In the mid-18th century, residential and commercial “developer” was a term that was unheard of. However, Timothy Crosthwaite, a successful tavern (ordinary) keeper and landowner, living at the small crossroads community that would become Orange fit the definition applied generations later. He was born in 1721 in Philadelphia, Pennsylvania and emigrated with his father, William, to what would become Orange County in 1733. William Crosthwaite was granted a license to operate a tavern (presumably at this house) in 1741. After Crosthwaite’s father died, Timothy began selling much of his father’s land holdings to finance his life and business ventures in Orange County. Living on the property that once belonged to his father, Timothy Crosthwaite owned a tract in the area that soon became the permanent seat of the Orange County government and the location of the fledgling town of the same name.
Timothy Crosthwaite probably learned the tavern keeper trade from his father, and he operated his own tavern along the Swift Run Gap road since about 1743--likely known to many of the local residents and travelers through this section of the piedmont. Crosthwaite obviously had some political influence with county officials, because on November 24, 1749, the meeting place of the county court was moved from its original location near Raccoon Ford to Crosthwaite's tavern/house about midway between the present eastern and western boundaries of the county. A small settlement was already established at this location, but quickly a thriving village called Orange Court House began to grow up around the new county government buildings (courthouse and clerk’s office).
The county court continued to meet at Crosthwaite’s tavern until May 1752 when the new courthouse was completed. Crosthwaite’s home included other dependencies such as a stable, detached kitchen, garden, and spring. All of these were essential to maintain a prosperous tavern establishment. With county citizens drawn regularly to the courthouse, merchants established businesses around the courthouse.
In 1753, Crosthwaite conveyed a two acre tract to the county for the expressed purpose of building a courthouse for a sum of forty shillings. This “public lot” enclosed an area extending along the south side of Main Street from the Virginia National Bank corner to a point about one hundred feet beyond the railroad tracks and probably encompassed the areas bounded by Church and Chapman streets. Crosthwait was the caretaker of this courthouse which may have been located near the former police station on Chapman street. He supplied necessities such as beer, candles, and other items for the county justices and apparently was also the jailer. He did all this while also tending to his work as a tavern keeper.
Crosthwaite never married and died of unknown causes in June 1756, leaving his lands and possessions to his brothers and sisters. Crosthwaite’s insight and recognition of an opportunity to capitalize on the changing needs of the new county set the stage for the establishment of the town of Orange and the success that it has enjoyed during the previous generations. A similar spirit continues to be necessary for residents of Orange today.