Skip to main content
Winter Park Library Archive

The Dinky Railroad

The Winter Park Company granted rights of way for a railroad to J. Harry Abbott in 1887, but due to inefficient contractors and an epidemic of yellow fever, the first run was delayed significantly.The Orlando-Winter Park Railroad formally opened on the morning of January 2, 1889, when the train arrived from Orlando. The return trip was scenic and peaceful, except for the fact that by the end of the journey, two coaches had run off the track.  No one was injured, and these "happenstances" were taken in good humor. Francis B. Knowles was soon after elected president of the Orlando-Winter Park Railroad Company, though he died in May 1890.

The trip between Orlando and Winter Park measured six miles and took about a half-hour.  In March 1889, tracks were laid through the Rollins College campus. Students from Orlando began taking the train to school; previously, they had had to make the trip on horseback. There was but a small platform on campus, but at the foot of Ollie Avenue, a few blocks away, stood an impressive Victorian-style depot which is now the site of Dinky Dock.  Over time, the Dinky Line, as it was named by Rollins students, became infamous for its noisy rumblings, slow pace, frequent tardiness, black belches of smoke, and, because of the sandy terrain, its "remarkable ability to leave the tracks," according to a 1967 edition of the Rollins Sandspur.  The two engines were known as the "Tea Pot" and the "Coffee Pot," and the train itself was the "Little Wiggle."  Pranksters enjoyed pouring oil or soap on the tracks, prompting profanities from the crew, who would then have to shovel sand onto the tracks to get the train moving.  In its heyday, the Dinky Line made as many as eight round trips a day for a 15-cent fare.  It was even expanded to reach Oviedo in 1891.  But over the years, as automobiles became more prevalent, the railway faded into obscurity, discontinuing passenger service, and by the 1960's was running only once a day.  In 1969, the final removal of the tracks was completed.

This article was written by former archivist, Barbara White, MLIS.