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Underhill was chartered in 1761 by Colonial Governor Benning Wentworth and named for his friend, Sir Henry Underhill. The town was settled in the early 18th century by colonists from Connecticut and Massachusetts, who were attracted to the area's fertile farmland. In 1778 during the Revolutionary War, General John Burgoyne led British forces through Underhill on their way to defeat at Saratoga; a monument marking this event stands near Route 15A. In 1851 a railroad line connecting Montpelier with Burlington opened; it passed through Underhill village (then known as "Underbill"), where there was an important junction with lines running eastward toward Stowe and westward toward Rutland.