The first courts were held at the home of John Graham. According to local historians, court business was held in the tavern of Abraham Faw, which was located on Green street until a proper courthouse could be erected.An act by the General Assembly of 1793 authorized the construction of a courthouse and a jail. The courthouse was not ready for occupancy until 1799. The cost of the courthouse was $3,062.50.In 1806 the General Assembly allocated $1200.00 to build record rooms for the Clerk of Court and the Register of Wills. Even with the addition, the courthouse soon became too small for the county's growing needs. In 1834 the General Assembly provided that a new courthouse be built for $5,000.00. The new courthouse was ready to be occupied In 1841.
Thirty years later the General Assembly granted to the County Commissioners authority to issue bonds in the sum of $75,000.00 for enlarging and remodeling the courthouse and for building a new jail. The courthouse was enlarged, along with the Clerk of Court and Register of Wills offices. In addition, the appearance of the building, both inside and out, was beautified.
On January 5, 1893 the Courthouse caught fire and unfortunately the firefighters of Cumberland were unable to save the building, only the vaults of the Clerk of Court and Registers of wills survived.
Work began almost right away to build a new courthouse, which is the one in present day use. During this time the court held business in city hall. The Courthouse was constructed for a total cost of $97,000.00. The Courthouse is situated on the site of the old Fort Cumberland, overlooking the Potomac on one side and Wills Creek on the other. The Courthouse has changed little since its original construction. The building with its square steepled tower is the centerpiece of the Cumberland Historical District.