In 1941, Roseway was purchased by the Boston Pilot's Association to serve as a pilot boat for Boston Harbor. Following the attack on Pearl Harbor later that year, mines and anti-submarine netting were installed to protect the Port of Boston, and all lighted navigational aids were extinguished. Roseway was fitted with a .50 caliber machine gun and continued her piloting duties in this challenging environment, for which service her pilots were awarded a bronze plaque from the Coast Guard at the end of the war.
Roseway continued to serve as a pilot vessel until the early 1970s, at which point she and San Francisco's Zodiac were the only pilot schooners still in service in the United States. She was then sold and converted into a passenger vessel for the tourist trade. Roseway changed hands several times in the ensuing decades, operating primarily out of Camden, Maine and the US Virgin Islands. In 1997, she was listed as a National Historic Landmark. Roseway, at that time, retained between eighty and ninety percent of her original hull fabric and was badly in need of repairs. She remained docked in Rockland, Maine until she was repossessed by the First National Bank of Damariscotta, which in 2002 donated the vessel to the newly founded World Ocean School.
Following two years of restoration in Boothbay Harbor, Roseway again set sail in 2005. She currently serves as the platform for the World Ocean School, which offers various educational programs in St. Croix and the northeastern United States.