Community Corner: Dr. Gary Bailey on Connection, Commitment, and the South End
Interviewed by Irwin Levy, Friends of Titus Sparrow Park Board Member
Welcome to this month’s Community Corner, where we shine a light on neighbors whose spirit, service, and heart help make the South End such a special place to call home.
This month, we’re featuring Dr. Gary Bailey, a longtime resident, educator, gardener, and advocate. Through his leadership in social work and education, his civic involvement across Boston, and even his daily walks through the neighborhood, Gary brings a deep sense of care and connection to the community.
When I reached out to Dr. Gary Bailey for this month’s Community Corner, he replied, “It would be best if you take the lead on this given my crazy schedule and time demands.” As I took a deeper dive into Gary’s professional career and community commitments, I quickly understood his request and realized that the limited space of Community Corner can only begin to capture the scope of his contributions.
A Career of Leadership and Learning
Gary currently serves as the MSW Program Director at the Simmons University School of Social Work, where he is also a Professor of Practice in both the Schools of Social Work and Nursing and Health Sciences.
His early career was as an Elder-at-Risk social worker at Family Service of Greater Boston. Interestingly, the South End was part of his catchment area. He has since dedicated his work to sharing his knowledge, expertise, and leadership across social work, public health, youth education, and affordable housing—fields united by a commitment to social justice and community well-being.
Originally from Cleveland, Gary moved to Boston to attend Tufts University, where he earned his BA in Child Study from the Eliot-Pearson School. He later received his MSW from Boston University and an honorary Doctor of Humane Letters from the University of Connecticut.
Arts, Gardening, and Creative Renewal
An avid gardener, Gary tends his own plot in the park and recently took on caring for Union’s new plot as well. A passionate supporter of the arts, he proudly identifies as a “culture vulture,” with a love of music, dance, and theater across all genres. He serves on the Board of Advisors for the Celebrity Series and can often be found exploring Boston and New York’s museums. Once a month, he takes a brief “art retreat” to New York City, 36 hours devoted to exhibitions, performances, and creative renewal.
Champion for Youth and Civic Engagement
Gary’s advocacy for youth education runs deep. He serves as Vice Chair of the Massachusetts Educational Financing Agency (MEFA), President of the Board at Fenway High School, and a mentor in the Diversity Scholars Leadership Program at Boston University’s School of Public Health Center for Excellence.
Within the South End, his civic engagement includes serving on the boards of the South End Library and the Friends of Harriet Tubman Park, and he was on the board of United South End Settlements until June 2025. A longstanding member of Boston’s historic Union United Methodist Church, Gary chairs the Church Council and serves on its Leadership Team. And yes, he’s also on the Board of the Friends of Titus Sparrow Park!
Rooted in History and Community
A South End resident for more than 20 years, first on Dartmouth Place and for the past eight years on Columbus Square, Gary is well known for his early morning walks. Every day, through all seasons, he walks for three hours before work, describing it as a vital practice for his physical and spiritual wellness: “It’s sometimes the only time in the day that actually belongs to me.” He explains that each hour has its own focus, the first is meditative, the second centers on mindfulness, and the third prepares him for the challenges of the day ahead.
Reflecting on the neighborhood, Gary recalls a different South End, from its jazz-era past to when it was the epicenter of LGBTQ life in Boston. He is deeply committed to celebrating and preserving the area’s rich, diverse history. “There is a richness that comes when a community honors the variety of experiences and histories that make it what it is and that made people want to be part of the neighborhood vibe.”
Gary’s dedication to education, service, and the arts reflects the very best of what makes the South End such a vibrant and connected place to live. His deep commitment to community and to the people who shape it serves as an inspiration to all of us who call this neighborhood home. When asked how he manages to do so much, Gary credits his upbringing: “I was raised to be productive and engaged in my community,” he says. “If you want something accomplished, ask a busy person.”
