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The Berkshires in western Massachusetts are a popular retreat for travelers from far and wide. The area is a summer home to the Boston Symphony Orchestra, Berkshire Theatre Festival, Berkshire International Film Festival, Jacob's Pillow Dance Festival, the Norman Rockwell Museum and Shakespeare and Company. While the arts opportunities are diverse and plentiful, the bucolic ambiance and rolling hills of the Berkshires are equally enticing. Nestled in the Berkshire Mountains is a private residence near Great Barrington, Mass. – named the best small town in America by Smithsonian magazine – whose owners have lived in the Berkshires for many years. Valerie Winig, RLA, principal of Wingate, Ltd., (Wingate) often assists her clients with landscape architecture design, though her firm is primarily a retail home furnishings store and interior design showroom. Such was the case with this property. Winig took on the project when the client asked her to oversee the project's landscape architecture after working as the client's interior designer. When Wingate became involved with the project, the residence had been built, the spa and pool placed, and the arborvitae around the pool area planted. Additional site development was incomplete beyond a desire for a rock outcropping near the residence to become a naturalized waterfall.
The client requested Wingate proceed on a design/build basis to avoid putting resources into extensive construction plans. The client had already established a water service design with Steve Mack of Foresight Land Services, Inc., of Pittsfield, Mass., that included permitting and construction observation of a gravity-fed springhouse located 2,000 feet away on a nearby hillside. The springhouse was intended to accommodate irrigation for the property, landscape water features for a proposed waterfall, and serve as a backup water supply to the house. Foresight's involvement, among other site engineering responsibilities prior to Wingate's involvement, included the pool foundation and pool drainage design.
Water Features Wingate's first design decision led to the displacement of an enormous rock structure in the middle of the rear yard. The rock formation, a hollowed-out oval approximately five feet in diameter, was relocated to the top of a rock outcropping. The reconstituted structure was transformed into a wishing well that doubled as the origin of the new waterfall. Conceptually, the water – containing any wishes made at its source – leaves the wishing well and makes its way over the rock outcropping waterfall, dips below grade and reappears at the pool fountains, spa and lower pond area below. A safety fence around the pool area and a walkway to the rear were incorporated through the proposed lawn terrace when the water design was complete. The walkway was placed immediately adjacent to the stone retaining walls directly beneath the residence, enabling the terrace to maintain its expanse.
Pergola & Pavilion The lawn terrace was designed as an area for games or tented events that offered access to the pool area below. Tiered stairs lead from the terrace to the pergola, and the pergola to the pool. Additional improvements included a radial pavement pattern around the spa, which created a fluidity and clear orientation from the pool area. The radial pattern also defined a line of sight through the new pergola, designed and built by Wingate, to separate and contain the pool area from the lawn terrace. The shade structure also created a sight line into the pavilion beyond.
Wingate worked with Michael Precourt of Charles J. Precourt & Son, Inc., of Sudbury, Mass., who prepared shop drawings for the placement of each piece of multi-color, thermal finished bluestone pavers that were to fit into the walkway scheme both around the pool and en route to the rear yard. Precourt also provided all of the stone caps used for the retaining walls and radius stair treads. Around the pool, orderly and architectonic stone walls were laid out at a uniform sitting height to define the space as a distinct exterior room. Various stonemasons on site built a combination of both freestanding and retaining stone walls, which were incorporated extensively throughout the property. Indiana Buff limestone was specified and cut with a smooth machine surface and rock faced edges to be integrated into the adjacent natural setting.
Plants Working with the client and Mountaintop Landscaping, Wingate specified plant materials for the property. The client's love of lavender was introduced in the form of Lavandula Hosta, Annabelle hydrangeas and Russian sage. Dogwoods, crabapples and an edge-defining boxwood in several locations created multi-seasonal appeal and maintain an extremely clean and formalized setting, in contrast to the natural theme in the adjacent spaces. The waterfall area was planted by Mountaintop Landscaping and filled with hostas, sedums and thyme, and cut leaf dwarf Japanese maples punctuate the connections between the retaining walls and the rock outcropping. The site development was enhanced by Tom Whalen of Whalen Nursery, Inc., Egremont, Mass., who placed large-caliper deciduous and evergreen trees throughout the project. Fifty-three 12'–13' dark American arborvitae were installed around the pool in total, creating a backdrop for the trellis and lounging area, designed and built by Wingate. Specimen trees that the owner requested for other areas were field-approved and positioned on site by Wingate and planted by Whalen Nursery.
The residence's architecture is now fastened to the land via stone retaining walls, appropriately scaled exterior rooms, terraces and plant material. The security fencing for the pool is obscured with careful placement beyond the evergreens and atop the ha-ha retaining wall below the terrace. Wingate also used Haddonstone freestanding planters aged with "stonage mix" to match the naturalistic theme. Outdoor residence side terrace furniture and umbrellas were from Janus et Cie, and poolside and terrace furnishings beneath the waterfall were provided by Brown Jordan.
The landscape provides a clearly defined sense of place throughout the seasons. In winter, the exterior rooms remain vibrant with evergreens and red berries. In spring, indigenous serviceberry, dogwoods and crabapples come ablaze. In the summer, Japanese maples, mountain laurel, rhododendrons, azaleas, hydrangeas and high bush blueberries can be plucked for tabletop bouquets or delicious dessert making. In any season, this Berkshire gem was worth all of the wishes and work that went into its creation.
Francisco Uviña, University of New Mexico
Hardscape Oasis in Litchfield Park
Ash Nochian, Ph.D. Landscape Architect
November 12th, 2025
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