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Stewartstown is a borough in southern York County, near the Maryland line, and is part of the York–Hanover metropolitan area.

Settlers were in the Stewartstown area as early as 1750, when the land was claimed by both Maryland and Pennsylvania; the boundary dispute was settled by the surveying of the Mason–Dixon line in 1767.

Around 1812 a group of farmers set out to establish a town in south-central Hopewell Township on land purchased by Anthony Stewart, whose furniture and wheel workshop became the village's main meeting place.

The village was first called Meadstown and then Mechanicsburg for its many tradesmen, and its Main Street still follows the old York-to-Baltimore road that was well established by 1777.

Anthony Stewart became the town's first postmaster in 1828, and through his efforts the Post Office Department changed the town's postmark to 'Stewartstown' on March 24, 1832.

Stewartstown was incorporated in 1851 under the name Mechanicsburg and was reincorporated as Stewartstown on February 24, 1853.

The Stewartstown Railroad has connected the borough with the Northern Central Railroad at New Freedom since 1885, and the Stewartstown Railroad, its station, and its engine house are all listed on the National Register of Historic Places.

Stewartstown sits in one of York County's richest fruit-growing areas, and in the summers of 1944 and 1945 a prisoner-of-war camp in the borough housed German prisoners who worked as farm laborers.

The 2020 census counted roughly 2,130 residents in Stewartstown, up from 1,752 in 2000, when the borough had 678 households.

Stewartstown is served by the South Eastern School District.