Chester William Chapin was born on December 16, 1798 at Ludlow, Massachusetts, United States, the youngest of the seven children of Ephraim and Mary (Smith) Chapin. He was descended from Deacon Samuel Chapin who settled in Springfield in 1642.
Chapin received formal education, which was limited to a few winters at the district school and a season at Westfield Academy. This meager schooling was in part due to his father’s early death which necessitated a boyhood of arduous toil.
As a young man, Chapin was employed with a yoke of oxen in constructing the foundations of the Dwight mill, the first of Chicopee's manufacturing concerns, and for a short time after reaching his majority he tended bar for his brother Erastus, a Springfield inn-keeper. Returning to Chicopee, he conducted a country store, took contracts for building construction. His subsequent career was tied up closely with the development of transportation in the Connecticut Valley.
His first connection with the transportation business was as driver of his brother’s ox-team which carried merchandise from the river wharves to the Springfield stores. The next step was the purchase from Horatio Sargeant, who owned most of the Springfield stages, of a part interest in the Northampton line, and the two men soon became partners in the Brattleboro and Hartford line.
No sooner had the practicability of steamboat navigation on the Connecticut been demonstrated than Chapin and Sargeant entered aggressively into the building and operation of steamboats until they became not only the chief concern operating river steamboats, but enjoyed for a long time a practical monopoly of the passenger business between Springfield and Hartford. Chapin’s steamboat interests eventually included the ownership of boats running from Hartford and New Haven to New York. With the coming of railroads Chapin sold his steamboats operating north of Hartford and entered enthusiastically into the development of steam railroads.
He was a prime mover in getting the New York & New Haven Railroad to extend to Springfield, and soon became a large stockholder in the Western Railroad (the present Boston & Albany) and in the Connecticut River Railroad. He was president of the latter (1850 - 1834) when he was called to head the Boston & Albany. His presidency, which extended to 1877, was a time of prosperity and wise development and included the period of consolidation with the Boston & Worcester which insured through western connection with Boston. Notwithstanding the fact that the Massachusetts legislature censured him because of the leasing by the Boston & Albany of the Ware River Railroad, an enterprise in which he was personally interested, the Springfield, Republican said that “He had no sympathy with the modern gambling school which waters stocks and preys upon corporations without regard to the public interest”.
Chapin was also a vicepresident of the Hampden Savings Bank as well as a director of the Springfield Fire & Marine Insurance Company and the Massasoit Insurance Company. Moreover he was a large landowner and was interested in various manufacturing establishments.
A life-long Democrat in a Republican district, Chapin had the confidence of his fellow citizens sufficiently to be elected to several town and city offices, to the state legislature in 1844, to the Massachusetts constitutional convention of 1853, and on a reform wave to the Forty-fourth Congress in 1874. He was one of the seceders at the Democratic convention at Baltimore in 1860 and was later a Breckenridge and Lane elector. He became a war Democrat and largely paid for the uniforms of the city guard when that body joined the both Regiment.
Chapin became one of the wealthiest residents of Springfield and railroad and steamship magnate. He was known as the founder of the steamship line, several railroads and a number of banks, including Chapin Bank and the Agawam Bank. He also participated prominently in the building of the first street car line in Springfield.
In appearance Chapin was described as a man of “commanding presence with a firm impassive face whereon the stubby grey moustache covered the lines of a strong mouth”.
Chapin married Dorcas Chapin, daughter of Colonel Abel and Dorcas Chapin. They had four children.
