Stewartstown is the seventh oldest borough in York County. In 1774 John Penn, son of William Penn granted James Savage 100 acres of land in Hopewell Township, and it is were Stewartstown now resides. There were settlers as early as 1750. The area that is southern York County was in dispute between Pennsylvania and Maryland even earlier and settlers entered under Maryland and Pennsylvania warrants in the 1720's. This dispute was resolved by the surveying of the Mason-Dixon Line in 1767.

The Susquehanna Indians used this area for hunting. The Indians practice of burning off underbrush to provide for better hunting caused the early settlers to give the region the name, "The Barrens".

Stewartstown's main street follows the path of a road, established in 1777, a route from York to Baltimore. Around 1812, several prosperous farmers set out to establish a community in south central Hopewell Township. The earliest buildings were several houses, a workshop (which produced furniture and spinning wheels) a store and a tavern. The workshop, owned by Anthony Stewart, became the meeting place.

Stewartstown village was known as Mead's town, after Benedict Meads, owner of the store and tavern. It then became known as Mechanicsburg, because of the number of carpenters, shoemakers, blacksmiths, wheelwrights and tinsmiths who lived in the community. In the early 1800's the town was large enough to have its own post office, because there was another Pennsylvania town called Mechanicsburg, postal officials gave the name "Guilford" to the community. Anthony Stewart was the first postmaster. Through efforts of Stewart and those of Judge Adam Ebaugh, the post office changed the towns post mark to Stewartstown on March 24, 1832. Pennsylvania authority incorporated Stewartstown into a borough in 1851. That was the year Stewartstown English and Classical Institute, known as the Stewartstown Academy, was chartered. Before the public high school was established, the Academy educated people who became distinguished ministers, doctors and lawyers. The addition of upper grades, to the public schools, around the turn of the century, led to declining enrollment, forcing the Academy to close in 1909. That site is now occupied by the funeral home.

Stewartstown had many businesses operating in its town such as: The Stewartstown Furniture Company, established in 1903, providing bedroom and dining room furniture, school and office equipment; The Stewartstown Lumber and Manufacturing Company, founded in 1885, now the Lumber Yard; The Stewartstown Manufacturing Company, owned by L. Grief and Bros. of Baltimore, established a branch of their men's suits and coats in 1933, that company employed around 400 people during peak operating seasons; The Stewartstown News, served the area from about 1890-1950; several cigar manufactures; a cannery; four blacksmith shops; Eller's surrey, buggy and sleigh establishment; a dairy; a creamery, hotels and several leather shops, where shoes and harnesses were made.

The Stewartstown Railroad in 1885 boosted manufacturing and commercial activity. Several times a day, trains carried loaded cars to New Freedom, where they were transferred to trains bound south to Baltimore, and north to York. Passengers regularly traveled on the Stewartstown Railroad for business as well as pleasure. Nature and a changing economy eventually brought freight traffic to a halt. As businesses closed, or moved away from Stewartstown, there was less freight order for the railroad. Then in 1972, the winds and rain in the wake of hurricane Agnes wiped out much of the connecting Pennsylvania Railroad rail bed, shutting down local operations. But the Stewartstown Railroad celebrated its centennial by resuming operations in 1985.

Stewartstown is experiencing new growth as a result of the search for "country living" by residents of the greater Baltimore area. New homes are being erected, old homes are being refurbished, and new business is coming to the town, like the American Vintage Bed and Breakfast for one.

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