In 1912, at the age of 47, John Benson placed his painting The Outer Rocks in an exhibit sponsored by the National Academy of Design in New York City. That show marked the first of what would come to be a regular outlet for John Benson's artistic talents. During the years he spent in New York as a full-time architect, his marine works of art were displayed in numerous exhibitions in New York, Philadelphia, Boston, and Nantucket. The Kennedy Galleries in New York were his primary sponsors.

After retiring to Kittery, Maine, in 1925 to pursue his lifelong passion of painting, John Benson switched his exhibition venue to Boston, where he became active in the Guild of Boston Artists. That organization sponsored exhibitions of his work with great annual regularity, all through the late 1920s, the 1930s, and the 1940s, ending with a Memorial Exhibition in his honor in 1948, a year after he died.

During the 40-year period after his death, Mr. Benson's paintings were shown at the Bristol Art Museum in Bristol, Rhode Island, the Peabody Essex Museum in Salem, Massachusetts, and the Kittery Historical & Naval Museum in Kittery, Maine. Two very recent exhibitions have reawakened a vigorous interest in this talented artist. In 2004, the Portsmouth Athenaeum in Portsmouth, New Hampshire, hosted a very popular one-man exhibit, attended by record numbers of guests during its four-month run. The most recent exhibition, summer 2006, at the Maine Maritime Museum in Bath, Maine, was seen by thousands of visitors, and delighted museum staff members as well.

In his lifetime, John P. Benson had his paintings shown in more than 40 exhibitions. A small sampling follows. For more information on his many exhibitions, refer to the chapter in Volume II.

1912 - National Academy of Design winter Exhibition, New York City
1923 - Kennedy & Co., New York City
1924 – Marblehead (Massachusetts) Arts Association – August
The first annual exhibition by this organization was reviewed by The New York Times, which commented that “it was appropriate that the first painting in the catalogue, No.1, should be a yachting scene, a large oil, small boats in soft tones, by John P. Benson.”
1931 - The John Levy Gallery, New York City
1931 – Addison Gallery, North Andover, Massachusetts
John Benson noted that Trading Schooner was listed as being for sale at “$500 gross.”
1932 - Doll & Richards, Boston
1936 – Portland, Maine, Society of Art
John Benson’s The Discoverers was “given the place of honor in the annual spring show” at this Portland exhibit, according to The Kittery Press of March 20, 1936.
1937 – Community House, Kittery Point, Maine – July
Works by John Benson and Russell Cheney, both residents of Kittery, were exhibited during a house tour in Kittery to benefit the local Girl Scout Council.
1937 - Art Week Show by Jordan Marsh Company, Boston
1937 - Corcoran Gallery of Art, Washington
1940 - Portland Society of Art, Portland (Maine)
2004 – Portsmouth Athenaeum – June to October
2006 – Maine Maritime Museum, Bath, Maine – June to October
26 oils, two etchings and one watercolor were exhibited. This one-man show of primarily Maine-based paintings was augmented with various memorabilia from the John Benson Archives.