Ontario South Land Railway


OSR History

Navigating The Rails: OSR’s History and Legacy

OSR’s rich history is a testament to the vision and dedication of our founder and former president, Jeff Willsie. Since 1992, Jeff has been the driving force behind OSR, leading the company from a modest contract switching operation into one of Canada’s most dynamic and successful shortline railways.


Jeff’s love for railroading began during his teen years in St. Thomas, where his passion for the industry took root. He embarked on a lifelong career as a professional railroader when he joined CP Rail in Windsor. Jeff soon transferred to London where he qualified as a locomotive engineer. Jeff’s passion and expertise for the rails were undeniable.

The idea for the Ontario Southland Railway started when Jeff acquired Toronto, Hamilton & Buffalo diesel switcher 51. He also envisioned utilizing the Port Stanley Terminal Rail for freight service. On March 16, 1992, Jeff and his fellow investors formally incorporated the company. Although the vision for PSTR didn’t materialize, the acquisition of No. 51 opened doors to contract switching operations in Clarkson, Ontario.


The Clarkson operation played a pivotal role in establishing OSR’s reputation as a responsible operator, leading to two significant expansions within the next four years. In 1998, OSR commenced operations on the Guelph Junction Railway and the Canadian Pacific Railway Port Burwell Subdivision between Ingersoll and Tillsonburg. This agreement expanded in 2009 to include the CP St. Thomas Subdivision between Woodstock and St. Thomas, in addition to switching operations at GM’s CAMI Assembly plant and interchange traffic to and from CAMI and CN at Ingersoll.


Under Jeff’s visionary leadership, OSR earned and maintained a distinguished reputation for providing exceptional customer service and investing in infrastructure and equipment. Jeff cherished relationships, whether with employees, business partners, or customers, treating them all with fairness and respect. His legacy lives on, through the company he built from the ground up.


Are you ready to explore how Ontario Southland
Railway can optimize your transportation needs?

Get in touch with our team and discover the possibilities. Whether you have
questions, require a quote, or want to discuss your specific requirements, we’re
here to assist you. Let’s embark on a journey of efficiency and growth together.