Sylvester May was the eldest son of Hezekiah May and Sarah (Sally) Hayes. Born April 1808, Sylvester moved from Stanstead Township to Barnston Township, in 1832 where he purchased a farm near Lake Lyster. He was first married to Almeda Marsh (1813-1842) and together they had at least two children: Amanda Melvina (1837-1900) and Sophia (1841-1842). After the death of Almeda, Sylvester married Eunice Bean (1813-1852) on the 6 June 1843. Together they had at least five children: Darius (1843-1913), Lyman Albert (ca. 1844-1923), Wilber (1846-1852), Caroline S. (b. 1848) and an unknown child (born and died in 1845). Lastly, he married Sarah Wadleigh (1812-1902) on 11 October 1853 and they had at least one child: Ida (1855-1925). While an obituary for Sylvester states that he had ten children, it appears that there is only record of eight.
Sylvester May died 5 September 1901 and is buried at the Lakeview Cemetery in Baldwin's Mills.