In 1826 Casilear was apprenticed to the engraver Peter Maverick, a founding member of the National Academy. After Maverick's death in 1831, Casilear continued his studies under Asher B. Durand, and in 1832 he established his own banknote-engraving firm. He first exhibited in an Academy annual the following year, showing engravings. Casilear's career as an engraver flourished, but at the same time his interests in art grew to include landscape painting. In 1840 he went to Europe with Durand, John F. Kensett, and Thomas P. Rossiter. After visiting London he traveled to the Continent with Durand and passed the winter of 1840-41 in Rome studying the Old Masters and making frequent sketching trips. The following spring he joined Kensett and Rossiter in Paris, and spent the remainder of his sojourn abroad sketching in France and Germany.
Upon returning to the United States in 1843, Casilear resumed his career as an engraver. His skills and interests had expanded well beyond banknote engraving; eventually he was producing engravings of paintings for the American Art-Union's annual distribution to its subscribers. By 1854 Casilear's success had proved so remunerative that he was able to abandon engraving in favor of landscape painting. He established a painter's studio and made numerous sketching trips throughout New York State and New England. In 1857 he returned to Europe and spent two years working in England, France, and Switzerland.
Casilear returned to New York in 1859 and immediately took space in the Tenth Street Studio Building, which was his address for the remainder of his life. He quickly became a prominent member of the second generation of artists associated with the Hudson River School. In his Book of the Artists Henry T. Tuckerman wrote:
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The rectitude of his character and the refined accuracy of his original profession are exhibited in his pictures. They are finished with great care, and the subjects chosen with fastidious taste; the habit of dealing strictly with form, gives a curious correctness to the details of his work; there is nothing dashing, daring, or off-hand; all is correct, delicate, and indicative of sincere feeling for truth.
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Although Casilear's appearances in Academy annual exhibitions had been sporadic in his earlier years, when he was pursuing parallel careers as artist and commercial engraver, from 1851 on he hardly missed a year. Clearly well regarded by his colleague-artists, several of whom owned paintings by him, Casilear was elected to the Council by presumably differing constituencies of membership, serving in 1856-57, 1859-62, and 1872-73. The Academy's eulogy, entered into the minutes of October 9, 1893, noted:
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He was a capital draughtman [sic] and in certain tender silvery effects of light over quiet woodland and river scenes he was especially happy, his works being charged by a certain refinement of color and softness of atmospheric effect that won for him considerable distinction.
Those of us who have been associated with him for so many years will always remember his cheerful, manly ways, his bright conversations, and keen interest in art, so that our sense of loss can hardly be conveyed by a formal resolution.
