The wooded landscape of the Glen contains remarkable evidence of human activity over at least 500 years. This wild place was once in part a managed woodland and in part an elegant garden reflecting 18th- and 19th-century taste. This is particularly the case in the area around the Ladies Linn.
The Glen has seen much tree planting. Although no longer standing, some of the first larch trees in Scotland were planted here in the early 18th century. Oak, yew and Scots pines dating from the late 18th century still exist. There are some hollow ways, tracks so well-used that they have been worn down below the level of the land around them.
There is evidence of water management for Killearn Mill within the Glen. The mill was powered by water from the burns that flow through the Glen. The largest is the Kirkhouse burn.
When the Killearn estate was sold in 1939, the Glen became part of the land purchased for house development. Housing was built up to the perimeter of the Glen (Elder Road), but the Council did not allow any building in the Glen itself. In 1979 the ownership was transferred from the owners to Stirling District Council at no cost. The area remains in public ownership.