Jamestown, Kentucky
Looking for the best chillin in Jamestown? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Jamestown. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Jamestown
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Parkers Lake, Kentucky
Hike to Natural Arch in Daniel Boone National Forest
1 mi / 300 ft gainNatural Arch is located in the Daniel Boone National Forest near the border of Tennessee and Kentucky. Once you get inside of the park there are many picnic tables and other areas to eat and sit and paths to walk on. The main attraction of the park however is the 100 foot wide arch that spans ove...Read more -
Jamestown, Tennessee
Natural Bridge Loop
1.05 mi / 148 ft gainThis trail is located in Pickett State Park which is a close neighbor to Big South Fork National Recreation Area. This is one of the many trailheads that connect to the Natural Bridge loop however, this trailhead is the closest to the natural bridge. From the road it is only a few hundred feet wa...Read more -
Jamestown, Tennessee
Hike to Indian Rockhouse
0.4 mi / 65 ft gainThis hike is a great, short hike for all ages. It shows the sandstone formation of the area very well and features a large cliff, an overhang, and a small stream at the bottom. The hike is only 0.4 of a mile total and has a small elevation change. It is probably the easiest hike in this area. Th...Read more -
Jamestown, Tennessee
Hazard Cave Loop
5.01.51 mi / 210 ft gainHazard Cave is a gorgeous very large sandstone formation. The hike is located in Pickett State Park which is right next to Big South Fork National Recreation Area. This hike is the shortest option to get to Hazard Cave. If you are looking for a longer hike you can take the entire loop hike to get...Read more -
Jamestown, Tennessee
Explore Pickett State Fire Tower
This tower was built by the CCC in the 1930s. The tower is easy to climb and safer than most fire towers. The top of the tower is open so you can get a 360 degree view of the surrounding area. The tower is located within the Pickett State Park and is right on the side of the road and has easy acc...Read more -
Jamestown, Tennessee
Stargaze at Astronomy Field
This Dark Sky Park is a part of the Pickett State Park. It was established in 2015. It is one of the only IDA registered dark sky parks in the east. I have been all over the United States stargazing and this is still one of the best spots I have been to. The astronomy field offers a free and easi...Read more -
Jamestown, Tennessee
Twin Arches Loop
1.22 mi / 177 ft gainThe trail starts at the parking lot which has some nice bathrooms and a nice small picnic area that is open year-round. From the trailhead, you will follow the signs that will lead you to a short mostly flat, 7-mile hike to the first arch. Once you get to the first arch there is a small area with...Read more -
Oneida, Tennessee
Backpack to Angel Falls Overlook in the Big South Fork
4.06.4 mi / 800 ft gainStarting at a very small parking space, you head onto a fairly overgrown trail for half a mile. The trail then begins to thin out and is not as overgrown. Keeping a steady incline, you almost instantly feel the burn in your calves. At around 2 miles in, there is a single grave from a baby that l...Read more -
McCreary County, Kentucky
Photograph Cumberland Falls
5.0The Cumberland Falls State Resort Park is home to several waterfalls, with the Cumberland Falls being the largest, most prominent, and most well known. It is also called the Niagara of the South due to its size and volume of water flow. It is famous for being the only place in the Western Hemisph...Read more -
Oneida, Tennessee
Paddle the Big South Fork of the Cumberland River
This is an awesome trip because it allows you get a little taste of what it could have been like to explore the nation by waterway hundreds of years ago. Paddling as a means of traveling is an ancient practice. You are able to glide through nature, more a part of it rather than an unwelcome intru...Read more -
Oneida, Tennessee
Short hike to East Rim Overlook
0.2 mi / 50 ft gainThis trail is located in Big South Fork National Recreation Area. This is more of a walk than a hike. The entire trail is paved except for the wooden boardwalk overlook at the end. The overlook shows the gorgeous views of the river valley and some of the rock formations in the area. The trail is ...Read more -
Jamestown, Tennessee
Northrup Falls
4.21.39 mi / 98 ft gainTruly a hidden gem, this trail seems to get little to no attention, yet is absolutely amazing. To get to the trail from I-40 near Crossville, Tennessee, take Highway 127 north toward Jamestown. Before getting to Jamestown, turn right on State Route 296 east, toward the town of Allardt. In Allardt...Read more