Orlando was born in 1807 in New London or Montville, the son of Amos Bolles(1769-1811) and Elizabeth Mills (1773-1845). He married Ellen Fitch in Montville on January 18, 1835. They had at least four children: Harriet (Crandall) (1836-1926), Orrin (1843-1865 – he served with 1st CT Cavalry in Civil War, did he die during war?), Albert (1845-1939), and Anna (1849-1941). The 1850 census for Ledyard CT shows the family living there. Two years later, a census in Napa CA shows Orlando (age 42) living there as a “miner”. On October 13, 1892 Orlando registered as a voter in San Mateo CA. The registration form shows him age 85, born in CT, light complexion, blue eyes, brown hair, 5’ 6” (the crew list for EXILE shows him as 5’ 10”), occupation as carpenter, the end of the left finger cut off. A family headstone in Gales Ferry Cemetery lists the years of birth and death for Orlando (1807-1895), Ellen (1812-1856), and Orrin (1843-1865) and the year of Albert’s birth (1845). The headstone can be found at Find a Grave.
Orlando was master for one voyage on one ship with a home port of New London.
EXILE (AS1333) (schooner, 83 tons, 70’ long, built in Dorchester County, MD in 1830, license surrendered in 1861, later wrecked “abroad”). Sailed on July 17,1844 for Desolation Island, returned on January 8,1846. Leaned & Stoddard were the agents. AV04739.
Orlando was also master the schooner FRANCES (AS1393) (98 tons, built in Stonington in 1827, lost in Falklands February 15, 1842) for a voyage 1837-8. Her home port was Stonington. AV05102.
New London Crew Lists records Orlando serving on the crew of a ship named TALIMA in 1832, but no record could be found of a ship of that name. AOWV and Connecticut Ship Database record a schooner named TALMA (AS2471), built in Waterford CT in 1832, 65 tons, registered from 1830-1840. AOWV records only one voyage of TALMA, from 1834-1836. It is probable that the ship name in New London Crew List is misspelled and should be TALMA and that Orlando was on the crew for the 1832 voyage.
The New London Democrat (December 15, 1849) reports that the schooner EMPEROR under the command of Orlando sailed that day for San Francisco with a cargo of lumber, 3 house frames and other cargo.
Sources used: see sidebar and sources used in text.
George Shaw (Mystic Seaport Museum) December 2023