Penn Township, Cumberland County is located in the southwestern section of the county. The township was formed officially on October 23, 1860 by partitioning off the western half of Dickinson Township. In 1872, the southern portion of Penn Township was partitioned to form Cooke Township. The township’s boundaries have remained unchanged since that time. To the south the boundary is Cooke Township, to the north it is West Pennsboro Township with the boundary formed by U.S. Rt. 11 (the Joseph Ritner Highway), to the east the township boundary is formed just east of Huntsdale with Dickinson Township and to the west the boundary is formed by South Newton Township just east of Jacksonville.
Earliest settlement in the area began in the eighteenth century when the area was part of West Pennsboro Township. Dickinson Township was created in 1787 and the area was under that jurisdiction until 1860.
Originally, township business was conducted in Centerville, the largest of several villages in the township. Business was conducted from one of the taverns in the village, the Brick Tavern at Sporting Hill run at that time by Jacob Redsecker. In the mid-20th century, township business was moved to a new township facility in South Fairview (Brushtown).
The two main geographic features of the township are Yellow Breeches Creek and the initial slopes of South Mountain. Yellow Breeches Creek begins its flow to the Susquehanna on the western boundary of the township at Three Springs. The soil is partially sand based, often referred to in the historic records as Pine Land. The other main soil type is limestone based and is prized for its rich agricultural opportunities.
The main early transportation routes through the township are the Walnut Bottom Road and U.S. Rt. 11, historically known as the Great Road from Pittsburgh to Philadelphia and later the Chambersburg Harrisburg Turnpike, a toll road for many years. Because of these two roads, the township played unwitting host to the Confederate Invasion of the Valley in 1863 prior to the Battle of Gettysburg.
In the 1870s, another transportation facility was added, the Harrisburg and Potomac Railroad, later the Reading Railroad, then Conrail, and in 2014 the Norfolk Southern Railroad. The final addition to major transportation routes was added in the 1960s, Interstate 81, part of the national grid of limited access highways constructed throughout the country.
The major business of the township has been and remains agriculture. The fairly recent influx of old order Mennonite families in the area has helped stabilize the agricultural aspect of the township. A number of smaller business ventures have exited in the township throughout its history. More recently, the warehouse industry has made its presence felt with the construction of two large warehouse complexes near the I-81 Newville exit. Pennsy Supply has also established a large quarry in the northwestern corner of the township.
One of the distinguishing features of the township is the many villages. In addition to Centerville and South Fairview, already mentioned, others include Huntsdale, an early industrial milling center, Hays Grove (Sidetown), Cobblersville, Hockersville, and Cummingstown, site of the oldest church in the township, the Dickinson Presbyterian Church.