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Around 1830, Townsend Winters of Steuben County, New York, purchased 400 acres of land for $2,000.00, about twelve miles from York and seven miles from Stewartstown, on which the scattered Borough of Winterstown is now built.

This wooded land was laid out into lots, and a dirt road was constructed. After the timber was cut, several homes were erected along the road. Winters planted a large apple orchard and the village was named "Apple Grove". Land was sold in large lots. Winters began to build a house which, before its completion, was purchased by Daniel Brenneman, a blacksmith, who erected a blacksmith shop on the property. (This property was later owned by David Herbst and after Mr. Herbst it was owned by Ralph Rineholt.) Winters then constructed another house where he lived, and where his wife died. She is buried in St. Paul's Cemetery. (This home was occupied by Henry Landis for over fifty years and and was then purchased by Marcellus Baughman.)

After his wife's death in 1875, Winters moved to Galesburg, Illinois. However, before leaving for the west, in order to perpetuate his own name, he changed the name of "Apple Grove" to "Winterstown" which was retained when a charter for incorporation was obtained.

Winterstown became a borough when it was surveyed out of Hopewell Township (now North Hopewell Township) by William Norris. The borough's charter was granted on January 2, 1871.

Winterstown is one of the largest municipalities in square miles in York County. Population-wise it is not so large. According to the 1880 Census, 190 people lived in the borough; the 1900 Census recorded 217; and the 1970 Census counted 422 residents, and the 2000 Census counted 546 residents.

Farming was and still is a principal occupation of community residents. Some of the farms have been owned by the same families for several generations. The gently rolling land is very productive. Traveling south from Red Lion on Route 24 through Winterstown, the traveler views a picturesque country town.

Winterstown Volunteer Fire Company was organized in February, 1954. In 1958, the Fire House was built on ground donated by Curtis Hildebrand and Mrs. Addie Herbst. Labor and some materials were donated. In 1966, a new John Bean Fire Engine was purchased for over $16,000.00. The Company has had a number of presidents in its history, including: Ralph Rineholt, Lester Hess, Morgan Overmiller, and Curtis Zeigler, Sr. A Ladies Auxiliary to the Company was formed in 1956.

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