John Frederick Kensett most likely began Rocks, Darien-Rowayton in the late 1860s, a period when the artist developed sparer, more open compositions. The painting depicts a spit of land in Rowayton, near Darien, that juts off the Connecticut coast into Long Island Sound. The work was formerly thought to have been executed at Newport, Rhode Island, but the topography closely relates to several works clearly identified as Connecticut scenes, such as the oil painting The Old Pine, Darien, Connecticut (Metropolitan Museum of Art, New York). Around 1867 Kensett purchased property near Darien and Rowayton on Contentment Island and subsequently built a studio there. The area seems to have had great personal meaning for the artist, as during this period Kensett made repeated studies from various vantage points on or near the island.

After Kensett's death Rocks, Darien-Rowayton may have been sold in 1873 during the sale of the contents of the artist's studio that took place at the National Academy of Design in New York. Jasper Francis Cropsey subsequently acquired the work, finishing and signing it with both his and Kensett's names in 1876.

The overall structure of the composition reflects the late work of Kensett, with a massing of rocks to one side balanced by a broad, open horizon on the other. The sense of light and space also recalls Kensett's work from the last years of his life. Cropsey's contribution's can be seen in other aspects of Rocks, Darien-Rowayton, such as the finely painted figures looking across the water. In addition, the soft green and orange coloring in the shrubbery along the edge of the rocks are reminiscent of the fresh palette that Cropsey favored.