First of the New Hampshire Grants, Bennington was chartered on January 3, 1749, by Colonial Governor Benning Wentworth and named in his honor. It was granted to William Williams and 61 others, mostly from Portsmouth, New Hampshire, making the town the oldest to be chartered in Vermont and outside of what is now New Hampshire, though Brattleboro had been settled earlier as a fort. The town was first settled in 1761 by four families from Hardwick and two from Amherst, Massachusetts. They were led by Capt. Samuel Robinson, who camped in the river valley on his return from the French and Indian War.
Prior to the arrival of colonialists, the land belonged to the Western Abenaki of the Wabanaki Confederacy. These peoples were indigenous to Ndakinna—also known as Vermont, Maine, Massachusetts, New Hampshire, New York and Quebec.