Simon Baker was one of Betsey and Charles Phelps's two indentured servants who arrived at Forty Acres around the age of 10 in 1766. Simon’s father signed a contract with Charles Phelps that required Simon to live and work at Forty Acres without pay for a term of 10 years and nine months. He could not go anywhere without Charles’ permission but was free to do what he wished after the 10-year period.

Based on documentation from Betsey Phelps, it seems Simon was an accident-prone child. In 1770, Betsey noted in her diary, “This night our little Boy Simon Baker Broke his toes at the saw mill.” Some months later, he cut his foot. Then he came down with quincy (tonsillitis). 

On April 20, 1777, Simon Baker (age 20-21), along with fellow hired hand Jonas Kelsey, enlisted in the Revolutionary War.