North Sugarloaf Trailhead This moderately challenging 3.1-mile loop trail near South Deerfield takes an average of 1 hour 34 minutes to complete. The loop starts at the small parking area off Hillside Road and leads into Mount Sugarloaf State Reservation, winding through the forest to the summit of North Mount Sugarloaf Mountain with scenic views. The trail offers stunning views of the Connecticut River, Holyoke Range, and agricultural lands. North Sugarloaf Mountain is only accessible by foot; a small cave is located just beneath the summit ledges. Highlights include stunning views and well-maintained, dog-friendly paths.