Overlook Mountain Trail
A 4.6-mile round trip hike up an old road to a fire tower with views over the Hudson Valley, the Catskills, and on clear days all the way to the Berkshires. Along the way, kids pass the ruins of the Overlook Mountain House hotel, a crumbling stone building that feels like discovering a castle in the woods. The fire tower at the summit is restored and climbable. The trail is wide and straightforward but climbs steadily. This hike combines history, mystery, and mountain views in a way kids love.