Crotched Moutnain Loop

The route begins at the Bennington Trailhead on Old Greenfield Road in Bennington, New Hampshire. From the trailhead, follow the Bennington Trail eastbound as it climbs steadily through mixed hardwood forest. After a gradual start, the grade increases and the trail becomes rockier as it approaches the upper mountain. Near the summit area, short, rough sections require careful footing, especially in wet or icy conditions. Open ledges near the top provide broad views toward the Monadnock Region and, on clear days, the Green Mountains. After reaching the summit area, continue east on Upper Link Trail and connect with Summit East Trail. Follow Summit East as it curves south across the upper slopes, then turn onto Old Mountain Road heading west. Continue past the junction with Summit West Trail, staying on Old Mountain Road, and then take the Lower Link Trail downhill to Shannon’s Trail. Follow Shannon’s Trail north as it descends through quieter forest and eventually reconnects with the Bennington Trail. Turn left and retrace the Bennington Trail westbound back to the trailhead. With limited water, exposed ledges, and frequent wind near the summit, preparation is important, but the route delivers a varied and rewarding day hike on one of southern New Hampshire’s more scenic ridgelines.