The James Whitcomb Riley was a passenger train that operated between Chicago, Illinois, and Cincinnati, Ohio, via Indianapolis, Indiana.

The James Whitcomb Riley was introduced by the New York Central on April 28, 1941, as a daytime, all-coach train between Chicago and Cincinnati by way of Indianapolis.

[2]: 91  The Riley was retained by the Penn Central (as trains 303 and 304)[3] after its formation from the merger of the New York Central and Pennsylvania Railroad, but in 1968 it petitioned the Interstate Commerce Commission (ICC) for permission to abandon the service, citing the loss of a mail contract and the Chesapeake & Ohio Railway's termination of through sleepers on the Chicago–Newport News route.

At the same time the route was extended from Washington to Boston, Massachusetts, and was assigned train numbers 50 eastbound and 51 westbound.

A broadcast by CBS's 60 Minutes in 1973 revealed that the Riley was limited to 10 miles per hour (16 km/h) in Indiana due to deteriorating Penn Central track.

[8] The Colonial began running over its former route between Newport News and Richmond, continuing northward to Washington and New York.