Rails were extended east from the the east into Elkhart Village in 1851.  The Daily Truth reported: "About four o'clock on a Friday afternoon early  in the month of October, 1851,  a wood-burning engine hauling a train of flat cars and a caboose, rolled over the wooden bridge across the Elkhart River and puffed along to the foot of Main Street which was then in the forest south of the village proper". The advent of the "Iron Horse" had been the topic of conversation for weeks around the village. Word spread abroad that the railroad would offer a free excursion to White Pigeon the next Sunday. The train for this event was a locomotive, a passenger coach, a boxcar and flat cars fitted with planks for seating. People came from miles around for the excursion. Calvin Dome, a boy of the village, was killed when a sudden stop threw him from the top of the box car and under the wheels.

The next year a railroad spur was built to Goshen. Railroad business was very profitable and competition was cut-throat. New railroad companies were incorporated by the legislature and established companies used the political process to block potential competitors.

Passenger traffic was brisk; 1912 passengers were transported by Nov. 30, 1888. The portion of the railroad between Goshen and Middlebury had numerous turns which lead to the nickname "Pumpkin Vine". A popular recreation was the excursion and many people visited friends and relatives using rail transport. Harrison won the Presidency in 1888 and an early excursion was a group of Republicans traveling from Goshen to Middlebury to help celebrate with a large bonfire and other entertainment.

A wreck occurred east of Shipshewana when an engine and three freight cars derailed. A track was quickly built around the wreck so service could be resumed. In the early days trains had to stop occasionally to remove ties and trees placed on the tracks by railroad opponents but these incidents did not cause any accidents.

State and local projects built highways in the 1920s and these created competition for railroads. By 1928 mail service on the Pumpkin Vine was terminated but the line had adequate business especially with industries in Middlebury.

The segment between Sturgis and Shipshewana was abandoned in August, 1960. The Pumpkin Vine Railroad became the property of Penn Central Corporation after the New York Central Railway and the Pennsylvania Railroad merged. Operations on the Pumpkinvine stopped in 1975 due to low profits and deteriorating facilities. Governor Bowen's Rail Task Force determined that the Pumpkin Vine would be profitable if it hauled 459 car loads of freight per year.