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Chittenden was born in East Guilford, Connecticut and moved to Vermont in 1774, where he founded the town of Willston. During the American Revolution, Chittenden was a member of a committee empowered to negotiate with the Continental Congress to allow Vermont to join the Union. The Congress deferred the matter in order to not antagonize the states of New York and New Hampshire, which had competing claims against Vermont. Chittenden and fellow committee member Ira Allen then drew up the Vermont constitution establishing it as an independent republic -- the first republic in North America. Chittenden served as head of state of Vermont from 1778 to 1789 and from 1790 to 1791.
After Vermont entered the Union in 1791 as the 14th State, Chittenden became its first Governor, serving from 1791 until 1797. He died a few weeks after he left office.