Jamestown was built upon the site of a semi-permanent Cherokee village, which probably made use of the many natural rock shelters in the area.

The last remaining spring is located in the Mark Twain City Park, just northeast of the county courthouse.

The notorious "Tinker Dave" Beaty formed his Union scout company in Fentress County to battle with the pro-Confederate guerrilla's led by Champ Ferguson.

He built the Alvin C. York Agricultural Institute, a high school in Jamestown.

[8] The city is located along the western edge of the Cumberland Plateau near the center of Fentress County.

According to the United States Census Bureau, the city has a total area of 2.9 square miles (7.5 km2), all land.

As of the 2020 United States census, there were 1,935 people, 875 households, and 396 families residing in the city.

In 2010, Jamestown had the sixth-lowest median household income of all places in the United States with a population over 1,000.

The local newspaper serving Jamestown is the Fentress Courier, published each Wednesday in print and on the internet.