Jewell Hill Loop

This easy route begins at the main parking area on Crocker Road, just before the pavement turns to dirt. Follow Jewell Hill Trail west through gentle forest before turning left onto South Loop Trail. As the trail winds through open meadows and wetland edges, turn left onto Laurel Lane for a short distance before rejoining Jewell Hill Trail and climbing toward the high point of the property and its namesake. At the summit of Jewell Hill, a short spur leads to Hudson Overlook, where broad views take in Mount Wachusett and, on clear days, the Boston skyline. From here, descend via Olaf’s Run through forested slopes, then turn right onto Crocker Farm Trail to return to the starting point. For a longer outing, hikers can add side trails like Fox Pasture Trail or Willard Trail just south of Crocker Road. This property, protected by The Trustees of Reservations, crosses former farmland and includes historic farm structures. Trails are open year-round for hiking, snowshoeing, and cross-country skiing. While well-maintained, trails may be muddy or icy in wet seasons. Dogs are allowed on leash, and hunting is permitted in season (except Sundays), so wearing blaze orange is recommended in fall.