Stephen was born on November 9, 1826 in Waterford CT, son of John Raymond Bolles and Julia Ann (Hewlit) Bolles. According to a crew list, he was 5’ 6” with dark hair and dark skin. He married Anna M. Avery on August 31, 1856 in Waterford. She was born on December 8, 1836 in Homer NY and was a member of the eighth generation of the Groton Avery Clan of which there is an extensive written family history. They had no children but they adopted Josephine Haley, daughter of Nathan Haley and granddaughter of Hannah Avery, thus joining her adoptive mother as a member of the Groton Avery Clan. During the Civil War, Stephen was an ensign in the Navy, serving on the WEEHAWKEN and AGAWAM. The census reports for 1850 (Waterford) and 1870 (New London) show Stephen’s occupation as “mariner”; the reports for New London for 1880 and 1900 show his occupation as “retail fish market” and “fish dealer” respectively. The 1900 census shows living in the household with Stephen, Anna, and Josephine a grandson, Stephen B. Bolles, born August 24, 1892. Stephen (Sr.) died on November 17, 1903, Anna died in 1921, both in New London. They and Josephine are buried at Cedar Grove Cemetery in New London (sec. 17). The gravestone can be found at Find a Grave.
Stephen was master for one voyage on each of two ships with a home port of New London.
IRIS (AS1659): (bark, 245 tons, built in Kittery ME in 1823, sold to Boston in 1859). Sailed on October 28,1856 for the Pacific, returned on May 2,1859.Frink & Prentis were her agents.
PERRY (AS2170): (bark, 150 tons, built in Norfolk VA in 1843, wrecked in a hurricane in Bermuda on August 29, 1880, Starbuck shows her “Formerly of the United States Navy”). Sailed on May 29,1867 for the Atlantic, returned on July 21,1870. Williams & Barns were her agents. AV11413
New London Crew Lists records Stephen serving as master of a ship named RELEASE in 1866, but no record could be found of a ship of that name. He served on the crew of CANDACE (AS1029) on her 1845-1847 voyage.
Sources used: see sidebar and sources used in text.
George Shaw (Mystic Seaport Museum) November 2023