He was born in Springfield, Massachusetts in 1835, the son of Eli Stephenson and Chloe Chapin. He was educated at the Grantham Academy in St. Catharines, Ontario. Stephenson worked as a printer in St. Catharines and came to Chatham around 1850. With Charles Stuart, he took over the ownership of the Western Planet, later the Chatham Planet, which he managed until 1878. He was elected to the town council in 1861, served as reeve in 1863 and mayor in 1865-1866. He served as government whip from 1878 to 1882. After he retired from federal politics, he served as customs collector at Chatham until his death in 1901. Stephenson was a member of the Freemasons.