Born in Brandon, Vermont to Dexter and Emily (née Tilton) Whitcomb, George Dexter Whitcomb was the second of eight children. The family relocated to Franklin Mills, Ohio (now known as Kent, Ohio), where Dexter worked as a shoemaker and mechanic. Young Whitcomb attended public schools and later worked as a ticketing agent and telegraphist for the Panhandle Railroad to pay his tuition while at business college in Akron, Ohio. This was the beginning of a lifelong career and association with railroading.