Jamestown is the gateway to the Big South Fork Recreation Area
The Big South Fork of the Cumberland River cuts a gorge through the Cumberland Plateau, creating the Big South Fork National River & Recreation Area, a 200-square-mile park that stretches across Tennessee and Kentucky. Jamestown serves as a gateway to the area for many of the 500,000-plus people who visit every year. “It’s small-town living next to Big South Fork,” says Todd Stephens, a Realtor with Crye-Leike Brown Executive Realty who was born and raised in Jamestown. “Equestrian properties are real big. A lot of these communities butt up against the park, and then people can ride directly into the park on the horse trails.”
Hiking, horseback riding and camping at Big South Fork
About 20 miles from town, the Bandy Creek Visitor’s Center of Big South Fork has a campground, a pool and miles of trails. Plenty of visitors from across the region venture into the park, but Jamestown locals have much easier access. Some residents can even hike or ride their horses right into the park. In town, Jamestown Community Park is the main spot for recreation, including several playgrounds, a basketball court and a baseball field. Plus, Jamestown City Pool is next door at the community center.
Ranch-style homes near downtown, and larger lots on the outskirts
Just south of the town center, houses sit along narrow streets shaded by tall trees. Ranch-style builds from the 20th century are most common, and manufactured homes are also scattered across the community. These homes often sell for $30,000 to $200,000 based on size and condition. Farther from the town core, lots get larger. Farmhouses can sit on as much as 25 acres, and many have space for horses. These tend to sell from $200,000 to $525,000. Stephens says land is also a hot commodity in the area, and some buyers build their own homes.
Education at Fentress County schools or the York Institute
The Fentress County School District serves Jamestown and receives a B-minus overall grade from Niche. Most students in the community start at either Pine Haven Elementary, which gets a B-minus grade, or C-plus-rated York Elementary. Both schools teach kindergarten through eighth grade. B-minus-rated Clarkrange High is the district’s only high school. The school partners with Roane State Community College for a dual studies program, offering students the chance to earn college credit while completing their high school degree. Jamestown is also home to the York Agricultural Institute, which receives a B-plus. “It’s one of the largest on-campus high schools in the United States,” Stephens says of the 400-plus-acre campus. “It’s the only state-run high school in Tennessee.”
Shopping and dining on Main Street, or more options in Cookeville
Several businesses sit near the Fentress County Courthouse at the center of town. Campfire Coffee serves hot drinks, bagels and sandwiches, while locally owned shops include the Time After Time clothing store. Outside downtown, Main Street has fast food restaurants like McDonald’s and shopping centers with community staples like Garcia’s Mexican Restaurant. Walmart is just off Central Avenue and has groceries and other essentials, while Penny’s Produce has sold locally-grown produce in Jamestown for over 70 years. For more shopping, residents head to Cookeville, 50 miles away.
The annual county fair, plus music festivals at Catoosa
As the county seat, Jamestown hosts the Fentress County Agricultural Fair each August. The event features the traditional animal and produce shows and is capped off with a demolition derby. Just outside the community, the Catoosa Event Center hosts concerts and festivals. The area hosts annual events like the Catoosa Music and Adventure Festival, and attendees can camp alongside a lake and a natural bridge.
Roughly 45 miles from Crossville via Highway 127
Jamestown is roughly 45 miles from Crossville, one of the larger cities in the area. The state is working to improve the highway between the two areas. Some projects, including a new bridge over Clear Creek just south of Jamestown, will wrap up in 2026, with disruptions along the route until completion. The Kentucky border is 20 miles north on Highway 127. The University of Tennessee Medical Center has an emergency room in Jamestown. McGhee Tyson Airport, near Knoxville, is about 80 miles away and has the closest commercial flights.
