Massie attended the College of William and Mary, starting at the age of 13 before withdrawing three years later to assist in the maintenance of his family's estate—the Windsor Forest Plantation in New Kent County—following the death of his father in 1751 and mother in 1759.
[2] When the American Revolution broke out, Massie would serve with the Elizabeth City District Battalion of Virginia minutemen in September 1775 before entering service with the Continental Army.
In March 1776 Massie was appointed as a captain in the 6th Virginia Regiment of the Continental Army, joining the unit in the defense of Perth Amboy, New Jersey, following the Battle of Long Island.
[3] Following the defense of Perth Amboy, the unit was ordered out back toward Newark, from where the regiment attached to the remainder of General Washington's army making their way through New Jersey on the retreat from British forces following the Battle of Long Island.
[3][4] Following action at Princeton and in the Battle of Brandywine, Massie was put under command of Colonel James Hendricks and moved toward duty at Middle Post, Matuchen.
General Washington replied, accepting his resignation on June 25, 1779: "I have received Your Letter of the 11th Instant—and I am extremely sorry to hear, that you have been so much afflicted with the Rheumatism.1 Your situation will not permit me to refuse your request to retire from the service; and I have only to regret the circumstance, which deprives the States of an Officer of your merit.
Around 1814, using slave labor, he ordered the construction of Pharsalia, the plantation home built on the Massie estate in Nelson County as a wedding gift to his son William along with 1,400 acres of land.