“We offer a different level of involvement in the design process, working closely with the homeowner on the design and being involved in the construction process to create a bespoke outcome.”
— Wenonah Webster, principal and creative director, Webster Landscape
“The term ‘landscaping’ is often associated with mowing and weeding, not gardening and design work,” Wenonah Webster of Webster Landscape (93 Ashley Falls Road, Sheffield) clarifies. “People can decide to landscape or steward their land back to health and biodiversity. We start from the structure, and our goal is ultimately about ecology—to heal and elevate the local landscape, bringing it more in line with the greater ecology and sense of place.”
Asked how that ethos plays out, Webster describes the company’s holistic approach: “When we first visit a property, we listen to the client and to the surroundings—looking at the distant hills, seeing which plants already exist in the area, and taking this into consideration in a way that heals and nurtures the land. Once we start building our design, it’s not about decorating but about enriching through thoughtful structuring, planting, maintaining, and stewarding our gardens into maturity.”

No stranger to living on the land
Webster received an early introduction to living on the land, having been raised on a commune in Lewis County, Tennessee, approximately 60 miles southwest of Nashville. According to its website, The Farm is an intentional community based on principles of nonviolence and respect for the Earth. It was founded in 1971 by Stephen Gaskin and hundreds of spiritual seekers from San Francisco, who promoted work and service as a path to a meaningful life and a positive impact on the world. (Today, it functions as an eco-village and model of sustainable living.) “My parents moved with friends to The Farm when I was four. There were 1,500 people living on 1,000 acres. It was very much an experience of how to live with others in the world,” she shares. “It was also a unique opportunity to look at business in a different way, that’s about supporting the community as a whole.”
“I grew up around heavy equipment with my dad (often holding the stick while he took transit shots for grading) and working in the garden with my mom,” Webster explains—the perfect training ground for running her own business one day. “That’s very empowering as a woman in the construction business,” she admits. “I feel very comfortable in that space. I enjoy working with the contractors so much.”

For a while, she tried to escape the dirt, experimenting with fashion and graphic design in college. When she took a drafting course and began to understand the psychology of space and structure, she discovered her passion, paving the way for her to earn her degree in architecture from the Massachusetts College of Art and Design in Boston. Glassblowing was another obsession she explored after college. “I worked on the glass team of Mark Winer at Martha’s Vineyard Glassworks, which was intense and fun. I was the only woman in the hot shop and was simultaneously working with a chef at a restaurant across the street. Along with my background doing floral installations for weddings, not much can throw me off,” she claims.
Moving back from Martha’s Vineyard to Hudson, Webster returned to landscaping and floral design, working with floral designers Pamela Hardcastle (New Marlborough) and Ariella Chezar (Egremont) on large weddings. Soon after (in 2005), she launched Wenonah Webster Design. “It was an amazing opportunity being in Hudson. I found lots of clients, providing hands-on project management from design to install, working with subcontractors to build each project, and seeing them through to completion.”

Living in Hudson for nearly the first decade of running her own business, she became much more mobile, taking on three major clients in the restaurant industry, which required regular travel to California and living out of a suitcase for five years. “That was the best thing that ever happened to me. The experience gave me great exposure to fascinating, fun, amazing people and affirmed that I was on the right path,” she recalls. “I spent a lot of my time asking questions and seeking out the best people in the field. Being surrounded by such big minds forced me to define and exceed my limitations.”
Adding “heavy muscle” with Webster Ingersoll
“Mark Winer, Pamela Hardcastle, and Ariella Chezar were all extraordinary teachers,” Webster acknowledges, but what influenced her most was watching her father, Ben Webster, run a company that was groundbreaking in our area at the time. “My dad joined forces with Tom Ingersoll to take on a full historic renovation of the landscape at The Mount. I was lucky to watch this transition and later work with him for five years,” she says—an experience she describes as “a really good run.”

