Chester was born with a natural talent for music, playing a number of instruments with ease, and was particularly well known around Bath as a fiddler for local dances. He became a '49er, sailing from Boston to Panama, probably on the brig "Randolph" on 6 Feb. 1849, arriving in Panama 6 Oct. 1849 according to newspaper reports. He then caught a steamship up the coast to San Francisco in the spring of 1849. After the first rush of excitement in California, many miners, including Chester, moved on to a gold strike in Colorado in 1858. There he met a sutler named Charles French Emerson from Oregon, Ogle Co., Illinois. When Fort Sumter was fired upon, Chester and Charles traveled east to Oregon. On 12 Aug. 1862 Emerson, age 46, enlisted in the 74th Infantry, Illinois Volunteers, Company G (Captain McCain's Company); while his friend Chester, age 38, enlisted in the same company the following day. Chester came down with rheumatic fever when his Company was left exposed to a cold, damp snow after they had won the Battle of Murfreesboro in Mar. 1863. Rather than invalid him out, as they did for the wounded Emerson, the Union Army transferred Chester to the Fifteenth Reserve Corps, and then to the Bugler Corps, where he served through the remainder of the war. He was mustered out at Cairo, Illinois in July 1865. Following the war, he married the much younger Ellen Elizabeth Norton, Emerson's sister-in-law, 26 Dec. 1865 in Oregon. Chester set up a tailoring business in Oregon, despite his growing infirmity from rheumatism, and they had three children while living there. In mid-April 1876, Chester closed his tailoring business, left his wife and children in Illinois, and travelled to the Black Hills gold fields. Ellen waited to give birth to their second son, Verner, then followed him with her four children, probably about 1878. They lived in Deadwood, Lawrence Co., South Dakota. Ellen died in there 16 Mar. 1880, possibly of erysipilas. Two aunts from Illinois and Vermont came west and fetched Ellen's four children back to Oregon, while Chester remained in the West. He visited the East twice in the following years, in 1886 and 1889, but soon returned to the mountains. On his last visit, he checked into the Illinois Old Soldiers' Home 14 Nov. 1889, but civilization did not agree with him. He left within weeks without communicating with anyone in his family. Chester died, probably of a rheumatic heart, on 16 Jan. 1890 near Boulder in Jefferson Co., Montana. It was only by chance, years later, that his children learned his fate.

Children:

Alvah William Eastman (1867-1952)
Harriet Belle Eastman McPherson (1869-1959)
Evelyn (Eva) Eastman (b. 1872)
Verner Eugene Eastman (1877-1953)