That fall Ashley moved to Wilmington to study with Howard Pyle and occupied a studio at 1305 Franklin Street. He was present at Pyle's fiftieth birthday party in 1903, and spent that summer at Chadds Ford. After 1904 Ashley usually spent winters in Wilmington and summers in New Bedford, when he was not travelling elsewhere. In 1906 he and Peck began to share a studio at 1616 Rodney Street.
During much of 1908-09 Ashley was occupied with a business venture, buying mahogany furniture in Jamaica and selling it in Rhode Island. In 1913 he left Wilmington to settle in New Bedford, but he returned in the summer of 1915, staying at Stanley Arthurs's studio. The two artists travelled to California and then came back to Wilmington, where Ashley remained through the spring of 1916. At that time he moved his permanent Massachusetts resident to Fairhaven, near New Bedford. He often returned to Wilmington during the winter and may have rented his Franklin Street studio from Arthurs until as late as 1938. When Ashley married Sarah Rodman Scudder Clark in 1932, he began to renovate a farmhouse he had long owned in Westport, Massachusetts, and the couple moved there. They had two daughters, Phoebe and Jane.