Amelia Montague Watson is closely associated with two locales with distinctly different topographies: Martha’s Vineyard, an island off the coast of Massachusetts, and Tryon, a village located in the Blue Ridge Mountains of North Carolina. Born in East Windsor, Connecticut, she was tutored at home by her mother, an amateur painter. She studied painting in nearby Hartford with Dwight Tryon, whose Tonalist landscapes clearly influenced his young student. Watson evolved as a dedicated teacher, especially of women. In her early twenties, she joined the faculty of Temple Grove Seminary in Saratoga Springs, New York, and remained there several years, but eventually returned to her roots to teach at the Hartford Art School. 

Watson’s longest affiliation was with the Martha’s Vineyard Summer Institute, where she taught from 1878 to 1902. A promotional bulletin described her classes: “Lessons will be given in oil, watercolor, and pastel. The work will be carried on in all favorable weather out of doors, and will consist of making sketches of the many attractive bits of sea and landscape which the Island has to offer.” In her own work, Watson, primarily a watercolorist, met with considerable success. The actor and playwright, William Gillette was a major patron; he had gained an international reputation performing Sherlock Holmes and invited Watson to visit him in Tryon, a momentous experience for her. Soon, Watson began to spend winters in Tryon, which was an emerging art colony where other painters such as Lawrence Mazzanovich and George Aid settled in the 1920s. Like Martha’s Vineyard, Tryon was a seasonal destination for people with means, and those tourists frequently acquired her paintings. Around 1914, she built a studio/residence she called “Under the Tupelo,” which had a view of the nearby mountains. Louis Rowell was among the artists she mentored during her time there.

Using Henry David Thoreau’s classic travelogue, Cape Cod (1865), as her guide, Watson explored the island in 1895. While touring, she sketched and painted her own impressions which became the inspiration for a deluxe two-volume edition of Thoreau’s book. Published by Houghton Mifflin in 1896, the edition was an artistic and commercial success. Watson illustrated other books, including The Carolina Mountains by her longtime friend Margaret Morley. She frequently journeyed to Canada with her sister Edith who was a successful photojournalist. The two collaborated often, with Amelia hand coloring the photographs. The financial fallout from the Great Depression forced Watson to sell her home in Tryon; she moved to Florida to live with cousins, and continued to paint there as well.