After 1880, Frederick Allardt and Bruno Gernt brought a group of Germans from Michigan to settle in the area. The town was incorporated in 1964.

The city has a total area of 3.8 square miles, all of it land. The city is situated atop the western Cumberland Plateau in a relatively broad area surrounded by rugged hills. Tennessee State Route 52 passes roughly west-to-east through the city, connecting it with Jamestown to the northwest and Rugby to the east. State Route 296 intersects State Route 52 near the center of Allardt, and continues directly westward to U.S. Route 127.

Colditz Cove State Natural Area, best known for the 60-foot Northrup Falls, lies just southeast of Allardt. The Big South Fork National River and Recreation Area lies several miles to the northeast.

Every October the town hosts the Great Pumpkin Festival and Weigh-Off, which coincides with world-wide pumpkin weigh-off.

The City of Jamestown was established in 1823 as a county seat for Fentress County. Jamestown was incorporated as a city in 1837. Both Fentress County and the City of Jamestown are named for prominent local politician James Fentress (1763–1843), who made the appeal for the new county to be carved out of Overton and Morgan counties.

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. Before the founding of Jamestown, the area was known as “Sand Springs” for the many bubbling springs located within the city. The last remaining spring is located in the Mark Twain City Park, just northeast of the county courthouse. This spring provided water to the family of John M. Clemens, father of Samuel L. Clemens (Mark Twain), before they moved to Missouri. John Clemens served as the first circuit court clerk. He also drew the plans for the first courthouse and jail.

During the American Civil War, Fentress County provided four companies for the Confederate Army and three for the Union Army. 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. Neither of these companies were ever mustered into the armies they supported.

World War 1 hero Sgt. Alvin. C. York was born, raised, and died in Fentress County. He built the Alvin C. York Agricultural Institute, a high school in Jamestown. It is one of four state-funded schools in Tennessee.

Jamestown is the headquarters for the World’s Longest Yardsale, also known as the 127 Corridor Sale.

Clarkrange is concentrated around the intersection of U.S. Route 127 and Tennessee State Route 62, in Tennessee’s western Cumberland Plateau region. 

Clarkrange is also the site of Clarkrange High School, the only public high school operated by the county school district.

Clarkrange is named for Cyrus Clark, who operated an inn and cattle ranch in the community during the late 19th century. Prior to Clark’s arrival, the land had been used by local farmers as a free range area for cattle.

Clarkrange High School has claimed 8 state championship titles in Tennessee Class A Girls’ Basketball. The Clarkrange Lady Buffaloes won the title in 1983, 1984, 1985, 1990, 1991, 1995, 2004, and 2009.

Grimsley is an unincorporated community located in the southwestern portion of Fentress County. Grimsley is the fastest growing community located in Fentress County.
Armathwaite is an unincorporated community in Fentress County. It is located along Tennessee State Route 52 between Allardt and Rugby, in Tennessee’s Cumberland Plateau region. The Big South Fork National River and Recreation Area is located to the northeast.

The community was first settled in the 1840’s.  Around 1881, Alwyn Maude, a Rugby colonist, established a post office in the community, and named it for his home village of Armathwaite in England. Oil drilling and logging activities took place in the area during the late 19th and early 20th centuries.

Banner Springs is located in the southern part of Fentress County near the Morgan County line. The first settlers to the area brought seeds and farm animals to include cattle and horses which were used to pull their wagons. In the 1880’s, lumbermen began making railroad ties. Soon stave mills began working the timber. George Carson brought the first sawmill into the community. This led to a timber industry which greatly improved standards of living in the area. By 1940, general agriculture was the primary economic force in the community.
There are two versions of how the community of Boatland, one of the oldest in Fentress County, got its name. One is that flat boats came up the Obed River to pick up tar, turpentine, and other products of the area to take to Nashville and other markets on the river waterways. The other version is that the boats were constructed by the area workmen and then loaded and floated down the river when the rains raised the river to a certain level called a “tide”.
Forbus is an unincorporated community located on U.S. Route 127 in Fentress County. Considered a crossroads community, it is listed on the National Register of Historic Places as an historic distric called the Forbus Historic District. In 1991 it consisted of a general store, one house, and some outbuildings.

Early names for the community were Blue Rock and Gatewood. In the mid-19th century, the community was briefly home to a school known as the Van Buren Institute. Coal was mined in the area as early as the 19th century. In the early decades of the 20th century, the local economy was based on lumbering, barite ,mining, and farming. In the 1930s, the community supported a grade school with 84 pupils and 3 teachers, a high school, a weekly newspaper, and two churches.

The Forbus General Store was built by W. M. Johnson in 1892, and was operated by Johnson until his death in 1941. At one time, the store included a gas-powered gristmill, a blacksmith shop, and several granaries, but only the store stands today. The store purchased produce and furs from local residents, and at one point had a contract to supply locally-grown apples to a Pennsylvania brandy maker. The store in turn sold hardware, clothing, fertilizer and feed, school textbooks, guns, furniture, and caskets. The store’s top floor was once used as a meeting place for an Independent Order of Odd Fellows lodge. The Forbus post office operated out of the store until 1965, and consolidated with the Pall Mall post office in 1972.

The community of Little Crab, about 10 miles west of Jamestown, was one of the earliest sections in the Upper Cumberland region to be settled. When the first pioneers came to it about 1819, it was still a part of Overton County, TN. There are two creeks in the valley – Big Crab, usually called just Crab Creek, and Little Crab. The community took its name from the latter. Little Crab is surrounded on three sides by mountains; on the western boundary is the East Fork of Obey River. East Fork and Crab Creek, which flowed into it, were the main transportation paths for early settlers. For the first century of the community, residents were isolated by a lack of consistently passable roads out over the mountains. The earliest settlers of Little Crab traced their heritage to Virginia, North Carolina, Pennsylvania, Kentucky and a few other eastern or northern states. Most of them, however, were born in Tennessee. They were descendants of the English, the Scots and the Irish, with some Cherokee Indian blood mixed in.

In 1907, the Little Crab School was constructed. The school was also used for meetings for the Order of the Odd Fellows and their auxiliary, the Rebecca’s, who were very active in the community at the time the building was built.

Pall Mall is a small community in the Wolf River valley of Fentress County. Pall Mall is located near the Kentucky-Tennessee state-line in northeastern-central Tennessee.

The World War I hero Alvin C. York was raised in Pall Mall. Sergeant York, was one of the most decorated soldiers of the United States Army in World War I. He received the Medal of Honor for leading an attack on a German machine gun nest, taking 35 machine guns, killing at least 28 German soldiers, and capturing 132 others. This action occurred during the United States-led portion of the broader Meuse-Argonne Offensive in France to breach the Hindenburg line and make the opposing German forces surrender. York is commemorated at the Sgt. Alvin C. York State Historic Park in Pall Mall, which includes the family farmhouse and grist mill. York was laid to rest at Wolf River Cemetery in Pall Mall.

The Shirley community is located in the eastern part of Fentress County and is a rural farming area.
Wilder is an unincorporated community in Fentress County. The town is in the Cumberland Mountains. It reached a population of more than 20,000 as a mining town in the 1920s, but had declined to an estimated population of 249 by 2013