Shepherdstown was founded in 1822 and named for William Shepherd.
In 1951, Shepherdstown Elementary School, then known as Upper Allen Elementary School, was constructed just northwest of the community. In 1965, this building was renamed Upper Allen I with the addition of Upper Allen II directly next to it. Upper Allen II was later renamed Upper Allen Elementary School with Upper Allen I being called Shepherdstown Elementary School because of its proximity to Shepherdstown. Both schools underwent extensive renovation in the late 2010s and early 2020s. They are operated by the Mechanicsburg Area School District and are now located on a campus alongside Mechanicsburg Middle School and Trails and Trees Environmental Center.[2]
The Upper Allen Township Dog Park was developed along Old Hollow Road, next to Daybreak Church. It opened on June 30, 2018. The membership cost at the time of opening was $20/yr for residents and $50/yr for non-residents of Upper Allen Township.[3]
Plans for the construction of 37 townhomes on the south side of Shepherdstown were submitted to Upper Allen Township on February 1, 2011. The townhome development, named Terraces at Shepherdstown, began construction in 2021.[4]
In 2019, a mixed-use development named Shepherdstown Crossing (or Mills at Shepherdstown Crossing) was announced, to be located on the north end of Shepherdstown. The buildings were planned to have exteriors resembling early architecture of the American industrial revolution.[5]
The plan for the development originally called for two mixed-use apartment buildings, two fast food restaurants, and a three-story building. Plans to replace one fast food restaurant and the three-story building with a Chick-fil-A sparked debate among residents but were approved by Upper Allen Township commissioners on December 7, 2022.[6] The restaurant successfully opened at 6:30 AM on January 11, 2024.[7]
Shepherdstown Crossing also includes a forty-one-foot-high clock tower that was erected on December 13, 2022.[8]
A view from the hill in Shepherdstown, Pennsylvania, looking towards U.S. Route 15. The foreground shows a newly-constructed road to the Shepherdstown Crossing development. On the right hand side, the Terraces at Shepherdstown development, Upper Allen Dog Park and parking lot for Daybreak Church can be seen.
