Sleepy Hollow Painter Brings Creative Support to Sing Sing, County Jail

Jane Hart stands beside a poster from a lecture she gave on art therapy at Sing Sing Correctional Facility. Photo by Robert Brum

On her first day leading an art therapy session at Sing Sing Correctional Facility in Ossining, Jane Hart didn’t know what to expect. 

“About 12 men filed into the room and sat down at two tables and I thought, ‘I’m smaller than all of them so I’d better talk loud,’ and I did,” Hart recalled. “I explained that this is meant to help you manage difficult emotions and feel better.” 

She laid out the rules to the men incarcerated in the prison: Work in silence, share materials, don’t say anything negative about anyone else’s artwork or your own. You can talk about your work afterward, but you don’t have to. 

“I looked at some of them and they had already started,” said Hart, herself a painter. 

Hart had asked Sing Sing officials to allow her to start the program, which she said became the first of its kind in a New York State men’s maximum-security prison.  

“I was surprised to see that the incarcerated men, not only were just like anybody else, but they were very open” to expressing themselves through art, she said of her volunteer work at Sing Sing. “There was never an issue” of her being a woman in the men’s facility. 

Jane Hart holds her acrylic painting Winter Water Skiing. Photo by Robert Brum

Hart was subsequently hired some five years ago by the Westchester County Department of Correction to bring art therapy into the county jail for men and women incarcerated there. 

Her experiences working behind bars dispel stereotypes some may hold about people in jail. 

“I had no preconception,” said Hart, 79, during an interview on the terrace of her apartment at Kendal on Hudson, a retirement community in Sleepy Hollow. “I did not know what to expect, and I think my feeling about the people I work with is very positive. I find them cooperative, willing to delve into their feelings and express them, so there’s trust. I think that there’s two elements that are most important: Mutual respect and mutual trust.” 

The work she does “is meant to give them a resource so that, especially when they get out, they will know that when they’re feeling very anxious or depressed or angry, they can go to their art supplies, even if it’s just a pad and a pen.” 

Hart added: “We don’t talk about their crimes. I’m not told and I don’t ask them. They have already been judged, or they’re going to be judged. That’s not my job. My job is to support their creativity, which in turn supports them and their well-being. I think a lot of them are repentant and really want to do well when they get out and have a better life.” 

To pursue a master’s degree in art therapy, the former Bronxville resident left behind a career as a journalist and author that included writing the Pulitzer Prize-nominated book, The Hidden Children: Secret Survivors of the Holocaust. 

“I decided I had enough after the book, so I changed gears,” she said of getting her master’s, which she called “a gift for me because of my own painting.” 

Hart works in oil, acrylics, pen and pencil, calling her art “not exactly cartoons. They’re whimsical but they’re full of emotion, too, and full of fun.” 

Her next challenge is finding a gallery to represent her paintings. Hart’s artwork is currently displayed through Oct. 28 as part of an exhibit titled Sugar, Sweat & Stone: Art & History at Hastings-on-Hudson Village Hall, 7 Maple Ave.  

Visit and to view Jane Hart’s artwork.


  1. Thank you, Jane Hart, for starting this art therapy program at Sing Sing. Your whimsical outlook must inspire the incarcerated to free their spirit and create their own works of art.

  2. I would have given anything to have been a fly on the wall at one of your prison sessions! You were a gift to them as you are to us here at Kendal.

  3. Jane, we are thrilled to see you getting recognition for the good works that you do. We know of many other acts of charity that you do that are not covered in the Sleepy Hollow article. You are kind, thoughtful, talented and so generous with your time. You’ve made the lives of others better…what a great legacy.

  4. Congratulations on your work with the incarcerated … you make a difference and should be very proud of the work you doing.

  5. Jane Hart, is such a wonderful artist, I had the privilege of knowing her, from My employment at Kendal, I loved her pieces of art, I could compare her furniture art as whimsical, so MacKenzie child like, Alice in wonderland, but this is Jane in wonderland, her love of animals and art,connected us,I miss being a part of the Kendal life..

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About the Author: Robert Brum