Located southwest of the House, is a 7-acre wooded area looped by a carriage drive. Chauncey D. Stillman built the network of trails for his equestrian pursuits, and they were later expanded and used for carriage driving. After finishing the trails, Mr. Stillman collaborated in developing the Wilderness garden with landscape architect Evelyn Poehler.
Statues were installed and rhododendron and mountain laurel were planted in the existing wooded area. Hawks sitting on pillars framing a shallow pool with a vertical spout mark the entrance to the wilderness. English sculptor Peter Watts and Polish-born sculptor Josef Stachura created 16 statues during the late 1960s and 1970s that embellish the Wilderness.