In 1892, negotiations began to start the process of bringing a street railway to Oshawa. It took three years for the actual construction to begin, and on April 3, 1895, Robert McLaughlin of the world famous Carriage Works broke the sod to begin the project.
On May 15th, a contractor and a group of men took the materials and equipment waiting at the Grand Trunk Railway and began to tear up Simcoe St., laying the tracks, and stringing the appropriate wires. It took less than a month for it to be completed and on June 13th 1895 service was opened. Its inaugural trip started at the Grand Trunk Railway Station and ran as far as Mallory Row (Simcoe and Fairbanks Sts.) before it hit a rock and derailed. It was placed back on its tracks and continued north and went as far as the Simcoe St. Methodist Church. Later on it made it to the Four Corners. The press who were covering the story alluded to the fact that two of the cars were said to have met head on, messing up the appearance of the mayor. Despite this, free rides were given to all passengers on June 13.