In 1924, William T. Cowan established W.T. Cowan, Inc., which consisted of a single truck that he owned and operated. Mr. Cowan hauled Hendler's ice cream from the creamery in Baltimore City to a commissary in D.C. Cowan was a savvy entrepreneur, who expanded his “Fast Freight” business to provide LTL service throughout the Middle Atlantic States. 

Notably, W.T. Cowan received the distinguished honor of selection as the transportation company for the Iwo Jima Memorial statue.  In 1954, seven W.T. Cowan trucks conveyed the 100 ton statue from the Bedi-Rassy Foundry in Brooklyn, New York to Arlington, Virginia.  The drivers included Al Jackson, Dick Altersitz, George Austen, and Bud Reilly.  

In June 1963, the W.T. Cowan fleet was also responsible for transporting cathedral bells for the Washington National Cathedral Carillon.  The ten English ringing bells, which were cast by the Whitechapel Bell Foundry of London, ranged in weight from 608 to 3,588 pounds.  

In 1979, Cowan opened Key Warehouse Services, a warehouse and distribution company, which maximized the advantage of having a small fleet.  As deregulation occurred within the trucking industry, the company was transformed into an irregular route truckload carrier. 

Joseph W. Cowan, the son of W.T. Cowan, opened Cowan Systems, LLC. as a new operating entity in 1994. Cowan Systems expanded the company focus to include the services of a specialized truckload carrier, including fleet replacement and dedicated fleet services.  

Today, Cowan’s state-of-the-art fleet has grown to nearly 2,000 power units and 5,000 trailers.