Greylock in the Round

The Greylock in the Round route begins from the Hopper Road trailhead and follows the Money Brook Trail east, then north, gradually climbing through a wooded valley along Money Brook. After a steady ascent, connect with the Appalachian Trail near Wilbur Clearing Shelter. Turn right and follow the white blazes eastward toward Mount Williams, gaining the ridge and crossing a series of smaller summits with occasional outlooks. From Mount Williams, the Appalachian Trail heads south along the ridgeline toward the Mount Greylock summit area, entering spruce-fir forest as elevation increases. Skirt the observation tower and summit buildings, then rejoin the Appalachian Trail on the south side of the summit area. Use caution at the paved crossings for Rockwell Road, Summit Road, and Notch Road—watch for traffic and poor visibility in low weather. Continue a short distance on the Appalachian Trail, then veer right onto the Overlook Trail. After a brief traverse, turn left onto the Hopper Trail to begin the descent. Before completing the descent, turn right on Sperry Road heading north. At the Stony Ledge junction, transition to the Stony Ledge Trail a short distance, then Haley Farm Trail for the final stretch back to the trailhead. Water is typically available early in the route along Money Brook, but may be limited beyond the summit until late in the descent. This aggressive route includes sustained elevation gain, multiple junctions, and extended ridge travel—best suited for experienced hikers. The full circuit rewards with sweeping views from the summit and varied forest along one of the best alpine-style day hikes in Western Massachusetts.