The Orlando & Winter Park Railway

The Orlando & Winter Park Railway was built in 1889 to connect Winter Park, FL to Orlando, as the name would suggest. Initially resembling more of an interurban than a traditional line, it ran on streets for part of its operation. Unlike similar lines, it never became electrified, relying on steam power until dieselization occurred. (Right of way)

It was nicknamed "The Dinky", which was a common nickname for branch line or small passenger train services in the early 20th century. 

A shot of the O&WP steam engine and some rolling stock. (Goldenrod Historical Society)

"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 line 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." (Goldenrod Historical Society)

"The Dinky Line's rails in the woods." This is a 1907 post card from Lake Virginia, Orlando, FL. (Winter Park Public Library)


The earliest iteration of service along this route, and the area itself, could hardly be more different than modern day railroading. Speeds averaged just over six miles per hour, and as much of the rails were built directly into sand, derailments were quite common. At the time, "much of the route between Orlando and Winter Park was wooded and undeveloped. If service was not interrupted by derailment, stray cattle blocked the tracks and delayed service until the conductor stopped to shoo the cows away." (Steve Herring, Bungalower)


While many similar short line railroads would go bankrupt, the O&WP was given a second life. Early in the 20th century, the line was acquired by the Seaboard Air Line Railroad, who extended it an additional nine miles northeasterly to Oveido, FL. A branch to Orlando's Municipal Airport was also built at this time.
Orlando & Winter Park Railway Station, late 1800's. (Bungalower)

Even under the tutelage of the Seaboard, the street running segments were not relocated. Despite running along the streets and ending passenger service, the continued to be operated by the SAL until 1969, although with only one train a day during the 1960's.

Part of the former right of way has been incorporated into the Orlando Urban Trail. The spur to the airport right of way has become the Cady Way Trail.

Thanks as always for reading!

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