Truro Vineyards, Gelato Joy, and Thomas A.D. Watson and Francie Rudolph on raising their families and growing their businesses in towns defined by seasonal extremes.

by Maria Allen

Photographs by Julia Cumes

With miles of pristine ocean coastline, idyllic village centers and fresh-off-the-boat seafood, it’s no secret why the Cape’s outermost towns attract thousands of tourists each summer. As the seasons change and the crowds depart, life goes on at a slower pace. 

Year-round residents are the fibers that bind these seaside communities together. Some Outer Cape families have deep roots that go back for generations. Others are washashores who made a conscious decision to move here, trading suburban convenience for a tight-knit community where everyone knows your name. They all have a unique story about how they fell in love with the landscape and the lifestyle. No matter how they got here, these individuals know how to ride the wave of a seasonal economy and usually appreciate the silence and solitude of Cape Cod winters almost as much as the hot and hazy days of summer.

A Labor of Love at Truro Vineyards

David Roberts Sr. was riding his bicycle down Shore Road in Truro one morning in 2007 when he stopped to say hello to the owner of Truro Vineyards and learned of their intention to sell the business. Newly retired from a 40-year career in the fine wine and spirits industry, the former CEO of United Liquors knew it was an opportunity he couldn’t pass up. 

Roberts had been vacationing in Truro for close to 50 years. He envisioned the winery as a practical next step in his career, and more importantly, he saw it as a chance to bring his children together as part of a family-run business. Roberts proposed the idea to his wife and children, who at that time were spread out across the country. 

“It may have been my idea, but I made it clear to my kids that this was going to be their deal,” says Roberts, who now lives a mile away from the vineyard. His youngest daughter, Kristen Roberts, and son, David Roberts Jr., both signed on to be part owners of Truro Vineyards and made the move to the Outer Cape to begin making their dream a reality.

Kristen serves as CFO, runs the front-of-the-house, and manages wine tastings and special events, while her brother, David Jr., oversees winemaking and production. He works closely with head vintner Milan Vujnic to craft a variety of artisan wines. Thanks to his background as a beer brewer, David Jr. also helped to expand the family business by launching South Hollow Spirits, a new onsite distillery, in 2012. 

Truro Vineyards is a bucolic setting with five acres of grape varieties—Chardonnay, Cabernet Franc, and Merlot—nurtured by Truro’s sandy soil and salty sea breezes. Visitors from around the world come to sip wine and spirit flights and purchase signature blends in lighthouse-shaped bottles.

The decision to move to the Outer Cape was a leap of faith for Kristen and David Jr., but they don’t regret their decision. Both are raising families here and appreciate being able to send their children to local elementary schools with small class sizes. They’ve also found the business community to be incredibly supportive. “When you live out here, you learn to lean on one another,” says Kristen. “On any given day, I know there are 20 people I can call if I need something, like $1 bills for the cash register or extra cocktail sauce.” The family makes an effort to support other local businesses, too. For example, South Hollow Spirits’ signature spiced rum is made using spices from Truro’s Atlantic Spice Company, which is headquartered just down the road.

It was an experiment to see if there was enough need for a winery to be open on the weekends. People weren’t busting down the doors, but we had enough of a year-round community for it to work."

— Kristen Roberts

Truro Vineyards started staying open year-round two years ago, which was a risk given how quiet the region’s winters can be. “It was an experiment to see if there was enough need for a winery to be open on the weekends,” says Kristen. “People weren’t busting down the doors, but we had enough of a year-round community for it to work.”

As one might expect, the COVID-19 pandemic forced the family to re-envision some aspects of their business plan. Guests now enjoy their food (courtesy of the Blackfish Restaurant Crush Pad food truck) and drinks while seated at tables that are spaced 15 feet apart, rather than walking around the grounds with a glass in-hand. “It actually makes for a more intimate experience,” says Kristen. “It’s safe for our customers and it works for us.”

Taste of Summer inside Gelato Joy

Wellfleet is known for having a laid-back vibe, where kids are as likely to spend their afternoons surfing as hanging out at the skatepark. Local businesses and restaurants cater to a well-heeled summer clientele in search of experiences that capture the essence of summer. 

For Sandy Valli and her husband Leif, who owns a property-management company, opening Gelato Joy Cafe in downtown Wellfleet was part of their long-term retirement plan. The parents of six children between the ages of nine and 24, their goal was to create a seasonal business where their teenagers could help out during the summer months, while allowing the parents free time in the off-season for traveling. 

