The history of Ashford began in 1710 when it was settled and then, in 1714, it was incorporated as a town. Due to its location between Boston and Hartford, the town became an important center for travel and commerce. In the 1800s, it held mills, tanneries and small stores. Later, in 1840, the town was considered a transportation hub. Also, Ashford is known for its notables and what they did for the nation. One of them is Edward W. Whitaker, who was an officer in the Union Army. He made a significant impact by delivering dispatches to Major General George Meade, riding through the enemy lines during the Civil War. In 1864 he received the Medal of Honor.