STORY BY BENJAMIN LERNER
PHOTO COURTESY RITA McCAFFREY
Winooski, Rutland, Hartford, and the Rutland’ s Women’ s House— each offering transitional housing, support, and a tight-knit community where residents and volunteers live and learn together. Dismas of Vermont is built around a philosophy that embraces the importance of compassion. For Rita McCaffrey, the work has always been grounded in faith and community— a blend of practical outreach and spiritual calling.“ When someone is forgiven, we all feel better,” she reflected.“ People are yearning to be accepted. There’ s no magic. It’ s hard work for the formerly incarcerated each step of the way.”
Groundbreaking Advocacy
Before she became one of Vermont’ s most influential advocates for criminal justice reform, Rita McCaffrey was a teacher. Born in Lexington, Massachusetts, the youngest of five children, she studied sociology and education at Trinity College of Vermont before beginning a career in elementary education. But in 1974, a chance encounter with a family friend at Weston Priory set her on a new path.
Amazing Grace
How Rita McCaffrey built an enduring community of second chances through her work with Dismas of Vermont
When Rita Whalen McCaffrey of Weston and Rutland received an honorary doctorate from St. Michael’ s College in May 2025, the moment marked more than just a personal milestone. It was a recognition of a lifetime of service, with five decades of building pathways of societal reintegration for Vermonters returning to their communities after incarceration. As the founder of Dismas of Vermont, McCaffrey has spent her life championing reconciliation, compassion, and the belief that people with histories of incarceration can change when given a chance to rebuild their lives on a firm foundation of structure, dignity, and love. Since opening its first house in Burlington in 1986, Dismas has grown into a statewide network of five homes— in Burlington,
The friend, Father Art Kirwin, OP, a longtime prison volunteer, inspired McCaffrey and her husband, Francis“ Frank” McCaffrey, a respected attorney, to become involved.“ I just wanted to help out,” she said.“ I asked the superintendent if there was someone without family nearby that I could visit.” The superintendent hesitated— few women made such a request at the time— but eventually agreed. That first visit, to an inmate at the Rutland Correctional Center, would change her life.
Soon, Rita was organizing volunteers to teach decision-making skills to incarcerated Vermonters through the Rutland Decisions Program, adapted from a model developed in Pennsylvania and Massachusetts.“ Our whole thing was teaching,” she said.“ The program brought the community inside, breaking the isolation.” Through the years, the program expanded statewide from Burlington to St. Johnsbury, Woodstock, and St. Albans, uniting volunteers and inmates in shared learning. For McCaffrey, it became clear that the greatest need came after release: safe, stable housing and a welcoming community.
The Birth of Dismas in Vermont
In 1983, Rita and Frank traveled to Memphis, Tennessee, to train community volunteers through the National Association of Volunteers in Criminal Justice. There, they met Father Jack Hickey, OP, a Dominican priest and Vanderbilt chaplain.
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