The award winning landscape design of Rolling Ridge was done by renowned landscape architect Fletcher Steele. He began his work in 1915, creating a winding drive through native hemlocks and over rolling hills. Open Vistas gave guests several views of Lake Cochichewick. The dominating piece was a long bowling green, flanked vibrant by rhododendrons, leading to a 25 foot circular pool that overflowed into 3 cascading fountains. 

A series of smaller shell fountains led the way to a veranda & boathouse (which burned down in 1980) that now serves as a private picnic area overlooking the Lake. One half mile of shore trails gave guests tranquil spots to see heron, sunsets, and the gentle waves of the lake. The estate was awarded the H.H. Hunnewell Medal from the Massachusetts Horticultural Society in 1935.