Commissioned in 1915, the gardens at Rolling Ridge were the first independent project of then-upcoming landscape architect Fletcher Steele. Ethan Allen, owner of the 38-acre peninsula, specifically wanted Steele to layout the whole property and build the gardens first, taking advantage of the existing trees and views so that Allen could walk out on finished grounds the day he moved in. The lawns, house, gardens, and garage were all planned to be "properly related to the others," with the gardens creating "outdoor rooms" which led from the house to the lake.

Closest to the building and steps from the patio, a shaded lawn leads to the curved benches (Exedra) on the left and the Bowling Green on the right, which guides visitors to the Fountain. When in operation, the Fountain pool would overflow into a cascade and small pools, creating a path lined by six small fountains that brought visitors to the Boathouse. Although the Boathouse (also known as Sunset Lodge and the Tea House) burned in the 1980s, guests today can still enjoy the view with a picnic in the area now called Lakeside Landing.

Sadly, the main fountain is no longer in operation, as it was originally designed to draw water directly from the lake—a feat no longer possible today. Yet the gardens continue to preserve the essence of Steele's original vision, offering visitors a glimpse into the timeless beauty of early 20th-century landscape design. These current and historic spaces give a sense of the gardens' original grandeur and enduring possibility, inviting guests to walk the same paths that once captivated Ethan Allen over a century ago.