Provincetown Harbor also gave Jesse an opportunity to paint another of his favorite subjects, namely, boats and ships. There were always good examples of fishing vessels tied to the docks that projected out into the harbor. As well as painting boats with their sails down and snug to the wharf, Jesse also painted boats pulled up on the shore, either for repair or to get out of the tide.

When asked what type of pictures he preferred to paint, Jesse’s answer was lots of vivid color. Jesse learned to paint with oils, watercolors, crayon, and pastels. His most treasured possessions were his palette and painting box. Although he took many photographs for reference, Jesse always made unsigned sketches of his scenes. These were intended to capture the vividness of colors and the shadows that occurred during the changing light of the day.

Jesse painted miniatures for many of his friends, including individually painted Christmas cards, each an original. At one time there was interest in painting on candles, and Jesse was able to capture images even on a thin tapered wax candle stick. Another favorite of his was to paint wall scenes and window decorations in private homes. Jesse also worked for the Metropolitan Opera House and painted scenes as large as 37 x 70 feet. It was at this time that it became evident that Jesse could paint with his left hand as well as with his right hand. This was a real advantage when painting such large pictures.