Tobin has been interested in painting and drawing since childhood. Thomas Curtin, a very well-known landscape artist from Cambridge, Vermont, influenced him by giving him his first set of paints at the age of twelve. Tobin remembers standing beside his mentor for hours on end watching him paint when he was a young boy. He was very impressed with and stimulated by his artwork and always felt fortunate to have known Thomas Curtin. As an adult Tobin admired the work of many regional landscape artists. He attended the workshops of Rhett Sturman, a landscape painter from Morristown, Vermont. He has painted with well-known New England Landscape painter Charles Movalli of Gloucester, Massachusetts, as well as Fred Hines, a good friend and mentor from Johnson, Vermont. Each summer he also joins like-minded painting friends for painting sessions throughout the woods of Vermont.
 
He likes the solitude of painting by himself or with his daughter, Eliza Tobin, who loves fine art as well. By painting directly outdoors, Tobin sees things he would miss from just looking at a photograph. In particular, he tries to capture the landscape, the time of day, the season of the year, by the way the light plays on different objects. "I strive to paint the feeling of a place and particularly like painting in the winter, spring and fall," he says.
 
Tobin's work has been shown by many New England galleries and is in private and corporate collections across the country and abroad. Some of his accolades include First Prize for Oils in the Annual Northern Vermont Artist Association juried show in 1992 and 1995, as well as their Merit Award in 1994, 1995 and 1996. He was awarded The Grumbacher Award in Stowe, Vermont'sHelen Day Art Center "For Art's Sake" Show, as well as Best In Show for 1992 and 2000, and the Best In Oils award in 1992. In the annual NVAA show at the Bryan Memorial Gallery, he was awarded the Holbein Award in 1999.