Painting
In New York, Cole sold three paintings to George W. Bruen, who subsequently financed a summer trip to the Hudson Valley where the artist produced landscapes featuring the Catskill Mountain House, the famous Kaaterskill Falls, the ruins of Fort Putnam, and two views of Cold Spring. Returning to New York, he displayed five landscapes in the window of William Colman's bookstore; according to the New York Evening Post the two views of Cold Spring were purchased by A. Seton, who lent them to the American Academy of the Fine Arts annual exhibition in 1826. This garnered Cole the attention of John Trumbull, Asher Brown Durand, and William Dunlap.
Among the paintings was a landscape called View of Fort Ticonderoga from Gelyna. Trumbull was especially impressed with the work of the young artist and sought him out, bought one of his paintings, and put him into contact with a number of his wealthy friends including Robert Gilmor Jr. of Baltimore and Daniel Wadsworth of Hartford, Connecticut, who became important patrons of the artist.
Eighty-nine of Cole's paintings were exhibited at the National Academy of Design between its founding in 1825 and Cole's death in 1848. Five of his works were engraved and published in The Token and Atlantic Souvenir annual gift book between 1826 and 1842. The historian David S. Lovejoy considers the best to be The Whirlwind (1837), which Lovejoy said "is unique in its boldness" compared to the predominantly serene landscapes of the period. Published in the 1830 volume, contemporary critic John Neal called Chocurua's Curse "beautifully contrived".
Cole was primarily a painter of landscapes, but he also painted allegorical works. The most famous of these are the five-part series, The Course of Empire, which depict the same landscape over generations—from a near state of nature to consummation of empire, and then decline and desolation—now in the collection of the New-York Historical Society and the four-part The Voyage of Life. There are two versions of the latter, the 1840 original at the Munson-Williams-Proctor Arts Institute in Utica, New York and the 1842 replicas with minor alterations at the National Gallery in Washington, D.C. Among Cole's other famous works are The Oxbow (1836), The Notch of the White Mountains, Daniel Boone at his cabin at the Great Osage Lake, and Lake with Dead Trees (1825) which is at the Allen Memorial Art Museum. He also painted The Garden of Eden (1828), with lavish detail of Adam and Eve living amid waterfalls, vivid plants, and deer. In 2014, friezes painted by Cole on the walls of his home, which had been decorated over, were discovered.
Cole influenced his peers in the art movement later termed the Hudson River School, especially Durand and Frederic Edwin Church. Church studied with Cole from 1844 to 1846, where he learned Cole's technique of sketching from nature and later developing an idealized, finished composition; Cole's influence is particularly notable in Church's early paintings. Cole spent the years 1829 to 1832 and 1841 to 1842 abroad, mainly in England and Italy.