Gamaliel Painter was born on May 22, 1743 in New Haven, Connecticut, United States. He was the third son and the youngest of the six children of Shubael and Elizabeth (Dunbar) Painter. He was a descendant of Thomas Painter who was living in Massachusetts in 1637 and later moved to Rhode Island.
Gamaliel Painter received only a common-school education, perhaps at Salisbury, Connecticut.
Until the outbreak of the Revolution, Gamaliel Painter was busy with the usual duties of the backwoodsman, clearing and planting his land, making surveys, opening roads, and, like most early settlers in western Vermont, resisting New York claimants to his lands. With the outbreak of hostilities he promptly joined the army, apparently serving with the expedition to Canada in 1775. The next year he became a lieutenant in Warner's Additional Continental Regiment. Later, he held a captain's commission in Baldwin's Artillery Artificer Regiment. He retired from the service in April 1782. Meanwhile, he had represented Middlebury at the two conventions at Dorset, January 16 and September 25, 1776, and in the Windsor Convention (1777) which formed the state constitution he sat for Cornwall. When, however, British forces that year occupied much of the western part of the state, he withdrew from Vermont, returning with his family in 1784.
In 1787, after buying part of the site of the future village of Middlebury, he moved there and engaged actively in laying out village streets and selling lots. He erected a gristmill to attract settlers and engaged in various enterprises to promote the prosperity of the settlement which he was fathering. A simple, unassuming man, slow and halting in speech, and without any claims to consideration on the score of culture or education, he nevertheless won a position of authority in the new community. His sturdy physique and native mechanical sense fitted him admirably for the manifold tasks of the frontier. Sound judgment and shrewd business acumen, combined with energy and initiative, soon gave him a competence, which in the next thirty years grew into a considerable fortune for that region. Having won the respect of his neighbors he renewed his political activity.
Though without legal training, he served as assistant judge of Addison County from 1785 to 1786 and from 1787 to 1795. In 1786 he was elected from Middlebury for the first of fourteen terms in the lower house of the state legislature, a service which continued with some interruptions until 1810. Thereafter, he was twice (1813 and 1814) a member of the council which shared the executive powers with the governor. Conscious of the handicaps of a deficient education, he was an eager promoter of public instruction. He was one of the five original trustees of the Addison County grammar school founded at Middlebury in 1797, and when, in 1800, Middlebury College was added to this institution, Painter was one of its fellows. This administrative position he held until his death. He died on May 21, 1819. He provided that after the death of his third wife his estate should go to the college which he had helped to found and the building of which he had helped to erect.
Throughout his life Gamaliel Painter was a firm Federalist.
On August 20, 1767, Gamaliel Painter married Abigail Chipman. With her brother, John, he purchased land in the township of Middlebury, Vermont, possibly from his own brother, Elisha, who was one of the original grantees in 1761. After preliminary explorations he took his wife and two sons to Vermont in 1773. His first wife having died in 1790. In 1795 he married Victoria Ball of Salisbury, Connecticut, by whom he had one daughter. Some time after 1806 he married for a third time, Mrs. Ursula Bull, daughter of Isaac Bull and widow of William Bull, of Litchfield, Connecticut. His three children died.
