From 1842 to 1844, he studied at Brown University, in Rhode Island, and left to New York City, to study under British artist John Rubens Smith, who taught him perspective, drawing, and anatomy. He also took anatomy and human figure classes at a Medical College as well as drawing at the National Academy of Design.
At 24, he was already a skilled painter, enough to have his artwork for the first time at the National Academy of Design. In 1851, he was elected as an Academy associate, and three later became an academician. Gifford then devoted himself only landscape painting and was regarded as one of the early Hudson River School’s finest artists.
Gifford traveled extensively throughout his life, like many Hudson River School artists, to find new scenics landscapes to paint and sketch. His subjects were mostly the northeast United States like upstate New York, New England, and New Jersey, although he traveled many times abroad.
His first trip to Europe was in 1855 and took two years, focusing on learning more about European art as well as making sketches and references for future paintings. During this period, he came to meet Albert Bierstadt and Worthington Whittredge; they became friends and extensive travel companions.
In 1858, Gifford traveled to Vermont along with his fellow painter and friend Jerome Thompson. Both artists submitted artworks to the annual National Academy of Design’s show in 1859. They were paintings depicting Mount Mansfield, the tallest peak in the state of Vermont.
Gifford spent most of the summer of 1867 painting along the New Jersey coast, especially at Long Beach and Sandy Hook. One of his most notable pictures from the said period was The Mouth od the Shrewsberry River, a striking composition that depicted a sequence of telegraph posts stretching through an aerial distance.