Hiking in the summer can be a painful exercise. When the sweat is dripping down your face and the mosquito bites swell to grape-sized welts on your legs, it’s easy to wonder if the trail is worth the tumult.

It’s always worth it after you’re safely back in your car with the AC on. This is how I felt in late June on the Cougar Nature Trails, a system of easy and moderate paths through the woods behind North Warren Central School in Chestertown.

Cougar Nature Trails

I was on a quest to finish the Chester Challenge, and the Cougar Nature Trails were next in line. Despite the bugs and the coming heat wave, I needed that next notch in my hiking belt. With that in mind, I parked in the school parking lot and walked down a grassy hill to the trailhead.


The forest was dark and damp after two full days of pouring rain. The narrow, crowded trail begins with a small wooden foot bridge over a shallow stream. Mosquitos assaulted me as soon as I stepped off the grass and into the woods.

Cougar Nature Trails

Following the trail was easy. Yellow and black arrows point hikers in the exact direction the path takes. A steep hill is the first challenge on the Cougar Hill trail, which is the main loop in this system.

The hill is short and sweet, and another shorter climb follows. At the top of that hill is an open field and the option to take the Cub Trail. I was doing the Adirondack Slap at this point, killing buzzing mosquitos left and right, so I quickly kept moving into the next section of dark forest. A lonely metal bench sat at these crossroads, waiting for someone who needs a rest.

Cougar Nature Trails


I chose to continue on the Cougar Hill Trail. The trail remained easy, with a few short climbs but mostly flat trails. The path is lined with downed trees, making the correct course abundantly clear. Brown signs depicting a cross-country skier mark the suggested winter routes.

Cougar Nature Trails

After another long wooden bridge over a stream, and two more short and simple climbs, you reach a large, obstructed semi-open clearing. This is the summit of Cougar Hill. A small window through the trees reveals lush, green mountains in the distance. A rope and a “Do Not Enter” sign mark the boundary of the clearing.

Cougar Nature Trail


I wanted to stop and relax, sit on a downed log, and take a sip of water. The mosquitos had other things in mind. I left the clearing quickly and started walking down the backside of the Cougar Hill loop.

Cougar Nature Trails

The trail continues in much the same way, moving downhill or maintaining a level path. Much of the trail is on the side of a sloping ridge. Before long, I had completed the loop and was close to the parking lot.


The Cougar Nature Trails are great for a quick and easy sprint through the woods. The view from the top leaves something to be desired, but the trails are clean and beautiful, and the time and energy investment is low. I look forward to hitting these trails with my snowshoes when the snow starts to fall.