Plan with
Confidence
Path Type
Loop
This route begins at the Gardner Hollow Road trailhead in West Mountain State Forest. From the trailhead, follow Penny Road Trail north through mixed hardwood forest, staying on the main path as it gradually gains elevation. At the first major junction, continue north onto Ridge Trail North. This section climbs more steadily along a wooded ridgeline, offering occasional filtered views to the east. Stay on Ridge Trail North until reaching the Connector Trail, then turn right (east) to cross over to East-West Trail.
After a short stretch east on East-West Trail, turn right again onto Pond Trail heading south. This quieter section descends gently toward Blackberry Pond, with opportunities for wildlife viewing and a shaded rest near the shoreline. After reaching the pond, retrace your steps north briefly along Pond Trail, then continue north on the Red Trail. At the next signed junction, turn left onto Blue Trail, which winds south and reconnects with Ridge Trail North. Retrace the original approach back to Penny Road Trail and return to the Gardner Hollow Road trailhead.
This route combines varied terrain, multiple trail segments, and a remote forest pond for a rewarding moderate day hike in the Hudson Highlands.
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