Brooklyn Bridge, 1905, Marine Terminals, Poster, Large Photograph. New Haven/Bridgeport Terminal 20 with the Steamboat Chester Chapin.
The Chester W. Chapin, six generations removed from the family's pilgrim immigrant forebear, Deacon Samuel Chapin, was born in Ludlow, Massachusetts to Ephriam and Mary [Smith] Chapin, the youngest of seven children. He married Dorcas Chapin on June 1, 1825, and had four children, Abel Dexter, Margaret, Anna, and Chester W.
The family moved to Chicopee and in 1806 his father died, leaving Chester and his brothers to maintain the family and work their farm. He attended common schools and Westfield Academy, Westfield, Massachusetts. One of his first paying jobs was when local cotton mills were being built, when he earned $1.50 a day. He quickly went into business for himself, opening a store, and in 1822 was appointed town tax collector, for which he received $80.
Around 1826 he bought an interest in the stage line from Hartford, Connecticut to Brattleboro, Vermont, soon holding extensive mail and stage contracts. In 1831, when steamboats first began to run on the river between Hartford and Springfield, Massachusetts he bought an interest, soon became sole proprietor, and for about 15 years controlled all the passenger traffic on that route. He also became a large or principal owner of the steamship lines between New York City, Hartford and New Haven, Connecticut. He later extended his interests into railroads and banking, becoming founder, principal or president of many companies, including the Western Railroad, the Agawam (National) Bank, and the Connecticut River Railroad. He was one of the earliest advocates of a bridge over the Hudson River at Albany, New York. He served as member of the Massachusetts Constitutional Convention of 1853, president and director of the Western Railroad Corporation from 1854 to 1867, president of the Boston and Albany Railroad from 1868 to 1878, and a director until 1880.