A Yale College graduate and Continental Army veteran of the American Revolution, Chipman became a prominent attorney and advocate for Vermont statehood.

[1][2] In January 1777, Chipman left Yale to volunteer for the Continental Army during the American Revolutionary War, and he received his diploma while he was serving.

[3] He took part in the December 1777 Battle of White Marsh, and went into winter quarters with his unit at Valley Forge, where they remained until June 1778.

[3] Chipman left the army to move to the Vermont Republic, where he attained admission to the bar and entered private practice in Tinmouth.

[1] Chipman also continued his military service as a member of Captain John Spafford's Company, a unit of the militia regiment commanded by Colonel Gideon Warren.

[1] On February 9, 1791, Chipman met with President George Washington to notify him officially of Vermont's decision to apply for admission to the Union as the 14th state.

[9] Following the admission of the State of Vermont to the Union, President George Washington nominated Chipman as the first judge of the United States District Court for the District of Vermont, a new seat authorized by 1 Stat. 197.

[1] Chipman was elected as a Federalist from Vermont to the United States Senate to fill the vacancy caused by the resignation of United States Senator Isaac Tichenor and served from October 17, 1797, until March 3, 1803.