The son of a local bank president, he graduated from the University of Vermont in 1845, studied at Harvard Law School for a year and in a local law office, and became an attorney in Burlington.
[1][2] From 1853 to 1854 Englesby served as Secretary of Civil and Military Affairs (chief assistant) to Governor John S.
[3] A Republican, Englesby served in several local offices, including city alderman, assessor, auditor and attorney.
In 1866 he was elected a trustee of the University of Vermont, a post he continued to hold until his death.
[4] Englesby was an active Mason, and was Grand Master of Vermont from 1862 to 1868.