Michael Ciaiola Loop

The Michael Ciaiola Conservation Area Trail begins from a small pullout near 492 Haviland Hollow Road and forms a wooded route through gently rolling hills. Managed by the Putnam County Land Trust, the trail system includes several interconnecting paths that allow hikers and trail runners to adjust route length and difficulty. From the trailhead, hikers enter a mixed hardwood forest that offers shaded walking and a quiet atmosphere just minutes from town. Shortly into the hike, follow trail markers to stay on the main loop, bearing left at the first Y-intersection to explore more remote terrain. The route gains elevation gradually, with occasional rocky footing typical of moderate hikes in the Hudson Highlands. Along the way, seasonal streams and a small pond offer water features, though none are reliably potable—bring treatment if needed. Wildflowers bloom in spring, and birdwatching is excellent year-round. Some sections may become muddy or icy in winter, and ticks are common in warmer months. Dogs are allowed on leash, but camping and fires are not permitted. The trail eventually circles back to the starting point, offering a peaceful day hike option for those looking to explore quiet backcountry trails in southeastern New York.