As a teenager, Silloway was apprenticed to a housewright and as a clerk in an East India merchant store.
In 1862 Silloway started a second career as a Universalist minister in New Hampshire, Boston, and Brighton, Massachusetts.
He left the ministry in 1867 when his architectural work increased.
By the time he died in 1910 Silloway was credited for designing more church buildings than any other individual in America.
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