What made Webster Ingersoll groundbreaking was the fact that it was the first time everything was done “in-house with some heavy muscle,” Webster notes. While there, she partnered with some of the top landscape architects in the Northeast and was able to observe their process, gaining a good understanding of what was involved.
When her father split amicably with his business partner in 2012, he rebranded as Webster Landscape. In 2017, when she was 37, Webster decided it was time to stay in one place and moved to Sheffield, continuing her own design practice and mainly working with clients in Hudson. “My dad was working on seeing how he could pass this company on, and he approached me. I said, ‘Absolutely not, thank you!’” she admits, adding that she thought the business was too big.
“Then I looked at how I work, starting on the ground, sketching the design on paper, going back to check on things, and staying in touch with the construction process, and realized that the model was very enticing,” she explains. “I had so many ideas about how we could do more in-house, including how we could have refined design tied to exceptional construction, and how that process would create a timeless and beautiful outcome for clients that went well beyond what a handoff design could do.” And so, her answer changed.

“What inspires me most about our design work is achieving the biodiversity needed to sustain healthy native pollinator habitats within a very modern or formal design. Taking environmental goals into consideration does not mean sacrificing design integrity; in fact, it makes that stronger.” Webster also believes in the importance of engaging contractors and tradespeople in the design process, bringing clients and contractors together as a team. “I love this process, and not many are doing it to this level due to the equipment and infrastructure I signed on with in taking over Webster—trucks, crews, excavating, and administration—and the architectural, structural, and plant knowledge needed to create a holistic design.”

Design, build, install
Webster emphasizes that the company is a one-stop shop, offering a comprehensive package that includes designing, building, and installing. “Being an employer and a chief operating officer, I knew that design generated more income than construction. I also knew that we could all benefit from combining the two, leading to steady growth with competent professionals to support our team.” This model involved shifting the way they approached jobs—slowing things down, allowing more time for planning, and operating more like a construction company with real-time project tracking. “We’ve learned to keep things super tight,” she says.
Coming in at the end of most construction projects, when people have spent their money, can present challenges. “Clients ask, ‘Can we get this?’ And the answer is, ‘Yes, there is value in doing less, doing it well, and we’ll do it over a period of time.’ The integrity of our work is important; we’re not willing to sacrifice quality,” Webster states.
Recalling the first five years, she says she was focused on transforming the business into something she wanted to steer, shifting the company’s focus from construction to design and project management. “It was challenging,” she admits. “Now we’ve become a smaller, tighter, more efficiently run team that focuses on what we do best—the finishing touches—everything from subgrade to planting, general contracting with heavy equipment, masonry, and stonework.”

Sustainability, first and foremost
“Inherently, our design process is always driven by the history and ecology of the project—listening deeply to the client, clarifying their goals, looking at the land and getting a feeling of what already exists there (shale and bluestone for N.Y., granite for Conn., Goshen for Mass.). All of that guides us from the beginning,” Webster says, adding that they use plant material structurally and in a refined way to heal the disturbance made by construction.
All of this requires a lot of science. And sometimes, the heavy native-focused planting can be hard to maintain. “I use natives in a way that (because they’re hardy) allows them to have long seasonal value and die well, meaning they remain interesting even after they bloom. They take less maintenance if used correctly and look like they’ve been there forever,” Webster shares. In turn, the design has a timeless quality, elevating the experience of the surrounding landscape.
Committed to team building
Continuity is key to the company’s success, as the same team has been working together for four years or more. “We’ve created a real community here,” Webster beams. That team encompasses five sectors—design, construction, horticulture, project management, and administration—all of which are closely intertwined. “Previously, no one knew what the other members of the team were doing, which created angst. Now we circle up every Friday, put up all the work that’s happened that week, face each other, and listen—all one unit, everyone having equal value.”

Over the years, the company has been able to increase its margins as it has added employees; however, Webster acknowledges that employing people is challenging for a small business committed to offering job security and benefits to help offset the region’s high cost of living. “Having 10 to 11 employees on board doesn’t necessarily mean that we’re taking on a lot more work; instead, that allows everyone to have more flexibility and fun doing what they do,” she clarifies. For example, they generally have four or five projects per season for their in-house construction team, while the design and project management team (which includes architects, builders, sitework supervisors, and subcontractors) has 10 construction projects per season.
“We schedule the whole year at the beginning of each season, so the entire team knows what they’re doing in any given month. And I rely on our CFO to keep challenging us to get better at what we do financially and become more savvy, which is a major learning curve for me,” she shares. What was once her father’s business adventure is now hers, and Webster couldn’t be happier. “This adventure has taken us to a place beyond my ideas and dreams.”





