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.

The town also has a history of higher education. The Catholic based Calvert College began in 1851, although it was temporarily shut down when both teachers and students went off to fight during the war. The college was taken over by the Presbyterian Church and the name was changed in 1876 to New Windsor College. Blue Ridge College, which was located in neighboring Union Bridge, bought the college in 1912 and it opened as Church of the Brethren School until 1837. It was then sold to private corporations. It became the New Windsor Service Center in 1944. According to the town historian, it remains the oldest standing college building in Carroll County.

Today, New Windsor holds onto its history of the small town atmosphere, while welcoming new families as it moves into the 21st century, with the same charm and appeal as it did over two-hundred years ago.