Thompson Pond and Stissing Fire Tower Loop

This route begins at the trailhead near Lake Road in Pine Plains and forms a full circuit around the flanks of Stissing Mountain. From the start, the trail heads south towards through low forest and crosses gentle terrain along Thompson Pond before climbing steadily into steeper, rockier ground. At a signed junction partway up, turn left to stay on the main ascent route. The climb becomes more rugged before reaching the ridge, where a spur leads to the summit fire tower. The tower offers expansive views across the Hudson Valley, including the Catskills to the west and Connecticut hills to the east. After enjoying the summit area, head north and continue along the ridgeline. The route descends gradually through mixed hardwood forest, with bursts of fall color in autumn and frequent bird activity in spring and summer. Several seasonal stream crossings occur lower on the descent, but there are no reliable water sources higher up. Ticks are common in warmer months, and the trail may be muddy after rainfall. The route completes its loop by reconnecting with the initial approach and returning to the Lake Road trailhead. Clear views, a classic fire tower, and varied forest make this one of the best moderate day hikes in the Hudson Valley.