Overlook Mountain

Situated within the Catskill Forest Preserve, Overlook Mountain rises 3,140’ feet above the town of Woodstock. I live on its western slope, just about a mile from the trailhead where the 2 1/2 mile ascent begins, passing the ruins of the old mountain house before reaching the fire tower and summit, with its breathtaking views of the Hudson Valley and Central Catskills.

At the top, the landscape transforms—sometimes bathed in morning clarity, sometimes swallowed by fog, wind, and ice. These walks, though rhythmic and familiar, are never the same. The mountain is a place of contrast—stillness and movement, solitude and change.

For the past 30 years, I’ve climbed this mountain at first light, often alone, moving through its seasons and quiet offerings. Beneath the simple act of walking—of moving through this landscape—is something deeper: a search for meaning, a connection to the land and its wildness. I see it in the ferns and mushrooms, the massive rocks, the cold spring water emerging directly from the mountain. I feel it on the flat boulder halfway up, where I lie back, breathing in the cool, clean air, resting before the final stretch to the top.