
Photo: Town of Milton
It’s Street Name Monday!
On a weekly basis, we speak with local historian John Challinor II to gather information and details about the namesakes of our roads. If you weren’t aware, he and the late great historian, Jim Dills, wrote the book on Milton street names, writing Milton Streets back in 2007. Challinor also served seven years as the President of the Milton Historical Society.
Recently, we focused on Fiddlehead Lane and Fireweed Gate. This week, we’re covering Dockray Drive and Maddocks Trail.
Starting alphabetically with Dockray, Challinor says the name comes from a former community leader-turned-soldier who died during World War 1.
He adds that Dockray was an older soldier, joining the war at nearly 38-years-old. He was killed in September 1916. Challinor calls Dockray’s death a major loss for the community at that time, as Milton was sitting at roughly 1500 people.
You can find Dockray’s name on the Cenotaph in Milton.
Our other street this week is Maddocks Trail. The namesake also enlisted in the war, but had a bad spell of luck that led to his eventual death upon return.
Challinor theorizes that Maddocks’ fall, and subsequent head injury, in 1912 might have led to him being sidelined in the war as a blacksmith. It was severe enough that he eventually died from the injury just eight years later.
If you’re looking to understand how Milton’s streets are named, you should check out the book written by Challinor and Dills. Published by the Milton Historical Society back in 2007, it sold out in about six weeks and has since been long out of print. That said, according to Challinor, you can still find a copy at the Milton Public Library. With nearly 15-years having passed since the initial publication, and the extensive town growth in that time, an updated book is likely to come.
You can also take a walk with the late Jim Dills down Milton’s Main Street in 2002.
Have a suggestion on what you’d like to learn about next week? Let us know! We’re currently working on names that we find interesting. You can message our X account or email us at News1013@LocalRadio.ca. Otherwise, we’ll just continue asking about local street names that we find interesting.
If you have a news tip or story idea, you can now send us a heads up via email at:
- News1013@LocalRadio.ca (Milton)
- News1015@LocalRadio.ca (Orangeville)
- News92@LocalRadio.ca (South Simcoe)
- Rick.Sargent@LocalRadio.ca (Bolton)
If you’d like to get ahold of me personally, shoot me a message at Cameron.Wilkinson@LocalRadio.ca. We’re in the business of content creation, so no idea is a bad idea.







