Six days before the attack on Pearl Harbor, RY Sharpe purchased a small trucking company called Pennie Transportation that was going under. Mr Sharpe was no stranger to the trucking industry as he had been leasing his now fourteen truck fleet to Roadway Express. He renamed the business he just bought Pilot Freight Carriers and what began in 1941 was the start of what would later be one of the top 37 trucking companies in the nation.

Pilot began hauling general commodities between Winston-Salem, North Carolina and New York, New York. On December 22, 1943 the ICC approved the purchase by Pilot of certain operating rights and property of Joseph Meltzer Transfer & Express, Inc. ( from ICC Reports, Volume 38 page 803). R Y Sharpe had a brother with another Winston-Salem based carrier named Mitchell Motor Lines that in October  1946 merged with Pilot. By this time Pilot had terminals in   Winston-Salem, Baltimore, Philadelphia, New York City and Paterson, New Jersey. Mitchell contributed terminals in Charlotte, NC, Spartanburg and Batesburg, SC and Atlanta, Ga. By 1950 additional terminals were added in Greenville, SC and Hoboken, NJ. Growth in business meant expansion in the state of New York and by early 1953 there were six terminals in the state since about 20% of its yearly $6 million in revenues came from New York.

In 1957 Pilot bought 13 acres of land on Moonachie Avenue in Carlstadt, New Jersey. A 46 door terminal was built to combine facilities in Paterson, Hoboken and New Brunswick. The new location was Pilot’s largest terminal in the Northeast.

During the decade of the 1960’s Pilot Freight Carriers grew by making more acquisitions and building terminals. In 1959 the ICC granted temporary management control of Arlington Transportation, Inc. a New England based carrier with terminals in Cranston, Rhode Island, New York, NY, Boston, Mass and New Haven, Connecticut. Here is a list of points served by Arlington Transportation that was added to Pilot Freight Carriers territory: Connecticutt: Arlington, Branford, Bridgeport, Center Groton, Clinton, Coscob, Darien, Devon, East Haven, East Lynne, East River, Fairfield, Flanders Village, Greenwich, Guilford, Madison, Milford, New Haven, New London, Norton, Norwalk, Old Mystic, Old Saybrook, Stamford, Stratford, Westbrook, and Westport. Rhode Island- Abbotts Run, Albion, Anthony, Apponaig, Arkwright, Arnolds Mills, Ashton, Auburn, Barrington, Berkeley, Bridgton, Bristo;, Buttonwoods, Centerdale, Center Falls, Chepachnet, Clayville, Clyde, Conimicut, Coventry, Cowesett, Cranston, Crompton, Cumberland Hill, Daulsville, Diamond Hill, East Greenwich, East Providence, Esmond, Fiskeville, Forestdale, Foster, Georgiaville, Gendale, Grants Mills, Greenville, Greenwood, Greystone, Harmony, Harris, Harrisville, Hillsgrave, Hope, Hope Vally, Hopkinton, Hughesdale, Lakewood, Lincoln Park, Lunsdale, Lymansville, Manton, Mapleville, Mohegan, Mount Hope Point, Nasonville, , Natick, Nayaytt, Nousemeck

Another carrier taken over was Bison Fast Freight, with authority between Akron, Ohio and points in North and South Carolina, Georgia and Virginia. In the early 1960’s the largest terminal in the Pilot System was built in Kernersville, North Carolina, a small city near Winston-Salem that also had a huge breakbulk terminal for Roadway Express next door to the massive Pilot facility.

In February 1983 Pilot acquired Schuster Express inc of Colchester, Connecticut. After Schuster lost $1 million the year before they were faced with sharply higher federal taxes resulting in the need to sell out. With the combined company, Pilot would now have 82 terminals.

Heavy losses, increased competition from new lower cost carriers and the recession caused Pilot to be acquired in the early 1980’s to TNT, an Australian Shipping Company. By September 1987 heavy spending made TNT Pilot the biggest money loser on TNT’s list of 33 US holdings. But the spending thoroughly modernized the carrier after what some called years of neglect under previous ownership. TNT sold a controlling interest in Pilot to Taggart Group.

In December 1988 US Truck Lines bought Pilot and within months closed terminals, laid off employees and began selling assets. At one time the major terminal in Kernersville, NC had 550 employees and by March 1989 only 83 remained. Shortly after that, Pilot Freight Carriers shut down and ceased to exist.