidation.

On December 1, 1906, the Night Riders raided Princeton and burned the largest tobacco factories in the world.

With thousands of people, plus a large number of horses, wagons, and other livestock, water was of the utmost importance for survival.

Big Spring Park, a certified site, is owned by the City of Princeton and is accessible to visitors.

Pennington, a nationally recognized musician,[16] continues the tradition of "thumbpicking" popularized by Merle Travis and further developed by instrumentalists such as Chet Atkins.

It is the only restored Art Deco theatre in a small community that shows current movies on three screens.

It was emphasized that with community participation, donated funds and volunteer labor, Princeton's downtown could be transformed.

[18] In 2008 the Kentucky Heritage Council honored the town with the Ida Lee Willis Memorial Foundation's Preservation Award "in recognition of the significant accomplishment involving the preservation and historic restoration through increased awareness and civic involvement" for "Let's Paint the Town!".

[19] The original 400 acres (160 ha) of land were donated by the citizens of Caldwell County, who raised funds by public subscription for the purchase.

With an initial staff of one, early program emphasis was placed on rebuilding the depleted cropland areas and applying conservation practices to the badly eroded steeper land.

Experimental work on liming, fertilizer application, and use of improved seeding mixtures was begun and structures for crop and animal production research were added.

Outstanding livestock herds were established and research with pastures, grain crops, tobacco, fruits, and vegetables was expanded.

It also runs a vocational school that offers programs in carpentry, agriculture, automotive technology and health services.