Generally speaking, Martha’s Vineyard properties can be divided into two categories: quintessential New England seaside homes or up-Island hideaways surrounded by foliage lush enough to make Thoreau envious.

Traveling down the inconspicuous dirt road to Cathy Weiss and Ed Solomon’s home, you might assume you were entering the latter. Pine, oak, and beetlebung trees line the winding path. A dense fog settles over the peaceful landscape. On closer inspection, however, you realize that the property is, in fact, that rare Vineyard thing: the best of both worlds.

“On a nice day we actually have a view of the ocean,” said Weiss, who purchased the Chilmark home with husband Solomon in 2012.

The couple, who are now retired and principally reside in Philadelphia in the off-season, had been regularly traveling to the Island together since the late 1990s. Weiss began visiting on her own as early as 1980. What began as one-week stays quickly evolved into longer visits, prompting them to seek their own summer property.

“The year we spent three weeks here I had to leave the Island, twice actually, for business,” Weiss recalled. “We realized, ‘we can do this,’” she said of the required back-and-forth for her then-job as an executive director of a philanthropic family foundation and Solomon’s role in event marketing. “So we started looking and saw this house. It just made sense to be here all summer.” 

Chilmark seemed like an ideal setting for the next chapter of their lives, especially since they intended to spend more of their time on the Vineyard. In 2020, Weiss took over as board president of the Martha’s Vineyard Museum in Vineyard Haven, a role that requires a significant time commitment on-Island. 

This particular property offered numerous attributes they were seeking: it’s a short drive into the center of West Tisbury and onto Vineyard Haven, giving them the convenience of down-Island living, but would allow them to enjoy the quiet and seclusion of an up-Island home. Plus, it had enough space for them to easily host their daughter and her family during visits.

“It was at the end of the road, for one thing,” Solomon said. “So there’s no traffic that goes by here, nice view, and we liked the footprint of the house.”

“Sort of,” Weiss corrected with a chuckle. “It was a big enough house without being too big.”  Its proximity to the King’s Highway off South Road was also appealing. Their property connects to the ancient trail system that was formally designated as a path for movement of material and troops across the Island in 1704. 

“I think we could actually walk the Island on the trail system, just from our property,” Weiss said. “It’s right back there, which is kind of fun!”

Even so, it wasn’t perfect. Despite all the boxes their new Chilmark property checked on their wish list, it required several major improvements to meet their needs. The house, along with the guest cabin at the base of the hill, was built in the 1980s on four acres atop a ridge. It originally featured a subterranean garage, a rather closed floor plan, and a staircase directly across from the entrance to the home.

Since purchasing the property a little more than ten years ago, Weiss and Solomon worked with a team of experts to open up the space and capitalize on natural light. The whole process took nearly two years.
“We had never done this kind of renovation before,” Solomon said. “Let alone doing it here,” on an Island, which can present unique challenges.

Because part of the living space is underground – a puzzling architectural feature – much of the renovation was spent better protecting the structure. “This house was built subterraneously, which doesn’t make any sense on top of a hill on clay,” he said.

To absorb rain water, they installed a French drain around the entire house, ten feet down. Sealants were used throughout the basement, followed by the next major tasks: upgrading the electric system – the previous wiring was deemed inadequate for the house – and digging a new well.

Solomon described updating the water system as an adventure in itself. The original “haphazard” system, as he called it, included a well that supplied water to the cabin at the bottom of the hill. After the cabin tank was filled, water flowed back up the hill to the house. “Jerry-rigged might have been the word,” he said with a laugh.

Ultimately, Solomon and Weiss decided to dig a well closer to the main house. “Fortunately,” said Weiss, “it didn’t have to go down too far.”

Inside the home, plenty of changes followed suit. “The living room was always here. The master bedroom was always where it was. Everything else has been changed,” explained Weiss. “Every window, every door has been changed. We extended the deck eighteen feet.” The couple said that their architect’s decision to move the staircase from the entrance to the western corner of the house was “brilliant,” drastically altering their initial plans. “We didn’t lose a bedroom in the process,” Weiss said. “It always had five bedrooms. When we moved the staircase, that’s where the third bedroom had been on the second floor.”

They also spent time designing their kitchen from scratch, which they called “a dream come true.” The layout of the kitchen was flipped so that it would face the water. In the process, they created more storage space in the form of a pantry and built-ins created by Hans King – a “terrific luxury,” said Weiss. The space was finished with a second sink and an island with granite surfaces, which provides a sleek complement to the kitchen’s palette of blue and black hues.

Today, the dust from the renovation long since settled, an easy flow between the kitchen and living room allows for seamless access to the deck, its view unobstructed by sliding glass doors. The yard stretches out below, seemingly without end in the summer haze. Mid-summer blooms, courtesy of Jennie Slossberg of Garden Angels, dot the landscape. A half wall on the upper floor opens to a loft above the living room, while a semicircle window above the sliders provides a view from the elevated vantage point. 

Playful yet elegant touches – “Ed art,” as Weiss calls it – can be found throughout the home. One such piece is the collection of vintage electric insulators and antique irons peppering the shelves by the stairs. Another is the dining room table, the base of which is an old iron stove. A decidedly modern lamp hangs above the same table, a souvenir from Solomon’s office in Philadelphia.

The dining room chairs vary in shape, painted graphite-gray by Anne-Marie Eddy of Coastal Supply Co. in Vineyard Haven with hand-sewn cushions. Solomon’s desk upstairs was made from a detached barn door. 

Wares from the now-closed Midnight Farm store in Vineyard Haven add pops of rustic whimsy to the house, evident in unique pieces, such as a soda bottle chandelier above the stairs. A wooden table formerly belonging to Walter Cronkite, found at a Vineyard yard sale, occupies the common area on the ground floor. 

While so much of the house’s interior has been renovated – including the addition of several windows and even a few altered roof lines – the unchanged aspects of the structure are still evident. They kept the original beams in the living room, kitchen, upstairs, and master bedroom. Untouched also are the yellow pine floors in the master bedroom, which, Weiss explained, “really hold up!” 

Perhaps it comes as little surprise that the couple appreciates these nods to the house’s history. From her role on the museum board for the past few years, Weiss brings a unique perspective on the legacy of narrative on Island life. 

“When we live in a place like Martha’s Vineyard that has a public perception of what it is, it’s really important that you are grounded in what the reality is,” Weiss said. “It’s a fascinating, complex story that involves a lot of different people who came here in a lot of different periods for a lot of different reasons.”

This is abundantly evident in the artifacts in the house and the stories of their origins. Despite the hurdles of the renovation process, the house on the ridge has become, as Solomon said, “suited to our sensibilities and tastes.”

Said Weiss: “I love the ease of living here.”