Many Gloucester, MA residents know David Montgomery as a third generation boat builder, who, for some thirty years, crafted one-of-a-kind pleasure boats; fishing boats; and the locally-famous fish-class cat boats.

What few knew was that David was also a fine artist, equally skilled in the mediums of charcoal and paint. In 2005, David put away his boat building tools and decided to become a full-time painter. Now instead of painting boat bottoms, David paints boats on canvas, often they are the very boats he built. David also is a gifted portrait artist, praised for capturing a likeness, as well as for portraying something of the character and personality of his sitter.  

His drawing is not just technically correct, he is able to imbue his work with an emotional quality that gives it a sense of life. The artist’s nature and deep appreciation of his hometown also comes through as there is a sense of stillness and quietude in all his work.

“Growing up in my grandfather’s boatyard, I have always had a love of the shapes of boats. At the same time, I had an innate love of painting, starting with my earliest exposures to Norman Rockwell and N. C. Wyeth, and later the harbor scenes of Emil Gruppé and paintings of John Singer Sargent. Now, after thirty years of building boats, I get equal joy out of rendering their shapes with brush and paint on canvas (and it doesn’t hurt my back),” says Montgomery.

“I feel very privileged to live in an area with such a rich artistic heritage, one that continues to this day, and to be able to paint with such great Cape Ann artists as Betty Lou Schlemm, Jeff Weaver, and childhood-friend David Curtis.”