The Town of New Windsor was laid out and surveyed in 1797 by Isaac Atlee, who hoped to capitalize on traffic coming from Winchester, Va. to Philadelphia on the Old Monocacy Wagon Trail. He opened an inn and tavern on the corner of Main and High Streets, which are now the town's main thoroughfare MD Rt. 31. The commercial center consisted of 28 lots along Main Street which was called Bath Street on the original plat. The town thrived during the 1820's and became the leading community for business. A military road intended to connect Buffalo, NY provided the town with considerable commercial activity.