Dr. William Seward Webb (1851-1926), president of the Rutland Railroad and the Wagner Palace Car Company, lived part of the year in Shelburne and commuted to New York City in his private car, the Ellesmere, which was similar to the Grand Isle. The Grand Isle was originally presented to and used by Vermont's governors. J. Watson Webb, Jr. (1916-2000), Electra Webb's son and Dr. Webb's grandson, acquired the Grand Isle and supervised its renovation to commemorate his family's role in the railroad industry. Its mahogany-paneled parlor, elegant dining room, and plush staterooms are typical of the private luxury cars that became important symbols of corporate and personal status in the late 19th century.