When you meet the Bosharts—Greg, Cara, and their children Devin (16), Gabriel (14), and Alexis (12)—you quickly understand why their presence is felt so warmly throughout Dorset. Between their deep community involvement, their generosity, and their enthusiasm for making Dorset more beautiful and connected, they are the kind of neighbors who elevate the entire town. And at the center of much of that quiet leadership is Greg, whose vision and service have shaped the community in ways many residents enjoy every day.

The Bosharts moved to Vermont 17 years ago from the Washington, D.C. area, looking for a safer, more grounded place to begin raising a family. They first settled in Manchester, buying the very first home they toured, and later moved just one street away into Dorset. The move was so local, in fact, that Cara famously traveled to the new house on her lawn mower.

Greg, a native of the Adirondacks, had long felt pulled toward life in New England. After completing six years of service as a U.S. Army Black Hawk pilot, he earned his Bachelor of Architecture from Syracuse University and immersed himself in the design world in Georgetown. When he and Cara married, Greg carried a dream of designing homes in a place where sustainability, natural beauty, and craftsmanship truly matter.

Today, Greg owns Maple Valley Design Build, one of the region’s most respected residential design and construction firms. He is licensed in Vermont, is a LEED Accredited Professional, and is an active member of the AIA and NCARB. His work is known for blending artistry with environmental responsibility, and his homes often reflect the same sense of welcome and warmth that he brings to his personal life.

But Greg’s contributions go far beyond his profession. A natural servant-leader, he has become a steady presence in town life. At First Congregational Church, he oversees facilities, ensuring the historic building remains a place of comfort and community. He has served as chair of the Manchester Planning Commission, consistently advocating for thoughtful, responsible growth. His Saturday morning Cars & Coffee gatherings provide a fun, informal space for neighbors to meet and connect. He even opened his office doors to host monthly New Canaan Society meetings, supporting the spiritual and relational lives of local businesspeople.

And when the town or a nonprofit needs help—design guidance or simply someone reliable who shows up—Greg is often among the first to answer the call. His pro bono design work for the newly renovated Manchester Community Food Cupboard is just one example of the many ways he quietly strengthens the community behind the scenes.

Cara, in her own right, brings tremendous heart and leadership to Dorset. A Virginia Tech horticulture graduate and former urban forester, she owns Flowers by Cara, a floral studio known for its artistic event work. She serves as president of the Community Food Cupboard board, sits on the Dorset Field Club board, and is a deacon at church. Her knack for bringing people together has made the Sunday potlucks she organizes at the Field Club a beloved tradition. This year she even spearheaded a group of local women to design and install fresh holiday decorations throughout Dorset—one of many ways she infuses the town with beauty and joy.

Their children reflect their parents’ strong sense of purpose and community. Devin and Gabe attend Burr and Burton Academy; Devin competes on the Varsity Bass Fishing Team, volunteers with the Manchester Fire Department, and works two jobs, while Gabe helps lead summer church programs and contributes drone photography to Cara’s floral events. Alexis dances, plays basketball, participates in Girls on the Run, and joyfully runs the Sunday coffee hour at church.

The Bosharts often say their favorite part of Dorset is the generosity of the people—how neighbors show up for one another without hesitation. Yet what many locals might say in return is that families like the Bosharts are the reason Dorset feels the way it does: connected, welcoming, and full of heart.