Cougar Hill

Cougar Hill, also known as the Cougar Nature Trails, begins behind the North Warren Central School in Chestertown, where hikers can park near the tennis courts outside of school hours. This locally maintained trail system offers a variety of route options through mixed hardwood forest, open fields, and gentle ridgelines. The short route climbs steeply to the summit of Cougar Hill, while the longer route follows a more gradual grade through wooded terrain. At a Y-intersection shortly after the trailhead, hikers can choose the shorter Cub Trail or continue on the Eagle Trail for a longer loop through the forest. Interpretive signs along the Cub Trail highlight local flora and fauna, making it a good option for beginner hikers or families with children. Both trails converge near the high point of Cougar Hill, where a small clearing provides a peaceful spot to rest or picnic before heading back. Cougar Hill is part of the Chester Challenge hiking series, offering year-round access for hikers and cross-country skiers.