The Old Stone Church at 304 E. Piccadilly Street is the oldest surviving church building in Winchester, completed in 1788 on the site of an earlier log structure that dated to 1736. The Presbyterian congregation that built it was among the earliest in the region, made up largely of Scots-Irish settlers who came down the Great Wagon Road from Pennsylvania in the mid-18th century. The building is a plain, sturdy piece of Federal-era construction that reflects the congregation's theological preference for simplicity over ornament.
During the Civil War the church was requisitioned by whichever army happened to hold Winchester at the time — it served as barracks, hospital, and stable depending on the season. The congregation continued to meet under occupation when possible. The building survived the war largely intact and has been preserved as a historic site. It is open to the public for tours on a limited schedule; the interior retains much of its 18th-century character. The churchyard contains early gravestones including some dating to the colonial period.