As a boy, Cropsey suffered from his poor health, having to be absent from school periodically. During these episodes, he began to learn drawing by himself. His early subjects were mostly landscapes and architecture drawn on schoolbooks and notepads.
At first, Cropsey studied to be an architect, and by 20 years old, he opened his own office. He studied life drawing and watercolor under Edward Maury at the National Academy of Design, where he first exhibited in 1844. One year later, Cropsey was elected as an associate member of the Institution and began to work only on landscapes. The painter became a full member of the Academy in 1851.
He was a personal friend of the University of Michigan's president, Henry Tappan, who invited Cropsey to produce two paintings: a landscape of the University's campus along with the Detroit Observatory. One year later he went abroad and settled in London for seven years, although he would still send his paintings to the Royal Academy.
Returning to the United States, Cropsey initiated a new studio in New York, specializing in autumnal landscapes of the country's northeastern region, sometimes idealized and with vivid colors.
In 1866, Cropsey, alongside ten fellow artists, founded The American Watercolor Society, a non-profit group created to development of watercolor painting in the US.
Cropsey nurtured a keen interest in architecture, which accompanied him throughout his life and was an important influence in his paintings. This was very evident in his compositions which were precise and with harmonic arrangements. However, he was best known for his opulent use of color, especially in autumn landscape paintings, which delighted and surprised viewers with their dauntlessness and sparkling brilliance.
Cropsey married in 1847, with Maria Cooley, who he met in his several visits to Greenwood Lake. They had two children and were wed for 54 years.
Jasper Francis Cropsey died in June 1900; his wife Maria died six years later. Until their passing, they lived in their home called Ever Rest, which is today a museum in the artist's honor.