Born in Ireland, Richard Montgomery's military career started before he even finished Trinity College in Dublin. His father purchased an Ensign commission for him in the 17th Regiment of Foot. That got him to Halifax where he fought in the French and Indian War. Once Britain had control of Canada, Montgomery was sent briefly to the Caribbean and then back to New York to participate in Pontiac's War.
Returning to England, he became involved in Whig politics. He also got engaged. His fiance jilted him. When he wasn't promoted, he became disillusioned with the British army, sold his commission and decided to return to America and become a farmer.