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Ever since Shenandoah County was founded in 1772, the town of Woodstock served as the seat of local government. While the first court met in private homes, within a year a courthouse was in operation on this site. Ever since, this area has served as the legal, and often the cultural, social, and political, center of the county.

Large crowds were always present when court convened here on the third Monday of each month. Residents from throughout the county had to come to the courthouse to complete land transactions, to pay taxes, or to perform other legal transactions.

The presence of so many people was an opportunity most business owners could not pass up. Food vendors, horse traders, and money lenders flocked to town to provide services to visitors. Eventually these became permanent businesses, restaurants, and banks. Hotels also emerged to provide lodging. Theatres, music halls, taverns, pool halls, and bars also emerged in the general vicinity to provide entertainment.  Downtown in Woodstock developed within a single block of the courthouse.

Court Square, as this area became known, was home to more than legal and business activity. Since it was the largest structure in the area, the Courthouse became a community center. Churches, social organizations, volunteer groups, and even the local library met inside. Plays were performed in the structure. Militia units mustered here. The Woodstock Fire Department was organized on this site and moved only a few buildings away. School was taught on Lawyers Row and educational programs were held in several area buildings. The local political establishment also used the Courthouse as its base. It was a polling site, the location of rallies, and the background for speeches.

The system of Court Days and the activity that surrounded it changed in the 20^th century. Today the court system is in session throughout the year and residents can conduct legal transactions almost every day of the week. Large crowds only flock here for special occasions and most business is conducted outside of downtown. Yet the Courts, and the Courthouse, remain a symbol of the county and the town which built them.