Following the death of his father in a hunting accident, Tryon was raised in the East Hartford home of his maternal grandparents. At the age of fourteen, he and his mother moved back to Hartford where he worked for a short time in a gun factory before becoming a clerk and bookkeeper in a bookstore. He worked in this capacity for ten years, sketching and doing ornamental calligraphy on the side. After his marriage to Alice H. Belden in 1873, Tryon opened a studio in Hartford and took on several pupils. Three years later, he held a large sale of his work in order to finance a period of study abroad.
Tryon settled in Paris, where he worked for three winter seasons under drawing teacher, Louis Jacquesson de la Chevreuse. In addition, he sought criticism from Henri Joseph Harpignies and Charles Fran‡ois Daubigny. He remained in Europe for five years, spending time with Americans, Abbott Thayer, Robert Brandegee, and William B. Faxon. Returning to New York in spring 1881, Tryon took a studio in the Rembrandt Building and was elected to the Society of American Artists the following year. After two summers in Eastchester, New York, he chose South Dartmouth as his off-season residence, spending half of each year sailing and fishing there.
In 1885, Tryon took the position of professor of art at Smith College, Northampton, Massachusetts; he traveled to the campus to teach every three weeks until 1923. His work soon passed from a brief Barbizon-inspired period into his better-known tonalist phase. One such landscape won an Academy Hallgarten Prize in 1887, although the award was recinded when it was realized that the artist was over thirty-five years of age, and thus, ineligible.
An important event occurred in 1889 when Tryon met the collector of American and Oriental art, Charles Lang Freer. Over the next two decades, Freer amassed a large collection of his work, which passed to the nation with the bequest that established the Freer Gallery, Washington, D. C. Another significant group of Tryon's landscapes is located at Smith College, in the art gallery that Tryon endowed shortly before his death.