After a quiet opening in July, Gelato Joy quickly became a local favorite, serving up a rotation of fruity sorbets and decadent, all-natural gelato flavors, such as hazelnut, pistachio, and salted caramel. The cafe is located down a narrow alleyway, behind SICKDAY Surf Shop and the gift shop Drift. Valli’s brother-in-law, Olaf Valli, owns the building and is the brainchild behind the SICKDAY brand, a name that refers to a carpe diem mentality. (If the waves are good, surfers call in a “sick day” and head to the beach.) Ironically, fall and winter are the seasons when locals do the most surfing in this neck of the woods. “They’re the only ones that go toward the water during a storm,” says Valli. 

Each season has an awesomeness to it.

— Sandy Valliwho is glad her children have been able to grow up surrounded by nature.

There is a timeless beauty to the Wellfleet landscape throughout the year, thanks in large part to the protected lands of the Cape Cod National Seashore. “Each season has an awesomeness to it,” says Valli, who is glad her children have been able to grow up surrounded by nature.

“Wellfleet is a great place to raise a family, as long as you’re willing to drive,” says Valli. Whether transporting her daughter Anika to ballet class or son Burke to crew practice further up Cape, Valli views car rides as a chance to spend more time talking with her kids. Similarly, being able to work closely with her older children at the gelato shop has been one of the biggest rewards. Her son, Tait, age 24, built custom countertops and outdoor benches for the cafe and her daughter, Kenna, age 19, handles their social media accounts and helps out as an evening manager. 

Inspired by the multigenerational gelaterias in Italy, Valli hopes her family’s new business will help to bring other families together to share a sweet moment in their day. “We have a large family so we can’t always afford to all go out to dinner,” says Valli. “But we love to go out for ice cream together.” 

Beautiful Horizon for Thomas A.D. Watson and Francie Rudolph

Home to America’s oldest art colony, the Outer Cape has been a destination for fine artists and collectors for generations. Intimate galleries and studios pepper the main streets and back roads of these quaint seaside towns of Provincetown, Truro, and Wellfleet. 

“The light out here is pretty extraordinary,” says Truro artist Thomas A.D. Watson, who is known for his representational landscape paintings of the area. “There is so much national seashore and wild water. It’s an incredibly beautiful place to live.” 

Watson and his wife, Francie Randolph, a mixed-media artist and former Harvard professor, moved to Truro in 1998 after falling in love with a 200-year-old farmhouse with a small orchard and a two-story barn. The original deteriorating barn was replaced with a new post-and-beam structure that now houses Watson’s art studio on the upper level and Randolph’s studio below.

Watson was born into a family of artists—his father was a skilled illustrator, his grandfather was the founder and editor of American Artist Magazine, and his mother was a celebrated children’s book author. His childhood was split between Vermont and Truro, where he spent a great deal of time outdoors and the creative influences of his family and the surrounding community inspired his own artistic leanings. A graduate of Rhode Island School of Design, Watson’s landscape paintings depict the Outer Cape’s dramatic sand dunes and churning seas with stirring emotion.

Randolph’s nature-based artwork combines digital technologies with painting, photography, and printmaking techniques. She previously taught at Harvard University’s Visual and Environmental Studies department before moving to the Cape and turning her attention to the local food movement. Randolph co-founded the Truro Agricultural Fair and shortly thereafter the nonprofit Sustainable CAPE. “Our mission is to celebrate local food while teaching about the health of our bodies, community, and environment,” says Randolph, who helps oversee the organization’s farm-to-school program as well as the Truro Farmers’ Market. 

When they aren’t busy creating art, Watson and Randolph enjoy a down-to-earth lifestyle, spending their days gardening, swimming, and going on fishing trips with their son and daughter. One such outing into Cape Cod Bay inspired Watson to begin painting commercial fishing and lobster boats. The local fishing industry is an important part of the heritage of the Outer Cape and Watson’s images pay tribute to this local history. Earlier this year, his painting of a vessel known as the Joan ~ Tom was featured and auctioned off at the annual Provincetown Portuguese Festival.

Our mission is to celebrate local food while teaching about the health of our bodies, community, and environment.

— Francie Randolph

Somehow, while the rest of the world becomes increasingly dependent on their high-speed digital devices, Watson and Randolph have found a way to embrace life’s simple pleasures. “The rhythm of the seasons has been really wonderful because it gives us a lot of quiet time to do our work,” says Randolph. “We have a beautiful hearth and in the winter we will gather as a family in the living room and read books at the end of the day.” 

Even during a global pandemic, Watson has found peace by painting his natural surroundings, and with every brushstroke, he is continuing a local legacy.