Jasper Cropsey was born on his father's farm in Rossville, Staten Island on February 18, 1823. As a young boy, Cropsey had recurring periods of poor health. During these periods, while absent from school, Cropsey taught himself to draw. His early drawings were architectural sketches and landscapes drawn on notepads and in the margins of his schoolbooks.

His artistic skills improved rapidly as Jasper mimicked whatever paintings, drawings, and architectural renderings he could find. At the age of fourteen, Cropsey entered an architectural model in a contest and won a diploma from the 1837 Mechanics Institute of New York fair. Soon Jasper Cropsey began a five-year apprenticeship for Joseph Trench, architect. Trench realized young Jasper's artistic ability and provided him with studio space and art supplies in order to develop his artistic skills. Jasper took advantage of Trench's encouragement and sketched and painted whenever he could. Cropsey mostly painted landscapes, copied from engravings of Claude Lorrain and other landscape artists.