Significant Dates:
April 28th, 1941: Inaugural run.
April 1958: Train numbers changed from 3 and 4 to 303 and 304.
February 1, 1968: NYC and PRR merge to form Penn Central.
May 1, 1971: First day of Amtrak operation.
July 1, 1972: Combined with the George Washington providing through coach service between Chicago and Washington DC.
March 6th, 1972: Chicago's Central Station is closed, train now calls Union Station home.

Introduction
Named after the famed Hoosier poet, the James Whitcomb Riley became the crack passenger train on the New York Central’s Big Four route from Cincinnati to Chicago. The Riley is noted for being one of the few New York Central passenger trains to not see a significant reduction in service and retain its name. In fact the Riley lasted into Penn Central and Amtrak while operating under the same name for over thirty-six years and on the same route for thirty-one years.

Something borrowed...
The Riley made its first run on April 28th, 1941 using a mix of hand-me-down equipment from the Mercury and four Budd built stainless steel coaches. Painted red and gray with a streamlined K-5b steam engine, the Riley was an impressive sight. The original consist included streamlined K-5b locomotives 4915 and 4917 from the Mercury, heavyweight baggage car 8551, Budd coaches 2560 and 2561, heavyweight diner 576, Budd coaches 2562 and 2563, and heavyweight observation car 52 (Doughty, 1999, p. 60).

Rainbow Consists
For the first two months of operation under Amtrak, the Riley remained relatively unchanged. On July 1, 1971 the Riley was combined with the former C&O George Washington finally providing through coach service between Chicago and Washington, DC.

Sources
Doughty, G. H. (1999). New York Central's Great Steel Fleet 1948-1967. Lynchburg, Virginia: TLC Publishing.

Doughty, G. H. (1997). New York Central's Lightweight Passenger Cars, Trains and Travel. Lynchburg, Virginia: TLC Publishing.