125th Anniversary


Orr Insurance and Investment Celebrates 125 Years


2020 marks 125 years of Orr Insurance & Investment protecting people in Stratford and surrounding communities.

Born from a passion of civic duty and community improvement, R.Thomas Orr founded the business in 1895 with the values of being involved and giving back to the community. He understood the importance of protecting your loved ones, ensuring your livelihood, and building a financial future for years, decades and generations ahead.

R. Thomas Orr opened his office at 21 Downie Street with his sister Sarah and his niece Florence as his assistants. His original insurers were The Waterloo Mutual Fire Insurance Company and the Perth Mutual Fire Insurance Company. The two companies eventually amalgamated to become part of the Economical Mutual Insurance Company which is still represented today.

In 1921, Thomas Webster Orr came to work for his father introducing the second Orr generation to the business.

R. Thomas Orr (Tom Orr IV) became the third generation at Orr Insurance in 1956. This is also the year the business moved into 50 Cobourg Street, the Orr family home built in 1874 by the first Tom Orr where Tom Orr IV was born and raised. Orr Insurance and Investment’s Stratford office still operates from this location.

Jeff and Rick Orr bought the business from their father in 1999, becoming the fourth generation in the family business. In 2013 they signed a deal with the Huron Insurance Managers Group, bringing five new brokerages into the Orr family. There are now six locations, including offices in Stratford, Blyth, Brussels, Goderich, Linwood and Seaforth with over 65 dedicated insurance professionals.

Community involvement is something R. Thomas Orr set as a priority as early as 1895 and that commitment has transcended through each of the four generations. The Orr family has been involved with Stratford’s remarkable parks system since it was founded in 1904. R.Thomas Orr was a founding member of the Parks Board and led the campaign against the rail yards in the park system in 1913. He served on the Board until 1967, Tom Orr IV served from 1970-75 and now Rick is in his 20th year on that same Board.

Jeff has been involved with The Stratford & District Chamber of Commerce, the Library and the Stratford Economic Development Corporation. Tom Orr IV was known for his long term commitment to the Stratford Festival as its longest standing board member and past chair, a remarkable 18 years.

Orr Insurance & Investment continues to grow by investing in their staff and in each of their communities. They invite you to help celebrate their first 125 years in business at one of their many family friendly events this year.

“Orr Insurance & Investment - You’ve got Options”