Isaac Atlee laid out New Windsor in 1796. It sat astride the Old Monocacy wagon road that stretched from Winchester, VA to Philadelphia. Atlee hoped to capitalize on all of the traffic by opening an inn and tavern on the corner of what is today Main and High Streets, and by leasing lots to shopkeepers and tradesmen. His design for a commercial center consisted of 28 lots along Main Street, named Bath Street on the original plat.
The town of New Windsor grew slowly with original lots being leased through 1812. A major attraction was a sulphur spring which Atlee owned at the foot of Main Street. The waters were thought to have medicinal benefits and helped to draw guests to his inn. For a time the town enjoyed the nickname, "Sulphur Springs."
The stage coach and wagon roads which cut past the inn, connected the area with Baltimore, Gettysburg, New York and Philadelphia. New Windsor found itself the crossroads of much commercial activity and became a leading community for business.
This easy accessibility also brought armies of the North and South to the town during the Civil War. In the summer of 1863, five thousand Union cavalry rode through the streets on their way to bolster the Northern forces at Gettysburg. Two of their dead were buried in the Presbyterian Church cemetery. The next summer, 500 Confederate cavalry swooped into the village and looted the stores of food and clothing.
The coming of the railroad in 1862 strengthened New Windsor's commercial standing. New stores and hotels sprang up ad the rails also gave area farmers easy access to eastern markets. This new-found affluence was later reflected in the elegant homes crowning upper Church Street proudly dubbed "Quality Hill."
The social hubs of the town were its churches, fraternal organizations and Atlee's old inn, then owned by the Dielman family. The inn played host to countless visitors from the big cities seeking relief from the summer heat. Another center of activity was the college on the hill overlooking the town. Through its history, the school operated as Calvert College, New Windsor College, and Blue Ridge College respectively as its church affiliations changed. Today it is the Brethren Service Center operated by the Church of the Brethren providing programs in refugee resettlement, disaster response, conference facilities, also providing warehouse and gift shop space to SERRV International Handicrafts.
By the early 20th century, modern transportation and technological advances began to significantly change the make-up of the regional small towns. Today New Windsor meets its challenges with all the charm and friendliness of yesteryear, making it one of the beauties in Carroll County's pageant of small towns.